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Key West Sailing Charters

Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.

Our Key West Sailing Charter Fleet

Sailing cats.

Southern Cross Catamaran

Southern Cross

Indoses boat

Fountain Pajot Elba 45

dream reach leopard 44

Dream Reach

catamaran charter florida keys

Sugar Magnolia

Honu Kai Catamaran

Seawind 1260

Second sight.

catamaran charter florida keys

Stay Glassy

Nautitech 40 open.

Ever Summer Exterior

Ever Summer

Fountaine pajot my44, key west attractions.

Duval St. in Key West

Historic Duval Street

One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.

Romantic Sunsets

Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!

Key West sunset

Crystal Clear Snorkeling

Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.

Pristine Sandy Beaches

Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.

Key West south beach

Catamaran Echo - Key West

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catamaran charter florida keys

$10 Off each person – Promo Code “EchoDirect”

(for Public trips only – sold by the seat)

catamaran charter florida keys

Catamaran ECHO 2

Current public & private trips – book here online, (free shuttle to the echo 2 dock from the perry hotel).

catamaran charter florida keys

Catamaran ECHO 3

Custom private charters – text 305-304-2633, regularly scheduled public & private trips starting soon, …is a fast and comfortable sailing machine, providing the most stable ride on the water. naturally it’s a catamaran.

And with our big bimini top, you can get all the Key West sun or shade that you want. The fresh water shower on deck comes in handy on those hot days. A private bathroom in the cabin makes a day in the wildlife refuge civilized and helps protect our tropical waters.

ECHO 2 is located at the “Key West Historic Seaport” which is downtown in Old Key West at the famous Key West Bight. The Historic Seaport “Harbor Walk” goes right around the water’s edge and leads right to ECHO’s dock along side the famous “Boat House Restaurant at Turtle Kraals”. Spend the day on the Harbor Walk before and after your ECHO trip and visit all the great shops, restaurants and bars and galleries. This is where all the locals hang out!

So come and hang out in the coolest part of town and cruise with us at Catamaran ECHO ..

catamaran charter florida keys

ECHO'S Official Website

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Wild Dolphin

Snorkeling & Sailing Adventure

Click here to read more!

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Private Day Charters

2 to 19 Passengers

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Sunset Cruise - Adults Only

Private Trips Available (all ages welcome)

Towel (day trips), Sun screen applied (no oil), Hat, Camera, Sunglasses (polarized best), a jacket in fall, winter, spring (even if you think it’s warm out), a small bag to secure your things, a few bucks and a Big Smile!

Echo Upgrades

Please reserve upgrades in advance while reserving here online, or by phone or email before the trip.

Directions, Cruise Ship & K.W. Ferry Passenger Info

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Certificate of Excellence 2019

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Catamaran Echo - Private 2 Hour Champagne Celebration Sunset Sail

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Sail the Florida Keys

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Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

catamaran charter florida keys

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

Browse our yachts for charter in Florida Keys

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The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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Bridging the space between reality & paradise.

catamaran charter florida keys

A luxury sailing catamaran charter with an emphasis on fun and adventure.

Sailing from Ft. Lauderdale, The Keys & The Bahamas.

Come sail with us!

Luxury Catamaran Guest accomodations

Meet The Crew

catamaran charter florida keys

Captain -  Scott Clark

He is most at home when on the water.  He enjoys tinkering with everything, but has a flair for all things electrical. He loves sharing stories, creating videos and spending time with his wife and 2 sons.

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First Mate - Holly Clark

She is most at home when she is spending time with friends and family. She enjoys cooking, meeting new people, yoga and snuggling with her granddog, Pugsly.

catamaran charter florida keys

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SERENITY NOW

Sailing Serenity Now Key west Catamaran

Private Charters Key West Florida

Private crewed sailing packages.

Set sail on your own private catamaran and explore the only living coral reef in the continental United States.  Sail the pristine turquoise waters of the Florida Keys and enjoy a relaxing afternoon on a secluded beach.  As a private charter you, and up to 5 of your guests, have the option to customize your adventure.

Full Day Sail  Adventure

Full Day Sail  Adventure Lunch and Optional Snorkeling

Starting at $1200

Half Day Sailing Adventure with

Optional lunch and snorkeling.

Starting at $600

Sunset Sailing Adventure with  Appetizer  and optional Snorkeling

Sailing catamaran "serenity now".

Up to 6 Passangers max

Sailing Catamaran

S/V "Serenity Now"  is a Fountaine Pajot Lipari 41.  She has a large comfortable trampoline on her bow and a spacious covered cockpit on her stern. Inside you will find a settee with seating for six along with four cabins and two large heads.

About Your Crew

Captain Tom and his wife Denise have been sailing for over two decades.   Over the course of the last three years they have sailed over 4,000 nm along the east coast of US and the Caribbean Sea.  Tom holds a USCG OUPV Captain's License.  Prior to their most recent adventure, Tom was a Research Physicist and his wife a Public Relations Manager.  Bow and Harry our French Hounds server at the pleasure of our guest or vacation at a nearby pet resort during charters.

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6810 Font Street

Key West FL 33040

[email protected]

410-849-9199

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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, catamaran charters in key west, florida.

Enjoy an Adventure in the Florida Keys on this Catamaran

Key West, FL

boating guide

In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:

  • 25 boat rentals in Key West, FL
  • 25 boat rentals in Stock Island, FL
  • 25 boat rentals in Key Haven, FL
  • 25 boat rentals in Cudjoe Key, FL
  • 25 boat rentals in Summerland Key, FL
  • 25 boat rentals in Little Torch Key, FL
  • 25 boat rentals in Big Pine Key, FL
  • 10 boat rentals in Marathon, FL
  • 10 boat rentals in Key Colony Beach, FL
  • 10 boat rentals in Duck Key, FL

Catamaran Charters in Key West, FL | Sailo Boat Rental

Looking for a catamaran charter in Key West? Boat rental in Key West, Florida   is always a great way to enjoy sailing trip experience in Florida. Choose your perfect catamaran charter with Sailo and set a course for adventure! When you rent a boat in Key West, you can choose your own itinerary and explore at your leisure. Want to relax on deck? Prefer to do some fishing? Or maybe you just want to escape the crowds? Find your ideal yacht rental in Key West with Sailo.

Our finest collection of catamaran charters in Key West, FL

Key West, FL is a well-known boating destination in the US, perfect for a memorable experience on a Sailo boat. The catamaran rentals are popular for both locals and tourists and a great choice if you want to spend some quality time with your family or friends. 7 charters are currently available with or without captain, lined up in the Key West’s marinas, waiting for their guests. Rent a private catamaran in Key West with Sailo: it’s easy, quick, secured and the best choice for a fun experience in the waters of Florida.

How to find the ideal catamaran charter in Key West, Florida?

Sailo has the most advanced filters to help you find the perfect boat rental for an amazing experience on the water in Key West, FL. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Florida, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How much does it cost to charter a catamaran in Key West for a day?

Whether you are looking to rent a catamaran yacht in Key West for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Key West is $1100. You can however find excellent affordable rentals from $250 and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Can I pay in installments for my Sailo catamaran rental in Key West?

A lot of our boat owners allow payment in installments, particularly for the weekly charters. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Guidelines to responsible yachting

If you’re looking to explore our beautiful planet, a yacht charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto:  'Take only photos, leave only wake'  (OK, so we paