key west sunset sailboat

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KEY WEST SUNSET SAIL with LIVE MUSIC

Come sail along on an ocean breeze and enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun. You’ll eat, drink and party the night away on Key West’s original live music sunset sail. So, grab someone’s hand and let the music move you as we chase down the world famous Key West sunset.

Check-In, 5:30pm
Departs, 6:00pm

Commotion On The Ocean Sunset Sail

Key West’s Original Live Music Sunset Sail

Check-In 5:30pm
Departs 6:00pm

Guests (Ages 4-10)

Flexible & Refundable Reservations. Guaranteed best price when you book direct. *Seasonal discount restrictions apply.

DEPARTURE POINT

Aerial view of Fury Catamaran sailing the ocean and carrying guests with Key West sunrise on the horizon

Trip Features

World-Famous Key West Sunset
Hot & Cold Appetizers
Private & Wedding Charters Available Learn More

What's Included

Ice Cold Margaritas
Draft Fury Lager, Michelob ULTRA & Seasonal Beer
Wine (Chardonnay, Pinot Grigio & Cabernet Sauvignon)
Sodas & Water

What to Bring

Valid, Government Issued Photo I.D.
Gratuities Customary

Guests partying in Key West aboard Fury's Commotion on the Ocean sunset cruise with strobe lights and the ocean behind them.

“ Commotion on the Ocean was a wonderful experience. The crew was absolutely fantastic! There was no need to worry about your cup ever being empty. The team was there before you could empty it to fill it back up. The ride was smooth, band was fantastic and the sunset was beautiful.”

This is a 10 out of 10!! It was an awesome day, professional, friendly staff all the way around! Thanks for a great day in Key West!

“ The crew, drinks and appetizers along with the live music made for a wonderful evening. Would definitely recommend Fury and Commotion on the Ocean to everyone!”

“ What a fun evening! The food was great, the band was great and the crew was even better; headed Captain Willie! I highly recommend Commotion on the Ocean, for a spectacular sunset cruise!!”

“ Commotion on the ocean was a great time. Fun music, excellent service, and beautiful views. Highly recommend!”

“ The Commotion On the Ocean was absolutely beautiful! Great music, dancing, tasty snacks, magnificent margaritas and an awesome catamaran! The sail ship was so much fun that we want to repeat it again once we return to Key West!”

“ This was our first Commotion on the Ocean and will most definitely become a must do every visit to Key West. EVERY staff person was over the top in customer service. Always smiling, taking care of any needs and best of all making sure your drink was always topped off. The food was plentiful and very good (loved the meatballs) And the live music was the perfect compliment to the entire experience. Great job Fury, I’ve ahead recommended you and will continue to do so!”

Mojo Seasoned Chicken Tenders
Shrimp Cocktail with Cocktail Sauce
Fresh Vegetables with Ranch
Jalapeño Cilantro Hummus
Smoked Fish Dip
Assorted Cheese & Cracker Platter

Chef’s seasonal selection of appetizers are subject to change

Selection of Sodas
Draft Fury Lager, Bud Light & Seasonal Beer

Menu Disclaimer

Unfortunately, we are not able to provide alternative menu items for those patrons who adhere to a specific diet or those susceptible to food allergies. Please feel free to contact us for details concerning our menu offerings should you have any questions. If you have any further reservations, we encourage you to bring a pre-packed meal of your own choosing.

BOAT FEATURES

State-of-the-Art Catamaran (65ft)
Large Seated Sundeck
Shaded Lounge Area
Modern Marine Restrooms

COMMOTION ON THE OCEAN KEY WEST SUNSET SAIL with LIVE MUSIC

Sail into the World Famous Key West Sunset aboard a FURY Catamaran!

Image of Fury catamaran sailing into Key West sunset

Historic Seaport

Located on the corner of Greene St. and Elizabeth St.next to The Conch Republic Seafood Company.

Commotion on the Ocean Live Music Sunset Sail
Champagne Sunset Cruise

Double Dip Snorkel Trip

Double Dip Combo
Island Adventure
Island Adventure Combo
Ultimate Adventure H2.0
Dolphin Watch & Snorkel
Dolphin Watch & Snorkel Sunset Combo

Watching the sunset from shore is beautiful but a Fury Sunset Sail is a very unique way to watch the sunset while being on the water, listening to live music, hot and cold appetizers and unlimited drinks.

The sunset time varies every day throughout the year. But don’t worry, we will make sure you see the sunset before heading back to shore.

We serve a seasonal selection of hot and cold appetizers that include:

(Menu is subject to change)

Yes! We serve water, sodas, margaritas, champagne, beer and wine.

The live band is dependent by the day. The music is an eclectic mix of songs and styles. It is a wide range of popular cover songs. There is something for everyone to enjoy!

The exact location and route of your sail is dependent upon the wind and marine conditions. Your captain will choose the route that allows for the best view of the sunset. You will most likely sail by Mallory Square, Sunset Key and the Key West Harbor.

All of Fury’s sunset sail trips are family friendly. The Commotion on the Ocean has a very lively atmosphere. If you would like a more low key excursion, we suggest the Champagne Sunset Cruise or the Glass Bottom Boat Sunset Cruise .

There are three multiple viewing decks on the sailing catamaran.

Yes, but the space is limited in the shaded areas.

Fury Water Adventures does not operate in unsafe weather conditions, but a light rain shower is not a deterrent. The Captain will assess the weather and should the Captain determine that the conditions are unsafe to run the tour, the tour may be postponed or it will be canceled. If a trip is canceled by Fury Water Adventures for any reason, every effort will be made to reschedule the trip during your stay in Key West. If you are unable to reschedule, you will have the option of receiving a voucher for a future trip or receiving a full refund. Every effort will be made to run tours, as advertised. Should Fury have to amend or alter your tour due to extraneous circumstances, tickets remain non-refundable on tours taken.

Departure Location #3 631 Greene Street – Located on the corner of Greene St. and Elizabeth St. next to The Conch Republic Seafood Company.

No, we do not provide parking at any of our check in locations, but you can use street parking, pay to park lots or parking garages.

All cancellations must be made at least 24 hours prior to your trip’s scheduled departure time. To place a cancellation, please call 1-888-976-0899 or email [email protected] and refer to the confirmation number at the top of your confirmation document. Failure to place a cancellation at least 24 hours in advance will result in your credit card being charged the full amount of the reserved. No refunds will be issued for reservations cancelled within 24 hours of departure, unless reservation refund protection was purchased. Please note that failure to show for the reserved trip without cancellation will result in no refund. If a trip is cancelled by Fury Water Adventures® for any reason, every effort will be made to reschedule the trip during your stay in Key West. If you are unable to reschedule, you will have the option of receiving a voucher for a future trip or receiving a refund.

Fury has a 24 hour notice cancellation policy to receive a refund. Guests can purchase Reservation Refund Protection for a 10% fee to be eligible to cancel or transfer tickets up to 1 hour prior to their scheduled departure. All you have to do is email a request to [email protected] no later than 1 hour in advance of your reservation time.

Reservation refund protection fees are 100% non-refundable in the event of any cancellation or reservation change.

Yes! Fury operates 365 days a year. Be sure to check out our Special Trips & Events page to see if we are running any special Holiday trips.

It is necessary for Fury to check you in and give you a boarding pass. This helps us maintain an accurate count for the coast guard. You may also be required to fill out various liability waiver forms for the activities you participate in.

No, we do not offer any wifi on our vessels.

Please bring a Valid Government Issued Photo ID. Gratuities are customary.

You may bring your own food and non-alcoholic drinks as long as there are no glass containers and it fits in a small soft cooler.

Yes! To receive a military discount on any Fury trip, please book through the MWR office on Key West’s Sigsbee base by calling (305) 293-4174. The ticket buyer must purchase tickets in person and present a valid Military Issued ID.

Most Fury tours will require the minor guest’s natural parent be present at check in to sign them in. Please call 888-976-0899 for specific policy details for your preferred tour.

Yes, life jackets are onboard for everyone in case of emergency.

Fury allows service animals only. A service animal is any dog that has been trained to perform tasks to benefit an individual. The work performed must be directly related to the individuals disability. According the ADA service animals for emotional support, therapy, comfort or companionship are not considered service animals.

The guest requiring the service animal must be in possession of the animal at all times. Due to the nature of Fury tours, guest and service animal may be required to remain on the boat for the entirety of the tour . This is to ensure the guest’s safety as well as that of the service animal, Key West wildlife, other guests, captain and crew.

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TRIP DETAILS

key west dolphin watch and snorkel during relaxing vacation

Dolphin Watch Eco Tour

Founding member of NOAA Dolphin Smart Program

Departs 9:00am, 12:30pm & 5:00pm

Fury catamaran out in the ocean with guests leaning over railing to view a group of dolphins swimming nearby.

Dolphin Watch Sunset Cruise Combo

Eco Tour • Backcountry Snorkel • Sunset (Available Seasonally)

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Fury’s Island Adventure Eco Tour

Remote Sanctuary Reserved For Locals

Departs 10:00am & 3:30pm
Food & Beverages

Save up to $13*

Glass Bottom Boat

Taking Visitors To Key West’s Reefs For Over 70 Years

Departs 12:00pm, 2:00pm & 6:00pm
Approx. 2 hrs

Save up to $6*

Aerial view of the ocean and a Fury glass bottom boat carrying guests on both top and bottom decks. Behind them is an island with homes and palm trees.

Glass Bottom Boat & Sunset Cruise

Island Adventure & Sunset Cruise Combo

Eco Tour • Snorkel • Kayak • Paddleboard • Sunset Combo Option

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Key West Jet Ski Tours

Brand New SeaDoo Jet Skis

Departs 8:30am-5:30pm

Key West Parasailing

Tandem + Triple Rides Largest Parasailing Fleet in Key West

Departs 9:00am-3:00pm, 4:15pm, 5:15pm & 6:15pm

Key West Private Charters

Completely Customizable

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Departs 10:00am & 1:00pm

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Reef & Ritas Snorkeling Trip

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Ticketed Cruises

Offering our most premium sailing experience, you are sure to create a memory that will last a life time. Step aboard for a classic day sail, sunset sailing, full moon cruise, or one of our special Holiday events. Learn more »

Sunset Sail

The BEST Key West sailing adventure is aboard the Schooner America 2.0! Join us aboard this stunning sailboat, and cruise with us into the magical Key West sunset! Learn more »

Private Yacht Charters

The Schooner America 2.0 is classically designed for a contemporary experience. This is the perfect vessel that offers an elegant atmosphere for you to host a Nautical Wedding, Corporate Outing or Team Builder. Learn more »

Key West Sunset Cruise just got upgraded….

Stargazing Sail»

Schooner America 2.0 is hosting enchanting evenings of stargazing in Key West!

Sunset Sail»

Schooner America 2.0 is sailing the emerald green waters of Key West! Step aboard this stunning sailboat, and cruise with us into the magical Key West sunset!

Soak in the sun and join us for an afternoon sail on the emerald green waters of Key West.

Sailing Season»

Schooner America 2.0 starts sailing on November 13th! Grab your tickets now!

Key West Full Moon Sail»

Join us for an evening out on the water for a Full Moon Sail on Schooner America 2.0!

SEE MORE TICKETED EVENTS

Classic Harbor Line: Key West

Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessel in the local Key West fleet: Schooner America 2.0 . While visiting Key West, Florida you will find a number of land and water based activities. However, a classic schooner sail, whether it be a day sail, or sunset sail, is well known to be the quintessential Key West activity that will highlight your stay and be the lasting memory forever.

South Florida sightseeing is all about getting on the water, seeing the wildlife, watching the Key West sunset with a loved one, and experiencing the adventure sailing in the great Key West Florida breeze. A 2 hour sailboat ride is a great way to take advantage of your time in Key West to enjoy all of these things.

Whether buying tickets for one of our Champagne Sunset Sails, Afternoon Key West day sail, Full Moon, Star-Gazer Sails; or Privately Chartering the schooners for a special family event or corporate event, you will be amazed by America 2.0’s beauty and comfort. It is maintained by the same creators of Key West’s former pride, Schooner America.

Classic Harbor Line is not only known for operating with amazing sailboats and classic yachts in Boston, New York, Newport, and Key West, but they are also renowned for their outstanding hospitality and customer service. You will find your captain and crew extremely capable, accommodating, helpful, and friendly whether you are spontaneously buying tickets for a classic day sail or planning your one-of-a-kind wedding day.

JOIN OUR MAILING LIST

See our calendar of events, private yacht charters.

Sail out into the emerald green waters of Key West and impress your guests. Step aboard the legendary Schooner America 2.0 for a private charter. This yacht is perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

PUBLIC EVENTS

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

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Contact Classic Harbor Line: 305-293-7245
Tickets: 305-293-7245

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Schooner spirit of independence sunset sail key west, our key west sunset sail cruise.

Trip Details

2 hour sunset sail aboard the classic sailing schooner Spirit of Independence
Friendly and attentive crew
Complimentary champagne, mimosas, fine Italian wines, and assorted beers
Delicious turkey focaccia sandwiches served fresh from Duetto’s Restaurant

Trip Highlights

Enjoy complimentary food and beverages served by our lovely crew
Guests are welcome to help raise sails or sit back and watch our expert crew
Listen to the wind fill the sails as we glide through the water propelled by the breeze
Hear captivating stories from Captain Ricky and the crew about the islands as you sail past points of interest
Soak up the breathtaking views of a Key West sunset and enjoy the magnificent afterglow of twilight as we cruise back to port

Our Promise is an Enjoyable Experience

Spirit of Independence is conveniently located in Old Town Key West in the Historic Seaport.

Our sailing adventures begin off the docks located behind local-favorite Schooner Wharf bar .

We are NOT a loud booze cruise or party boat. We aim for a true Key West sailing adventure,

The Spirit of Independence is licensed by the U.S. Coast Guard to carry 49 passengers. However, we limit our cruises to approximately 26 passengers , so it’s never crowded. That way, our roomy decks allow for plenty of seating, and for you to walk around and explore the ship while sailing. The steel hull makes her very stable – providing a smooth sailing experience, not a rocky boat ride.

We love both public and private cruises, as we enjoy getting to know our guests. Public walk-ons allow us to meet and make new friends. A private sail aboard Schooner Spirit of Independence creates the perfect venue for private events, weddings , corporate events, parties, and all types of social functions. Our professional crew make excellent hosts and will provide you and your guests with five-star service.

There’s something about a beautiful sunset that makes the perfect end to a perfect day in paradise. Here in Key West, many people find themselves on a sandy beach or a fishing pier trying to catch that perfect view. But take it from us… There is nothing quite like a sunset as seen from the water. While aboard our schooner, you will see the sunset as it stretches across the sky and reflects onto the vast surface of the water, and finally disappearing down into the sea.

Real. Fun. Sailing.

For the love of sailing.

‍ Sunset Sail Key West is more than just a private sailing charter, it is the culmination of decades of experience and a lifetime of passion for sailing, and for Key West. Our top priority is sharing the joy of boatmanship with our guests. We love making new friends and hopefully inspiring a few new sailors along the way. It is our mission to offer authentic sailing experiences around Key West, away from the crowds and noise of party boats and booze cruises.

Early Days... ‍ ‍

Around the turn of the century, a boy named Seth discovered he had saltwater running through his veins. After finding his way to the docks of Key West, he worked mornings before school cleaning boats and got to know the local sailors. Before long, at 14 years old he was crewing on High Tide with Captain Pam. His love of sailing was boundless, and by the time he was 17 he had embarked on his first transatlantic crossing. At 19, he became the youngest schooner captain in North America.

A Charter is Born

Captain Seth spent years sailing professionally throughout the eastern seaboard and Caribbean, across the Atlantic to the coast of Italy, and even through the Panama Canal. In 2010, after purchasing Conch West on a whim and restoring her for a year, he registered her as a charter boat, and Sunset Sail Key West was born. One day, upon spotting the High Tide dry-docked in Key West and close to ruin, he vowed to restore his old friend to her former glory. After a labor of love restoring her from the ground up, she joined the fleet.

The Fleet is Complete

In 2000, the first time Captain Seth laid eyes on When and If, he had an instant crush. Every few years, in one exotic place or another, he would cross paths with the schooner and take note. In June 2013, Captain Seth was hired to Captain When and If, followed by overseeing her meticulous 18-month long restoration. When the opportunity to purchase the historic yacht came up, there was no question. It was a great honor to keep her in America and to share her with the public as a charter. She is the crown jewel in the Sunset Sail fleet.

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

Friends of SSKW

Legal & safety.

The 8 Best Sunset Cruises in Key West (2024)

What better way to experience the majestic beauty of the Florida keys than by enjoying some of the best sunset cruises in Key West. Enjoy a fantastic Key West sunset with live music and bottomless booze with several different sunset cruise operators to choose from.

There are plenty of options for the best sunset cruise in Key West, with many providing drinks, snacks, or dinner as you take in the sunset. The most popular options are watching the sunset on a catamaran, listening to a live band, hoisting the sail and enjoying the best of Key West.

Top Pick: Key West Sunset Cruise

Don’t miss one of the highest-rated Sunset Cruises in Key West with over 2000 positive reviews and our top choice of the best sunset cruise in Key West !

Meeting Points & Information

Most of the Key West sunset cruise meeting points are Key West Historic Harbor or near Conch Republic .
The minimum drinking age is 21 years old .
The time of sunset in Key West varies throughout the year, but you can expect boat departures between 6 pm and 8 pm.

1. Key West Sunset Champagne Catamaran Cruise

4.5 Stars (449 Reviews)

Sebago has operated its Key West Sunset Champagne Catamaran Cruise for a number of years and is one of the top-rated Key West sunset cruises. Experience a 69-foot catamaran with an open bar that includes views across the Gulf of Mexico & Atlantic Ocean.

The hugely popular tour offers a hugely enjoyable Key West cruise experience, with a fantastic crew and captain who are eager to answer questions and point out sights of interest. Savor the spectacular sunset with either a beer, glass of champagne, wine or sangria.

Included in the tour:

Unlimited wine, beer, soft drinks
A modern catamaran
Tour length: 1 Hour & 30 Minutes – 2 hours.

What Guests Said:

“I had an absolutely amazing time! The views were breathtaking, the crew was exceptional, and the overall ambiance was magical. The sunset was a sight I will cherish forever. I highly recommend this cruise to anyone visiting Key West. Thank you for providing such a remarkable experience!” Joonhyeong_P

2. Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

4.5 Stars (372 Reviews)

Relax on a catamaran and enjoy some of the best sunset cruises in Key West.

Enjoy a cruise on a spectacular Key West catamaran with departures either in the morning or late in the evening for a sunset cruise.

The Key West Dolphin Watch Sunset Sail is an intimate sunset cruise that sails past the landmarks of Key West and takes in stunning views of Fort Zachary Taylor , as well as spotting wild dolphins in the Gulf of Mexico.

Enjoy the Key West sunset from the catamaran as you enjoy freshly prepared tapas and snacks. This Key West sunset cruise is perfect for anyone looking to sit back and relax, perhaps even spot dolphins and enjoy conversation with fellow passengers.

Included in the tour:

Small Groups
Departures from Key West Historic Harbor
Tour length 2 Hours 30 Minutes

Price of Cruise: $92 per person.

“ Aside from the amazing sail, the chats with the crew and other passengers was really an added highlight. We love being on the water and sunset did not disappoint – we also got to see some dolphins, but, being able to talk to the entire crew and some passengers really did add to the overall experience. Highly recommend this experience. Captain Rachel was phenomenal and we thoroughly enjoyed it .”

3. Key West Premium Sunset Sail aboard Schooner with Hors D’oeuvres and Full Bar

5 Stars (442 Reviews)

Unlike several of the other Key West sunset cruises which take place aboard a catamaran, sailing on a classic schooner is a completely different experience .

The classic schooner offers visitors a romantic vessel to enjoy watching the spectacular Key West sunset. With gorgeous hors d’oeuvres provided as you sail around iconic Key West landmarks such as Mallory Square which also happens to be the birthplace of watching sunsets in Key West.

Take in the sights and even help the crew hoist the sails on this classic Key West Schooner . The romantic sunset cruise on Appledore Star is one of the best sunset sail Key West tours.

Included in the Key West Sunset Cruise:

Tasty finger food
Hoist the sails with the crew
Tour length: 2 hours

What Guests Said:

“Great crew, just the right amount of time and beautiful sunset. The hors’d ‘oeuvres were tasty and lots of drink options. Champagne at sunset was my guilty pleasure! We’ll book again next time we visit!”

4. Key West Sunset Cruise with Tropical Buffet Dinner

4 Stars (961 Reviews)

Spend your late afternoon enjoying the infamous Key West Sunset with a tropical buffet dinner . The menu changes regularly but can expect to find typical dishes that are influenced by the region, such as black beans and rice, or Caribbean roast pork . Don’t miss trying the plantains!

With the weather in Florida sometimes being overwhelmingly hot, you can relax in the large open cabin that is able to fit 60 people comfortably with AC . When you’ve finished dining on the scrumptious buffet dinner, head to the deck, listen to the live music and enjoy the incredible sunset.

With an open bar that includes mojitos, what better way to enjoy one of the best sunset cruises in Key West than by sitting on a 65-foot yacht and making new memories.

Tropical buffet dinner
Air Conditioning
Spectacular Key West sunset views

Price of Cruise: $88

“The food was amazing!! The service outstanding! Entertainment was great and funny! The performer engaged the crowd and was family friendly.”

5. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres

4.5 Stars (2229 Reviews)

One of the top-rated and best sunset cruises in Key West is the Key West Sunset Sail with Full Bar and Live Music. Set sail in the late afternoon and enjoy terrific live music, a full open bar, and plenty of delicious hors d’oeuvres.

It also happens to be one of the busiest booze cruises in Key West that has a solid reputation for its energetic crew and entertainment. Dance the evening away while enjoying a full open bar that includes beer, sodas, wine and sparkling wine.

The hors d’oeuvres are tasty finger food staples such as egg rolls, shrimp and other great food for soaking up all the booze!

With live commentary and information about the island of Key West, the Key West cruise takes in the landmarks of Key West and one of the most spectacular sunsets in the Florida Keys.

Hearty snacks

Price of Cruise: $80

“Live music, good appetizers and great crew! We had a blast! We’d do it again and recommend to anyone especially couples.”

6. 2-Hour Private Sunset Cruise around Key West

4.5 Stars (46 Reviews)

Want to escape the crowds and charter your own private sunset cruise in Key West ? Then Blue Chi Charters offers an incredible and intimate experience. Experience the incredible Key West sunset with just your loved ones, as you spend 2 hours passing by the iconic Key West landmarks.

Savour the privacy and experience Key West without the crowds, as you head to points of interest like the Southernmost Point in the USA, or uninterrupted views of Fort Zachary Taylor State Park & Mallory Square.

You can enjoy your private sunset cruise in Key West with complimentary beverages. You can also bring your own bottles of wine and beer on board as they have an ice cooler.

Private Charter Boat
Bottled Water

“I took my significant other for a private, romantic cruise into the sunset and we had a wonderful time on this two hour ride around Key West. Our Skipper was very knowledgeable and kind, he provided interesting insights at just the right moments without being intrusive. It was a truly romantic and memorable experience that ended with a spectacular sunset.”

7. Key West Sunset Snorkel with Unlimited Draft Beer & Wine

4.5 Stars (76 Reviews)

Set sail and explore the incredible crystal clear waters of Key West, stopping off for snorkeling and swimming in the waters of the Atlantic Ocean . Experience the magic of the coral reefs that are abundant with marine life.

Spend the hours before sunset swimming the 3rd largest natural reef in the world, the Florida Marine Sanctuary. Keep your eyes peeled for turtles, reef fish and you may even spot a wild dolphin!

Back on board, enjoy the amazing Key West sunset with a nice cold beer or glass of wine as your dry off. This is one of the best sunset cruises in Key West for visitors looking to swim and enjoy a spectacular sunset.

Included in the private catamaran:

Snorkeling equipment
Open water snorkeling in a coral reef

Price of Cruise: $60

“The crew made the experience easy and super enjoyable. The tour isn’t crowded and comfortable. Definitely recommend this one out of all the tours in Key west!”

8. Sunset Tiki Boat Tour in Key West

5 Stars (93 Reviews)

If you are in Key West with a group of friends, what better way to enjoy the amazing sunset in Key West than by renting your very own Tiki Boat ?

Bring your own booze as you and your friends set sail on a tiki boat complete with a tiki bar!

“What a great night! Very fun to be on the water on this boat! Nick the captain was personable and fun! We brought our white claw and snacks! We will book this again!!”

A Key West Sunset Cruise You Won’t Forget

Why not take the hassle and claustrophobia out of watching the Key West sunset by taking a splendid and squish-less experience of a fabulous Key West sunset cruise?

Drop a comment below and let me know which of the best sunset cruises in Key West you ended up choosing and how it was! Continuing on your Florida adventure? Make sure to check out my post on the best rooftop bars in Tampa .

Pin for Later!

Meet Missy…

Missy spent the first 2 decades of her life living in her native Dublin, Ireland. Before a life living overseas called to her, and she spent the next decade living in China, Laos & Belgium. She now splits her time in Antwerp, Belgium, and wherever the sun is currently shining. You can follow Missy’s real-time travels on her Instagram .

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An Authentic Key West Sailing Experience!

Come sail Key West’s most photographed ship – the Jolly II Rover , a square-rigged topsail schooner! A Key West sailing adventure aboard the Schooner Jolly II Rover takes you back in time on a classic 80’ tall ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly II Rover.

Roling Thunder Happy Hour from James Papagno on Vimeo .

The crew from Active Perspectives and Bombarda Rum chose the Rover to set the stage for their latest investment video. They were kind enough to create a short director’s cut for us to use. Cheers gents! (see the full video here )

Sunset Sail

A top Key West attraction is the Jolly II Rovers famous “Red Sails in the Sunset” 2 hour sunset sail! Take in a memorable sail of Key West’s most famous sights while the sun works its magic turning the sky brilliant colors. With our distinctive red sails and being the only square rigged tall ship in Key West, the Jolly II Rover is the focal point as we sail past the Mallory Square Sunset Celebration. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic tall ship sailing experience.

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Key West Day Sail

Our daily 2-hour afternoon sailing tour fits perfectly into your Key West sightseeing trip. Enjoy an exciting Key West sailing adventure on the glistening crystal blue waters, with the Rover’s signature red sails flying! Look for the abundant Florida Keys wildlife both in the air and sea. Find your inner pirate and join the crew while you hoist the sails, steer the ship and fire the cannons!

Private Charters

Searching for a truly unique Key West sailing experience that is all your own? Charter your own private Key West tall ship sailing adventure. Whether its a few hours to celebrate a special event or an all day adventure, tell us where you want to go and what you want to experience, then climb aboard! For memories of a lifetime, charter a sunset wedding or an overnight excursion. Boca Grand is only 12 miles outside of Key West and is in a world of it’s own. You can even charter the Jolly II Rover for a private party dock side or anchor overnight experience.

Experiences

Key West Experiences

Key West Lighted Boat Parade

Join the Crew of the Jolly II Rover and parade through the Historic Seaport of Key West showing off the ships holiday décor! Enjoy a starry night, a festive atmosphere and thousands of twinkling lights on this entertaining evening cruise. Bring your own choice of food and beverages, bottled water snacks of crackers and cheeses included.

Key West Wreckers Race

The “day of wreckoning” reenacts times in Key West history when wreckers raced to a disabled ship, rescued the crew and laid claim to the cargo! Today, there is nothing to rescue except bruised egos from the last race. Join the Schooner Jolly II Rover for a day of rivalry, fun and radio insults on the high seas! Enjoy an exciting sailing adventure among a multitude of sailing vessels all competing for fun!

Key West Civil War Days

Join the crew of the Schooner Jolly II Rover for this very exciting and famous, annual Battle of the Schooners!! Re-enactors in period costume will be onboard as the Schooner Jolly II Rover defends its position in the harbor against opposing forces from both land and sea! This is a very popular and very exciting event. Seating will be limited to 16 passengers and ear protection will be provided to all passengers.

Currently operating year round out of the Historic Seaport of Key West, Florida, the Schooner Jolly II Rover is the only square rigged, topsail schooner contracted with the Florida National Boy Scouts of America High Adventure Sea Base Program. The Jolly II Rover provides boy scout troops with week long sailing, snorkeling and fishing adventures in the beautiful waters of the lower Florida Keys through the months of June, July and August.

Over the years, the Schooner Jolly Rover has been featured in countless magazines, newspapers and blogs for our iconic red sails and legendary sunset cruises. Read them here.

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Many locals as well as visitors are repeat sailors. And we love seeing familiar faces, so we offer $15 off your second sail and your third sail is FREE!

*Within 30 days.

Where to Find Us

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305-304-2235 BOOK ONLINE

Sunset Sails

Parasailing
Key West Private Charters

Land’s End Sunset Sail

$69.95 Regularly $79.95

2 Hours - With Live Music

SUMMER: 6:30PM WINTER: 4:30PM

Captain’s Choice Dolphin Watch & Sunset Sail

$79.95 Regularly $89.95

SUMMER: 6:00PM WINTER: 4:30PM

Catamaran Champagne Sunset Sail

$49.95 Regularly $59.95

Schooner Champagne Sunset Sail

Windjammer Classic Sunset Sail

WINTER: 4:30PM SPRING: 6:30PM

SUNSETS KEY WEST STYLE

A local saying in Key West is “see you at sunset.” Throughout Key West’s history, dramatic sunsets have weaved their spell over visitors. Watching the sunset has become an integral part of everyday life in paradise. Leave it to Key West to raise sunset watching to an art form with Mallory Square’s Sunset Celebration, now a top attraction in Key West. Sunset watching as an organized event started out casually in the late 1960’s as a group of free spirits started meeting nightly on the working docks at Mallory Square. Mallory Square has long been a focal point on the island, starting as a meeting place for pirates, dock for merchant ships, and now with its nightly celebrations.

What began in the 1960s as a group of 30-40 regulars gathering for sunset, grew over the years in numbers with a flea market feel. Docks were overwhelmed, nearby merchants complained, and a better solution was needed. So in 1984, the Key West Cultural Preservation Society (CPS) was formed. This not-for-profit corporation’s purpose is to support the arts by managing the Sunset Celebration, Key West’s funky nightly arts festival. To further its mission, the CPS rents space to artisans and helps “preserve the spirit of the Mallory Square Sunset Celebration, its history, tradition and reality.” Each night, a new celebration begins with the sun as star performer, painting the sky brilliant colors. Joining in the festivities are jugglers, musicians, artists, tourists, food vendors, locals, fishermen and even psychics, all mingling together on Mallory Square.

You may still be asking yourself, the sun sets everywhere, what makes a Key West sunset so special? That question is answered by experiencing it for yourself. The best place to watch the sunset in Key West is on the deck of a Sebago ship, drink in hand. Sebago takes part in this nightly sunset tradition, sailing past Mallory Square where our guests wave to the crowd gathered on the docks and watch the jugglers, musicians and other performers. Then we head for open water and sail into the sunset. As the orange sun sinks lower, casting its reflection on the turquoise sea, Sebago’s experienced captains carefully maneuver their ship to provide their guests with a magnificent view of the sunset. No need to stand on tiptoe to catch a glimpse over the crowds!

Sebago offers a variety of sunset tours on catamarans, historic schooners and even combo snorkel tours. There is sure to be one tailored to your interests and schedule. Book a Sebago Key West Sunset Tour and join in the celebration!

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Part of the Hindu Charters Family
(305) 509-1771
[email protected]

Argo Navis is a 75 ft luxury catamaran — the last commercial sailing vessel built in Key West, Florida. We sail year-round from the Key West Historic Seaport offering Sunset Cruises, Brunch Sails, and Day Trips as well as Special Events. All ticketed trips are inclusive of craft beers & cocktails, fine wines, as well as light bites & heavier menu offerings, depending on the trip. Our team specializes in creating and hosting your perfect Private Charter and the vessel is also available as a venue for corporate meetings, classes, summits & seminars.

Argo navis is part of the hindu charters family – sail as you are. .

Join us on the SV Argo Navis, the only luxury catamaran sailing yacht in Key West, for 2 hours of craft food and drink pairings as the sun sets where the Atlantic Ocean meets the Gulf of Mexico. Your sail through the enchanting changing tropical colors of the sky and water includes a selection of craft beers, fine wines, six rounds of charcuterie style passed appetizers and bean-to-bar chocolates chosen by our crew with suggestions from our sommelier. We don’t play any music and never overcrowd the boat so there’s a seat for everyone to enjoy space to stretch out and relax while experiencing the tranquility of a wind driven vessel. A sunset on the water is the original nightly show, and we’ve got the best front row seats.

The Argo also offers a Best of Key West Sunday Brunch, special themed and holiday sails, and private charters for your group or event. From weddings to corporate retreats, chef dinners to birthday and anniversary celebrations to dockside meeting venues, the crew is standing by to custom create your perfect excursion with exquisite attention to every detail.

Sail as you are on the 75’ luxury catamaran SV Argo Navis for an unsurpassed experience. Book direct here on the website or call 305.509.1771 for personalized assistance. Always friendly dog friendly on all our sails. Have more questions about our sailing charters? View our Frequently Asked Questions page here.

Have more questions? See our FAQ here.

What Do Our Guests Say?

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PART OF THE HINDU FAMILY

Hindu Charters is a family-owned, local business sailing out of both Key West, Florida and Provincetown, Massachusetts. Schooner Hindu, one of the oldest, most historic wooden schooners in the Florida Keys, has been sailing out of P-Town since 1946. Built in 1925, Hindu is undergoing a top to bottom historic restoration just in time for her 100 th anniversary. To help with this enormous undertaking, all sails on our luxury catamaran SV Argo Navis support this effort.

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The Keys Are Calling & We Must Go

Explore our tours, see the real keys.

Two schooners sailing at sunset near Key West, FL

Wind & Wine Sunset Sail

Sail, Snorkel & Kayak

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Private Charters

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We sail every day.

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Seasick? Not Likely.

We love calm water.

Key West Sailing Charters

What makes us different.

Locally owned and operated for more than 30 years, Danger Charters is all about the Key West sailing experience – wind in the sails, sun on our face, the sound of the waves lapping against the hull.

Our shallow-draft schooners allow us to go where others can’t … and we choose to go where others don’t. We seek calm, crystal-clear water so that you can enjoy the very best of the beautiful Florida Keys. We can’t wait to host you for an unforgettable day of sailing in Key West.

We treat you to the Key West that’s inspired countless paintings and poetry, and show you why locals choose Danger Charters too. Kick back, relax, and be one with the wind and waves … we’ll take care of the rest.

A Danger Charters crew member unties a rope

What We Provide

Calm water for smooth sailing
Excellent food and beverage
No crowds so you can lounge
Experienced captains
Knowledgeable crew
Eco-education opportunities
Top-quality snorkeling gear
Easy to use kayaks

Our Playground

Luke loves to be on the water and is super knowledgeable about the stunning marine life that surrounds Key West. Luke moved to the Keys from South Carolina a little over a year ago, so even when he’s not working he’s out exploring the Backcountry and waterways.

Meet the Crew

Historic Key West Schooners

Schematic of Danger one of the schooners in Danger Charters' Key West fleet

Danger’s Prize

Schematic of Pearl one of the schooners in Danger Charters' Key West fleet

Danger’s Pearl

Learn About Our Boats

Spent my birthday eve sunset sailing with my husband and it was unforgettable! Could not recommend it enough. Such a beautiful time! I would definitely do it again next time we go to Key West. Thank you all for such a wonderful and memorable experience!

Katherine Bejerano — Google

I can’t get over how personal this experience was!!! The group was small which made the experience that much better. Myself, my sister, and my two daughters had the best time! Everyone was so kind and personable! Thank you for a wonderful time! Danger Charters is definitely a must if you are looking for a sail, snorkel, kayak experience for the first time!

Carlota Castillo — Google

We did a full day sail and snorkel trip with about 27 of us and it was perfect! The crew Bryan, Logan, and Alex were informative, attentive, down to Earth, and make a mean pasta salad! They even provided the snorkeling gear and tips on where to look at the reef! Hands down the best trip during Key West! Will definitely book again in the future! Thanks guys!

Michelle Williams — Google

Make Memories To Last A Lifetime

And on a sailboat?! There’s no beating that! 😁 🌅 ⛵️ • #sailinglife #sailing #sunsetsail #visitkeywest #unlockthekeys #keywestsunset #lovefl #keywest #visitflorida #keywestlife #dangercharters

Our beautiful SV “Sarah” in all her glory 🙌🏻

Happy International Women’s Day 👸 Big thanks to our lovely ladies of the Danger crew! Couldn’t do what we do with out ya ;) • #sailinglovers #sailing #chartersailing #thefloridakeys #visitkeywest #keywest #visitflorida #dangercharters #boatlife #boatcharter #internationwomensday #boatgirl

🌅🌅🌅 • #sailinglife #sailing #sunsetsail #visitkeywest #unlockthekeys #keywestsunset #lovefl #keywest #visitflorida #keywestlife #dangercharters

Oh the things you can find on our kayak tour! Morgan here found this spotted sea hare on the sea floor! One of the funnier creatures we have down here because they will ink all over you 🤣 • #sandbar #boatlife #thingstodoinkeywest #visitkeywest #keywest #dangercharters

Escape the chaos of Duval Street and dive into the natural beauty of the Florida Keys! 🌴🛶 Kayaking through the mangroves is an absolute must-do! 🌿 Immerse yourself in nature’s sanctuary and get up close with diverse wildlife! • #boatlife #keywest #thingstodoinkeywest #visitflorida #mangroves #naturelovers #travellife #kayaking

Our online storefront is finally up and running, so be sure to check out our new Danger Merch! ⛵️ The link is in our bio! Also, since St. Paddy’s Day is approaching, we have created some themed clothing for the holiday 🍀💚🍻 • #dangercharters #keywest #visitthefloridakeys #islandlife #keywestmerch #keywestflorida #boatlife

Smiles & Sunsets 🌅 • #sailinglife #sailing #sunsetsail #visitkeywest #unlockthekeys #keywestsunset #lovefl #keywest #visitflorida #keywestlife #dangercharters

Ready to Start Your Adventure?

March Special – Save 15% off of all Day sails (AM, PM, and Premium) with code SPRINGSAIL15. Save 10% off the Wind & Wine sails with code LUCKY10. Not valid on private charters.

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Friends enjoy a glass of white wine while on a sailing charter with Danger Charters in Key West, FL

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Key West's #1 Rated Schooner Sails

Key west’s award winning schooner cruises, adventure awaits you.

Key West's #1 Rated Day Sail

Sunset Sails

Key west's award winning sunset sails.

Bugeye Backcountry Eco Tour

Private Charters

Charter our historic schooners, historic schooners, that honor the waters of key west.

Schooner Appledore II circumnavigated the world on her first journey. She continues to prove her seaworthiness as she makes the twice-a-year journey between Key West and Camden for daily sailing adventures.

Appledore Star is the last known Chesapeake Bugeye ever built. This unique shallow draft design allows her to navigate Key West’s backcountry with ease on daily eco-tours exploring mangrove islands.

Experience a Key West bucket list experience on one of our historic Schooners. Choose from our award winning Key West Sunset Sail, Key West Windjammer Day Sail, Key West Eco-Tour or start your vacation with our Key West Bloody Mary Sail.

Discover These Great Key West

Wooden schooners.

Step aboard the Appledore II for a true sailing adventure. This two-masted hand-built wooden schooner calls both Camden, Maine and Key West, Florida home. During warm weather months enjoy a scenic sail along Maine’s magnificent rocky coast. When the weather turns cold, the Appledore II heads south and sails Key West’s tropical waters.

see the schooners

Welcome back! We are pleased to announce our official re-opening on June 5th with reduced capacities and additional safety protocols to ensure a safe and enjoyable experience for both passengers and crew. Advanced reservations (book Online or Call) are required. No walk ups are permitted per the City of Key West at this time.

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The Best Florida Keys Sunset Cruises

O ne of the top things to do in Key West or on a Florida Keys Road Trip is to go on a Florida Keys sunset cruise. Being out on the water in the Keys is a must do and a sunset cruise is an awesome way to end your day!

So after relaxing on the gorgeous Florida Keys beaches , taking a snorkeling adventure, or kayaking in the Florida Keys end the day with a beautiful sunset cruise.

There are sunset cruises available in all parts of the Keys from the upper Keys to the lower Keys. Below we break out the Keys based on these locations to help you pick the right one for your trip.

Lower Keys Sunset Cruise Picks

There’s nothing quite like a Key West sunset, and Key West has a number of awesome Key West sunset cruise tours, including dinner cruises, eco tours, and even snorkeling cruises.

Sunset Watersports – Key West Sunset Dinner Cruise

Departure location: Key West, FL

Child policy: All ages welcome
Food and drinks included? Dinner and open bar included.

Fine dining is always appreciated when on vacation. This is especially true when the delicious food comes with an incredible experience, which is why we highly recommend the Key West Sunset Dinner Cruise offered by Sunset Watersports.

An amazing menu and open bar will keep you full and happy, and the spectacular sunset will provide you with plenty of entertainment on this lovely adventure.

Learn more about the Key West Sunset Dinner Cruise here!

Glass Bottom Boat Reef and Eco Tour

Food and drinks included? Water is available and included.

Like the pick at the very top of this page, this Florida Keys sunset cruise takes you out on a glass-bottom boat, giving you a chance to peek under the water at the beauty below.

Additionally, information is provided about the ecosystem of the area along the way, making for an even more interesting ride. Of course, a gorgeous sunset is the grand finale of this amazing tour.

Learn more about the Glass Bottom Boat Reed and Eco Tour here!

Sunset Watersports – Triple Combo Snorkeling, Dolphin, and Sunset Cruise

Food and drinks included? Beer, water, and soft drinks are included.

Want to do a little bit of several different things while out on the water? If so, the Sunset Watersports Triple Combo Snorkeling, Dolphin, and Sunset Cruise should be right up your alley.

Not only will you get to go under the water to see the wildlife there, you’ll also get to marvel over the beauty of dolphins in their natural habitat. At the end of it all, you can finish your cruise with an awesome sunset.

Learn more about the Triple Combo trip here!

Sunset Cycleboat Cruise

Child policy: Ages 21+ only
Food and drinks included? Water and ice are available and included.

An unusual option that we absolutely adore, this sunset cycle boat cruise is a bit of a workout and a whole lot of fun. Not only will you get the opportunity to help propel the boat by pedaling, you’ll also be surrounded by fun-loving folks just like yourself as you watch the sun paint colors across the sky and water as it sets on the horizon.

Learn more about the Sunset Cycleboat Cruise here!

Sunset Watersports – Sunset Snorkel Sail with Open Bar & Live Music

Food and drinks included? Open bar, soft drinks, water, and appetizers are included.

Lastly, we must mention this sunset snorkel sail with an open bar and live music offered by Sunset Watersports. This is another great option if you want a little bit of a lot of great things.

Try some snorkeling before grabbing a drink and an appetizer and then dancing the night away to some awesome live music as the sun sets over the water. If that doesn’t sound magical, we don’t know what does.

Learn more about this option here!

Fury Commotion of the Ocean

Food and drinks included? Seasonal Appetizers and Snacks

On the Commotion of the Ocean, you will enjoy music while being served ice-cold beverages including champagne, draft beer, wine, and non-alcoholic drinks. Eat, drink and party the night away as you see one of the best sunsets ever!

Learn more about Fury Commotion of the Ocean here!

Middle Keys Sunset Cruise Picks

If you find yourself halfway down the Keys, this is the section for you. These middle Keys sunset cruises leave from Marathon and other great locations, meaning you’ll have plenty to enjoy before and after your cruise as well.

Sailing Catamaran Sirius – Ocean Sailing Inc.

Departure location: Marathon, FL
Food and drinks included? No

Those looking to save a few bucks while still having an amazing sunset cruise experience should head over to Sailing Catamaran Sirius – Ocean Sailing Inc.

This awesome boat tour company offers a sunset cruise at a very affordable per-person price. This is the ideal pick for a budget vacation for sure! Experience the great sailing experience aboard this catamaran.

Learn more here!

Marathon Mermaid Charters

Food and drinks included? Champagne included

Marathon Mermaid Charters is a super fun company that takes guests out in their unique boat, which the owners of the company built themselves.

If that’s not enough to get you onboard, you should also know that the sunset sails offered by these folks include complimentary champagne and music, making the cruise experience a truly magical one.

Keys Boat Tours

Departure location: Ohio Key, FL
Food and drinks included? No, but you may bring your own.

A favorite of many who visit Ohio Key, Keys Boat Tours is definitely an awesome company. While this company doesn’t officially offer a sunset cruise, they are happy to book customized private charters and can definitely take you out to watch the sunset over the water.

Not only that, the captain is ordained and can perform wedding and memorial ceremonies at sea.

Private Snorkeling and Sunset Adventure

Child policy: Ages 3 and up welcome

Have you ever wanted to try your hand at snorkeling? Why not get two awesome experiences for the price of one by booking this amazing private snorkeling and sunset cruise?

Spend some time on this snorkel trip checking out the amazing fish and other animals that live in the ocean surrounding the Keys before admiring a gorgeous sunset.

Upper Keys Sunset Cruise Picks

The cruises below are in popular areas such as Key Largo, and are the perfect way to experience a Florida sunset without needing to venture to the bottom of the Keys.

Key Largo Princess Glass Bottom Boat

Departure location: Key Largo, FL
Food and drinks included? Available onboard, but not included.

The sunset tour offered by Key Largo Princess is extra neat because guests ride in a glass-bottom boat. This means you can see all the plants and animals below the water’s surface as you ride out to view the setting sun.

This can be especially cool in the late evening, as you might get an opportunity to see animals and dolphin watch that are not typically out during the daytime hours.

Pirate’s Choice Cruises

Pirate’s Choice Cruises is a fun company that gives guests the chance to be pirates for a few hours. Their sunset cruises take you out on their unique “pirate ship” to view the gorgeous sunsets that so many pirates before you once enjoyed.

Sit back and relax as your captain gives you a tour of the crystal waters of the Keys, matey!

A Family Fun Boat Tour Company

Departure location: Islamorada, FL

Looking for a Florida Keys sunset cruise that is made for families? Look no further than A Family Fun Boat Tour Company.

As the name suggests, this company is all about creating experiences for all ages, and their sunset cruises are neat because they can be customized to include sandbar stops, snorkeling, and departure times that work best for you.

AquaBlue Adventures Boat Charter

AquaBlue Adventures Boat charter is another great option in the upper keys. Once again, this company gives guests the opportunity to customize a lot about their sunset tour.

One of the coolest offerings they have is the ability to choose the type of boat you prefer. Options include a boat, a yacht, or even a party barge for those with large groups.

Where to Stay

Hampton Inn Key West enjoy a view of the ocean at this beachside hotel. Free continental breakfast and an on-site restaurant are just 2 of the many amenities offered at this family-friendly hotel.

Hyatt Centric Key West Resort & Spa This resort is located in the heart of Key West. Walking distance to many shops, restaurants, and other attractions.

Vacation Rentals

Beach Paradise in the Keys This great townhome is in the perfect location in the Keys, just 2 blocks from the iconic Duval Street. This home can sleep 8 and is filled with modern amenities.

Clearly, there is something for everyone when it comes to Florida Keys sunset cruises. Hopefully, we’ve helped you find the perfect option for your next trip to southern Florida, so you can fully appreciate those sunsets everyone loves so much.

When visiting Key West be sure you don’t miss the world famous Mallory Square sunset celebration too!

Make sure to pack a camera so you can try to capture a little bit of that beauty to take home with you! You will love your sunset cruises Key West!

The post The Best Florida Keys Sunset Cruises appeared first on Crazy Family Adventure .

Looking at going on a Florida Keys sunset cruise? Great choice! There are tons of amazing sunset cruise options. Check out our top picks.

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The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Tours of Key West three years running.

Rated #1 on Tours of Key West for three years running Beautiful sailing boat
Exclusive Trip with just over twenty passengers
Amazing Key West sunset views

Description

The Wind & Wine Key West Sunset Sail has been honored with the #1 rating on Tours of Key West for three consecutive years. Wind & Wine is an incomparable sunset experience amid the warm tropical caribbean waters of the Florida Keys.

Rated a Top Sunset Cruise in North America by Coastal Living Magazine, the Wind and Wine Sunset Cruise is unparalleled for folks who want an upscale, yet relaxed and intimate, sunset sail. Sailing nightly, we serve eight different fine wines from all over the world, usually four red, three white, and a Champagne.

Wine drinkers love this cruise, since it is virtually the only sailing excursion in the U.S. that serves “real” wine. In addition, an array of quality beer, and hors d’oeuvres are also served, making the evening an unforgettable start to a great Key West night!

Choose from up to 8 different types of wine from around the world (taste through them all, or focus on your favorites). Choose from 5 different types of imported and domestic beer. Enjoy a wonderful variety of delicious appetizers like Havarti Dill, Smoke Gouda and Summer Sausage, Caprese Skewers, Water Crackers with Brie, Green Apple with a Honey Drizzle, and more.

Reservations are REQUIRED for all bookings
Book Your Package On-Line and Receive Your Confirmation
Departure point: Detailed check-in instructions - including address, Google map, and parking information - will be included in your final confirmation email.
Duration: 2 Hours (approx.)
Check-in time: Please check in 30 minutes before the activity start time.

What's Included

Sunset Sail Aboard a Modern Style Schooner
Fancy Cheeses, Crackers and Fruit
Premium Wine
Imported and Domestic Beer
Sodas and Bottled Water

What To Bring

Confirmation Voucher (printed or mobile)
Any required or suggested items listed on your confirmation email.

Additional Info

Likely to sell out.

Spaces are extremely limited this time of year so book early to ensure the date you want.

Voucher Confirmation Info

This tour accepts both printed and electronic vouchers (e-vouchers). You can either print the voucher and present a paper copy on the day of travel. Or, if you travel with a mobile device, simply show your Photo ID and present your voucher on your Smartphone or tablet on the day of travel.

Local Operator Information

Complete operator information, including local telephone number, will be included on your Confirmation Voucher.

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

For a full refund, you must cancel at least 24 hours before the experience’s start time.
If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
Any changes made less than 24 hours before the experience’s start time will not be accepted.
Cut-off times are based on the experience’s local time.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Frequently Asked Questions FAQ

The answers provided below are based on answers previously given to travelers by the Tours of Key West customer support team.

What food and drink is served on Wind & Wine?

Choose from up to 8 different types of wine from around the world (taste through them all, or just choose your favorites).

Choose from 5 different types of imported and domestic beer.

Enjoy a wonderful variety of delicious appetizers like Havarti Dill, Smoked Gouda and Summer Sausage, Caprese Skewers, Water Crackers with Brie, Green Apple with a Honey Drizzle, and more.

Is there an age limit for the Wind & Wine Key West Sunset Sail?

Yes, there is. In 2017 the decision was made to disallow anyone 12 and under from Key West Wind & Wine Sunset Sail. The feedback on this move has been tremendously positive, as it is, after all, a wine tasting cruise.

What is the weather cancellation policy?

If the Key West Wind & Wine Sunset Sail must be canceled due to bad weather, and you cannot go on another day or time, you will be issued a refund by Tours of Key West.

Where can I park my car?

If required, parking instructions for the Key West Wind & Wine Sunset Sail will be included in your confirmation email.

Where is the meeting point for this activity?

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Key West Wind & Wine Sunset Sail will be included in your confirmation email from Tours of Key West. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

Key West, Florida Detailed check-in instructions – including meeting point address, Google map, and parking information – for will be included in your final confirmation email from Tours of Key West. Please be sure to double and triple check your email address is correct at checkout so this important email makes it way to you!

Average 4.94 out of 5 stars based on 1,076 traveler reviews collected by Tours of Key West and partner sites such as Cool Destinations and TripAdvisor

Still have questions?

We’re here to help. Call Us , " data-help-center="text-us"> Text Us , or Live Chat to speak with a Destination Specialist Product code: C-277559

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Tours of Key West wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

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The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Accessibility

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www.toursofkeywest.com
March 21, 2024

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Screen-reader and keyboard navigation.

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Keyboard navigation optimization: The background process also adjusts the website’s HTML, and adds various behaviors using JavaScript code to make the website operable by the keyboard. This includes the ability to navigate the website using the Tab and Shift+Tab keys, operate dropdowns with the arrow keys, close them with Esc, trigger buttons and links using the Enter key, navigate between radio and checkbox elements using the arrow keys, and fill them in with the Spacebar or Enter key.Additionally, keyboard users will find quick-navigation and content-skip menus, available at any time by clicking Alt+1, or as the first elements of the site while navigating with the keyboard. The background process also handles triggered popups by moving the keyboard focus towards them as soon as they appear, and not allow the focus drift outside of it.Users can also use shortcuts such as “M” (menus), “H” (headings), “F” (forms), “B” (buttons), and “G” (graphics) to jump to specific elements.

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(305) 697-1024

Explore the world with When and If

Welcome to the Schooner When And If. Built in 1939 for General George S. Patton, When And If was commissioned by Patton himself from naval architect John Alden, and built by FF Pendleton in Wiscasset, ME to sail around the world “When the war is over, and If I live through it.”

Experience the beauty of the water with our sailing excursions

Explore the water with our sister companies. Whether you're a seasoned sailor or a first-timer, our excursions have something for everyone.

Sunset Sail Key West

Sunset Sail Key West is more than just a private sailing charter, it is the culmination of decades of experience and a lifetime of passion for sailing, and for Key West.

Sunset Sail Salem

Salem and the North Shore are home to some of loveliest sailing in New England. We offer daily sailing and private charters on the beautiful Salem Sound.

Sailing on When and If

When And If sails all year round: out of Key West, FL in the Winter and Salem, MA in the Summer. With our wide range of custom private charter options as well as our a la carte shared sailing availabilities, you’re sure to find your dream sail on this beautiful classic schooner yacht.

Whether it’s a morning excursion, an afternoon on the water or a sunset sail, When And If offers an unparalleled sailing experience on a gorgeous historic schooner; see and be seen as you sail in style.

Experience the magic of sailing

Welcome to our photo gallery! We hope the photos inspire you to join us on one of our voyages and create your own unforgettable memories out on the sea.

The history of When and If

With her storied past, productive present, and bright future, When And If has a narrative all her own. She was commissioned by General George S Patton from the illustrious naval architect John Alden, and built by FF Pendleton of Wiscasset, ME to sail around the world “When the war is over, and if I live through it.”

Her sturdy construction of double planked mahogany over black locust frames and an oak keel made her heavier than Alden’s signature racing schooners, more suited to her transoceanic cruising agenda. She was launched in November of 1938 and in 1939 Patton took delivery of her to Massachusetts where the Patton and Ayer families lived. Shortly thereafter, Patton was deployed in Europe. He returned on leave at least once to sail the boat in his home waters of the North Shore of Massachusetts with his family. Many boats during World War Two, particularly wooden vessels, were requisitioned as sub hunters for the United States Navy though When And If seems to have escaped this fate and saw out the war in safety. Patton was killed in a car accident in Germany in 1945, shortly after the armistice, and his vision to sail around the world on the boat remains unfulfilled to this day.

When And If remained in the Patton family until 1972, when she was donated to the Landmark school for children with Dyslexia in Pride’s Crossing, MA. Patton himself was dyslexic and When And If’s time there marked some of the happiest years for children at the school. Today they come sailing and visit the boat both in Massachusetts and Florida, bringing their own families to regale them with their sea stories never forgotten from all those Summers ago.

In 1990 a vicious nor’easter tore When And If from her mooring and put her up on the rocks at Pride’s Crossing. She appeared mortally wounded, with a hole in her port side “you could drive a VW bug through” and all hope seemed lost until a pair of shipwrights from Martha’s Vineyard purchased the wreck and barged her over to Vineyard Haven to give her a new lease of life.

In 1994 to she was launched, sparkling, from the railway at Gannon and Benjamin, earning them industry-wide recognition for their fine craftsmanship and traditional values in shipbuilding.

Following a stint as the belle of Vineyard Haven harbour, When And If passed into private ownership for a time and in 2011 was purchased by Doug Hazlitt who, after his restoration of the Alden racing schooner Malabar X, purchased When And If prepared to undertake the second big rebuild of her life.

After X years, with a gleaming new sprung teak deck among the most prominent of her new adornments and her length restored to the original 63.5 ft from the 63 it had become during her previous rebuild, When And If once again splashed and lay in wait for her next adventure.

Captain Seth Salzmann had a special place in his heart for When And If. He remembers the first time he saw her in Penobscot Bay, ME in 2006 and though he knew almost every boat in those waters he didn’t recognize the new visitor. “It was like when you see a girl for the first time” he says.

In 2015, after he had managed a large portion of When And If’s 2012 refit, Seth couldn’t resist the opportunity to lease her and begin her new life as a sailing charter boat.

After a summer in Hyannis, MA and a winter in Key West, FL When And If spent the Summer of 2016 touring the Great Lakes for the Tall Ships Festival there before found her new Summer home the following year in Salem, MA.

During this time the opportunity arose for Seth to buy the boat and in 2017 he became owner/operator of his treasured vessel.

Seth’s ambition has always been to fulfil When And If’s destiny and sail around the world. Now with a young family in tow the focus is on keeping the boat busy and raising her condition, ready for that time in the not-too-distant future when her great journey will begin.

Check Out Our Holiday Specials!

Top 3 things to do in key west for your bachelor or bachelorette party.

guide to things to do for bachelorette party in key west florida

Experience Unforgettable Bachelor & Bachelorette Parties in Key West!

Are you planning the ultimate bachelor or bachelorette party in Key West, Florida? Look no further than Sunset Watersports for an unforgettable experience that combines luxury, adventure, and endless fun in the tropical paradise of the Florida Keys.

At Sunset Watersports, we specialize in providing private charters and group outings tailored to make your special occasion one for the books. With over three decades of experience, we are the leading watersports and activity provider in Key West, established in 1984 with a commitment to pioneering the industry and ensuring every guest has the time of their lives. Click here to check out our other private charter options

Top 3 Things To Do In Key West for Your Bachelor or Bachelorette Party!

Who We Are: Sunset Watersports

Sunset Watersports isn’t just another tour company – we’re a team of passionate individuals dedicated to providing unparalleled experiences for our guests. With a focus on fun, safety, and hospitality, we go above and beyond to ensure every moment with us is memorable.

Since 1984, we’ve been at the forefront of the watersports industry, constantly innovating and expanding our offerings to cater to the diverse interests of our guests. From adrenaline-pumping activities like parasailing and jet skiing to leisurely sunset cruises and eco-tours, there’s something for everyone to enjoy.

But what truly sets us apart is our commitment to customer satisfaction. From the moment you book with us until the last wave goodbye, our friendly staff is here to ensure your experience exceeds expectations. Whether you’re celebrating a milestone event like a bachelor or bachelorette party or simply seeking adventure in paradise, Sunset Watersports is your ultimate Key West companion.

So why wait? Start planning your dream bachelor or bachelorette party with Sunset Watersports today and create memories that will last a lifetime. Contact us now to reserve your private charter or group outing, and get ready for the adventure of a lifetime in Key West!

Next Key West Tip: Top Free Things To Do In Key West On Your Birthday

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Ultimate Sandbar & Kayak Eco Adventure

Join us for an exciting guided kayak tour through the mangrove islands! Visit a secluded sandbar to explore, paddleboard, kayak, snorkel, or sit back grab a drink. Lunch and unlimited draft beer & wine included!

Kids go free!

Clock 2 hours

Sunset Sip & Sail

Grab a tropical mixed drink and dance to a live performance while enjoying a legendary Key West sunset. Includes delicious appetizers!

Clock 1:00PM
Clock 3 hours

Dip & Sip Afternoon Snorkel

Join us for a beautiful afternoon sail out to the reef with a refreshing dip in the crystal clear waters! Jump on Key West’s newest catamaran, The Sandie Cat as we sail to the best reef locations at the 3rd largest living coral reef in the world. This trip includes an open well bar & unlimited draft beer once snorkelers are done in the water.

Here are the 18 best waterfront restaurants in central Palm Beach County

Yes, everything really does taste better by the water. If you live in Florida you know this. If you have just moved to the area, or can't remember the last time you put this piece of wisdom to the test, it's time to experience it.

Whether it's ocean, Intracoastal, lake or river, from north to south, east to west, there is a lot of waterfront in Palm Beach County. Don't be overwhelmed. We'll introduce you to the best waterfront restaurants in the area in tasty geographic bites.

If you live in central Palm Beach County, from the shores of Lake Okeechobee to the Atlantic Ocean, or just happen to be looking for a dining experience with a view that's worth going the extra mile, here they are:

Royal Palm Beach

Asador patagonia restaurant and tiki bar .

The water view: Lake Royal Palm

This casual Argentinian steakhouse and tiki bar located at the corner of Southern and Royal Palm Beach boulevards is focused on creating unique experience with an emphasis on fantastic hospitality. Using the best USDA meats, their menu celebrates the traditional Argentine “asado,” or barbecue grilled meats. The tiki bar behind the restaurant offers a view of the serene lake and a wide selection of libations.

675 Royal Palm Beach Blvd., Royal Palm Beach. 561-651-9477; asadorpatagoniawpb.com

West Palm Beach restaurants

Elisabetta's.

The water view: Intracoastal Waterway

Situated along Flagler Drive just north of Clematis Street in West Palm Beach, Elisabetta's offers fantastic views of the Intracoastal Waterway, multi-million dollar yachts and even the historic Whitehall in Palm Beach. They feature, seafood, steaks, pasta, pizza and an extensive wine list.

185 Banyan Blvd., West Palm Beach. 561-342-6699; elisabettas.com/wpb

E.R. Bradley’s Saloon

The water view: Intracoastal Waterway

This open-air restaurant has been a favorite meeting spot for locals for decades. A local landmark that made the move from Palm Beach approximately 30 years ago, it has practically become a right of passage and part of West Palm Beach's identity. Taking in the nautical motif, guests can relax with the breeze off the water and live music several nights a week while enjoying ice-cold beverages and an extensive and dependable menu featuring salads, soups, sandwiches, tacos, burgers, large plates and more.

104 S. Clematis St., West Palm Beach. 561-833-3520; erbradleys.com

Lakeside Tiki Bar

The water view: Set overlooking Pine Lake.

Located at the Hilton Palm Beach Airport, this waterfront restaurant has the complete Tony Roma's menu (located within the Hilton) along with a full bar. Set on Pine Lake, which connects to Lake Clarke, Lake Osborne and all the way down to Lake Ida, it has multiple boat slips to accommodate those arriving by watercraft. They are open 11 a.m. to 10 p.m. seven days a week.

150 Australian Ave., West Palm Beach. 561-684-9400; hilton.com

The water view: A quiet canal off the Intracoastal Waterway

This vegan bistro put its name on the map by being one of the first restaurants prepared to cater to the family dog — and it’s actually named for the owner’s dog. Located just off of Dixie Highway on Arlington Road, it is situated on the C-51 canal that separates Lake Worth Beach from West Palm Beach, this cozy eatery has a few tables with a view of the canal. The food is fresh, flavorful and consistent, with innovative menu items and specials that capitalize on what’s in season.

8020 S. Dixie Highway, West Palm Beach. 561-586-2622; darbster.com

Palm Beach restaurants

seafood bar at the breakers.

The water view: Atlantic Ocean

The expansive ocean view combined with the upscale ambience make this a destination worthy of a Palm Beach must-do list. Take in the resplendent resort and enjoy "fresher-than-fresh" seafood for lunch or dinner and actually watch as they prepare it in their glamorous, exhibition-style kitchen.

1 S. County Road, Palm Beach. 888-598-8405; thebreakers.com

The covered terrace at this Italian restaurant offers a wide view of the Atlantic Ocean, and early risers say breakfast is truly the best meal of the day here. Al Fresco serves breakfast a la carte, lunch and dinner daily. Their menu features appetizers, pizzas, pasta dishes and entrées. Dine inside or out, but come hungry.

2345 S. Ocean Blvd. at the Par 3 Golf Course, Palm Beach. 561-273-4130; alfrescopb.com

Seaway at the Four Seasons

Beneath a lush canopy of sea grapes, with the sounds of ocean waves soothing your soul, diners find relaxation nirvana with an icy-cold drink and a meticulously prepared meal. You don’t have to be a resort guest to enjoy a delectable meal with a view.

2800 S. Ocean Blvd., Palm Beach. 561-582-2800; fourseasons.com/palmbeach/dining/restaurants/seaway/

Brandon's at Tideline Ocean Resort & Spa

Brandon’s offers wide ocean views and a seasonal menu. To make the most of the azure water, grab an al fresco table on the oceanfront deck and enjoy their chef-driven breakfast, lunch and dinner delights along with a craft cocktail or two.

2842 S. Ocean Blvd., Palm Beach. 561-934-4054; tidelineresort.com

Acqua Café

The view may be limited, but this restaurant just across the Palm Beach town line is an overlooked treasure. Located in a commercial building wedged between the Tideline resort and Lake Worth Beach, its décor is South Beach-blue and silver. The bar is ultra-modern and the torch-lit screened patio is serene and relaxing. The cuisine is “modern, coastal Italian” with seafood, pasta and grilled meat and fish and a nice selection of wines.

2875 S. Ocean Blvd., Palm Beach. 561-547-0005; acquacafepb.com

Lake Worth Beach restaurants

Beach club at lake worth beach golf club.

Sandwiches and paninis, salads and fish tacos, pulled pork and buffalo chicken wraps — this eatery specializes in filling fare for hungry golfers and a serene setting to unwind after a game. The good news is you don’t have to golf to enjoy your visit. The patio overlooks a golf course water hazard with a view of the Intracoastal in the distance.

1 Seventh Ave. N., Lake Worth Beach. 561-582-9713; lakeworthbeachgolfclub.com/the-beach-club

Benny’s on the Beach

The popular dining destination now has two locations at Lake Worth Beach. Benny's on the Beach Pier and Benny's on the Beach Oceanwalk. Since in 1986, Benny's on the Beach Pier location has been serving locals and visitors. Pairing fresh seafood, burgers and sandwiches with mango margaritas and ice cold beer, this hot spot has even pulled in some A-list celebrities like chef Gordon Ramsay and rocker Jon Bon Jovi . Their Oceanwalk location is a mere 100 yards away and opened in late 2022.

10 S. Ocean Blvd., Lake Worth Beach. 561-582-9001; and Benny's on the Beach - Oceanwalk location: 10 S Ocean Blvd Unit 7, Lake Worth Beach bennysonthebeach.com

Lantana restaurants

Dune deck café.

This long-lasting local favorite for waterfront dining overlooks the public beach in Lantana. A super-casual restaurant with an unmatched view serves breakfast, lunch and brunch amid ocean breezes and swaying palms.

100 N. Ocean Blvd., Lantana. 561-582-0472; dunedeckcafe.com

Kona Bay Café

The water view: Sportsman's Park Marina

Sportsman's Park Marina (est. 1962) has an old Florida feel, and Kona Bay Café is a little like stepping back into that past. This breakfast and lunch hot spot even encourages customers to bring their catch from the Lady K drift boat to the restaurant where the staff will cook it for you.

310 E. Ocean Ave., Lantana. 561-429-3606; konabaycafe.com

Old Key Lime House

The Old Key Lime House restaurant is a fixture in Lantana with good reason. From its “fresh catch” menu to its award-winning Key lime pie and sunset water views, the house delivers. The venue also hosts live music from local bands at the tiki bar.

300 E. Ocean Ave., Lantana. 561-582-1889; oldkeylimehouse.com

The Hive Waterfront Restaurant and Tiki Bar

The water view: Lake Osborne

This waterfront restaurant features a family-friendly dock, a full bar and plenty of covered outdoor seating. Situated on Lake Osborne and adjacent to John Prince Park, it is a beautiful respite with tons of birds and wildlife. The food is hearty bar food for hungry boaters, and Hive Hoagies are a specialty with daily lunch specials. The Hive hosts happy hour and music too.

2412 Floral Road, Lantana. 561-513-9168; facebook.com/thehive618

Manalapan restaurants

Breeze ocean kitchen at eau palm beach.

The sound of surf and sea is the backdrop for a fulfilling meal at Breeze. Take in this idyllic setting with good local craft beers, fine wine, refreshing cocktails and a menu featuring sharable plates, salads, tacos, sandwiches and fresh local catches.

100 S. Ocean Blvd., Manalapan. 561-533-6000; eaupalmbeach.com

Polpo at Eau Palm Beach

The water view: Atlantic Ocean

Italian for “octopus,” Polpo brings acclaimed restaurateur Ron Rosa’s seafood-focused menu from the Tri-State area to South Florida. Enjoy upscale fare inspired by regional dishes, an Italian-influenced wine selection, handcrafted cocktails, and classic aperitifs and digestives. Dine inside or outside, within sight of the ocean and terrace firepit.

100 S. Ocean Blvd., Manalapan. 561-540-4923; polpopalmbeach.com

Eddie Ritz is a journalist at The Palm Beach Post , part of the USA TODAY Florida Network. You can reach him at [email protected] . Help support our journalism. Subscribe today.

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Sunset Cruises
Key West Sailboat Sunset Photograph by Edward Johnston
Key West Sunset Cruise
"Serene Sunset Sail" A sailboat enjoys the fabulous Key West sunset
Key West Sailboat Sunset Sail
Sailboat In Key West At Sunset Photograph by Christopher Purcell

COMMENTS

Key West Sunset Cruises & Sunset Sails
202 Williams Street Key West FL 33040. 3055874488 Email Website. Sit back, relax and toast the sunset on your own private charter on the "High Tide" or step back in time aboard the historic schooner "When And If" built for General George Patton to sail around the world in 1939. Allow us make your ideal sail come true!
Sunset Sail Key West
Welcome to Sunset Sail Key West, Key West's most versatile custom charter experience. With three beautiful vintage boats, great local captains and crew, and the pristine waters of the Florida Keys at our disposal, we're confident that we'll have everything you need to make your dream sail come true. (305) 587-4488.
THE TOP 10 Key West Sunset Cruises (UPDATED 2024)
Key West Small-Group Sunset Sail with Wine. 992. Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers.
Key West Sunset Cruise
KEY WEST SUNSET SAIL with LIVE MUSIC. Come sail along on an ocean breeze and enjoy some of Key West's best musicians performing live to the backdrop of the setting sun. You'll eat, drink and party the night away on Key West's original live music sunset sail. So, grab someone's hand and let the music move you as we chase down the world ...
Key West Sunset Sail, Sunset Cruise & Romantic Boat Ride
Key West Sunset Sail on Schooner America 2.0. Enjoy the best sunset sail in Key West on the Schooner America 2.0! Take in the vibrant colors of Key West's famous sunset as you sip complimentary champagne. On this Key West Sunset Cruise, you will magically glide through the crystal clear surrounding waters whilst being taken care of by our ...
Schooner America 2.0: A premium sailing experience in Key West
Call to order 305-293-7245. Schooner America 2.0 sailing offers our most premium sailing experience in Key West Florida. America 2.0 is the newest, largest, most elegant yacht designed for Classic Harbor Line. Added to the fleet in 2011, America 2.0 offers the most exceptional Key West day sailing and sunset sailing one can find.
Key West Sunset Catamaran Cocktail Cruise
Legendary Sunset Sail, Open Well Bar & Delicious Appetizers. Clock. START TIME & DURATION: Departs 6:00pm check-in 5:30pm; 2 hour trip (*seasonal time changes) Map Marker. DEPARTURE LOCATION: 201 William St Key West, FL 33040. Star Outline.
Key West Sunset Cruise, Sunset Sail, Day Sailing & Private Yacht Charters
A 2 hour sailboat ride is a great way to take advantage of your time in Key West to enjoy all of these things. Whether buying tickets for one of our Champagne Sunset Sails, Afternoon Key West day sail, Full Moon, Star-Gazer Sails; or Privately Chartering the schooners for a special family event or corporate event, you will be amazed by America ...
Schooner Champagne Sunset Sail
The perfect Key West sunset sail. Picture yourself on the deck of a romantic 2-masted schooner. Wind blowing in your hair, the tall ship sails into the sunset past the southernmost point of the U.S.A. Sunset aboard the Appledore Star is intended for couples and couples traveling together.
Private Charters
Take in the sunset without the crowds with a private charter at Sunset Sail Key West. Choose from one of our unique classic boats and enjoy the sunset in style as you glide through the aqua blue waters of the keys with your friends and family, or on a romantic trip for two. (305) 587-4488. Book Now.
OUR Key West Sunset Sail Cruise
Listen to the wind fill the sails as we glide through the water propelled by the breeze. Hear captivating stories from Captain Ricky and the crew about the islands as you sail past points of interest. Soak up the breathtaking views of a Key West sunset and enjoy the magnificent afterglow of twilight as we cruise back to port. Book Now. One of ...
About Us
Captain Seth spent years sailing professionally throughout the eastern seaboard and Caribbean, across the Atlantic to the coast of Italy, and even through the Panama Canal. In 2010, after purchasing Conch West on a whim and restoring her for a year, he registered her as a charter boat, and Sunset Sail Key West was born.
Key West Sunset Sail
Join us on the Argo Navis, the only luxury sailing catamaran yacht in Key West, for 2 hours of delicious food, drink, and pleasantries as the sun dips into the water where the Atlantic Ocean meets the Gulf of Mexico. As we sail, you will be enchanted by the changing tropical colors of the sky and soothed by the sounds of the water.
The Best Key West Sunset Cruises (w/Prices & Reviews)
A Key West sunset cruise is a vacation must-do that adds an unforgettable experience to any Key West visit. Choose a graceful sailing schooner, a sleek modern catamaran, or a roomy dinner cruise liner with live music and all the trimmings - this curated selection of the best Key West sunset cruises offers good times set against one of nature's grandest spectacles.
The 8 Best Sunset Cruises in Key West (2024)
5. Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres. 4.5 Stars (2229 Reviews) One of the top-rated and best sunset cruises in Key West is the Key West Sunset Sail with Full Bar and Live Music. Set sail in the late afternoon and enjoy terrific live music, a full open bar, and plenty of delicious hors d'oeuvres.
Key West Sunset Sail Aboard Schooner America 2.0
Overview. Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated ...
Key West Sailing Adventure and Sunset Sails
A top Key West attraction is the Jolly II Rovers famous "Red Sails in the Sunset" 2 hour sunset sail! Take in a memorable sail of Key West's most famous sights while the sun works its magic turning the sky brilliant colors. With our distinctive red sails and being the only square rigged tall ship in Key West, the Jolly II Rover is the ...
Key West Sunset Sails
There's a Key West Sunset Sail for everyone. Sebago offers several styles of sunset cruises for families, friends, or romance on catamarans and schooners. Book 7+ days in advance and receive an additional 5% off your online booking. Enter promo code EARLY at checkout. 305-294-5687. 305-294-5687. Book Now! Home; Tours. All Tours;
Key West Sailing Charters with Argo Navis
Argo Navis is a 75 ft luxury catamaran — the last commercial sailing vessel built in Key West, Florida. We sail year-round from the Key West Historic Seaport offering Sunset Cruises, Brunch Sails, and Day Trips as well as Special Events. All ticketed trips are inclusive of craft beers & cocktails, fine wines, as well as light bites & heavier ...
Danger Charters
Offering luxury sailing charters in Key West for 30+ years. Sunset cruises, snorkeling, kayaking & private charters. See the real Keys - book a tour today! Skip to Content (305) 304-7999. ... Sail into the world-famous Key West sunset on a historic, shallow-draft schooner! This tour is equal parts romance and fun, complete with fine wine and ...
Key West Award Winning Schooner Sailing Cruises
Choose from our award winning Key West Sunset Sail, Key West Windjammer Day Sail, Key West Eco-Tour or start your vacation with our Key West Bloody Mary Sail. Learn More. Discover These Great Key West Wooden Schooners. Step aboard the Appledore II for a true sailing adventure. This two-masted hand-built wooden schooner calls both Camden, Maine ...
The Best Florida Keys Sunset Cruises
O ne of the top things to do in Key West or on a Florida Keys Road Trip is to go on a Florida Keys sunset cruise. Being out on the water in the Keys is a must do and a sunset cruise is an awesome ...
Key West Wind & Wine Sunset Sail 2024 ~ Tours of Key West
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Tours of Key West three years running. Highlights. Rated #1 on Tours of Key West for three years running Beautiful sailing boat; Exclusive Trip with just over twenty passengers; Amazing Key West sunset views; Attentive and Friendly Crew
Schooner When & If
After a summer in Hyannis, MA and a winter in Key West, FL When And If spent the Summer of 2016 touring the Great Lakes for the Tall Ships Festival there before found her new Summer home the following year in Salem, MA. During this time the opportunity arose for Seth to buy the boat and in 2017 he became owner/operator of his treasured vessel.
Top 3 things to do for your bachelorette party in Key West in 2024
Discover the top 3 bachelorette party experiences in Key West for 2024 with Sunset Watersports. Private charters, sandbars, sunset booze cruises, reef exploration! ... Kick off your evening in paradise with a sunset booze cruise like no other. Set sail as the sky erupts in a kaleidoscope of colors, accompanied by live music and an open bar ...
Key Largo to Key West: The Ultimate Florida Keys Road Trip
Key Largo. Mile marker: 108-90 The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo.
West Palm Beach to Manalapan, these waterfront restaurants are tops
The Old Key Lime House restaurant is a fixture in Lantana with good reason. From its "fresh catch" menu to its award-winning Key lime pie and sunset water views, the house delivers.

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Key West’s Original Live Music Sunset Sail

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Chef’s seasonal selection of appetizers are subject to change

BOAT FEATURES

COMMOTION ON THE OCEAN KEY WEST SUNSET SAIL with LIVE MUSIC

Historic Seaport

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Founding member of NOAA Dolphin Smart Program

Eco Tour • Backcountry Snorkel • Sunset (Available Seasonally)

Snorkel 2 Reef Locations • Sunset (Available Seasonally)

Visit Two Living Coral Reef Locations

Remote Sanctuary Reserved For Locals

Taking Visitors To Key West’s Reefs For Over 70 Years

Eco Tour • Snorkel • Kayak • Paddleboard • Sunset Combo Option

Brand New SeaDoo Jet Skis

Tandem + Triple Rides Largest Parasailing Fleet in Key West

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Start Your Day Aboard Key West’s Most Spacious Catamaran

Tranquil Ocean Setting

Key West's Largest & Only State Certified Ocean Waterpark

Afternoon Adventure Aboard Key West’s Most Spacious Catamaran

Reef Adventure by Day, Sunset Magic by Night

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The 8 Best Sunset Cruises in Key West (2024)

Top Pick: Key West Sunset Cruise

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1. Key West Sunset Champagne Catamaran Cruise

2. Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

3. Key West Premium Sunset Sail aboard Schooner with Hors D’oeuvres and Full Bar

4. Key West Sunset Cruise with Tropical Buffet Dinner

5. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres

6. 2-Hour Private Sunset Cruise around Key West

7. Key West Sunset Snorkel with Unlimited Draft Beer & Wine

8. Sunset Tiki Boat Tour in Key West

A Key West Sunset Cruise You Won’t Forget

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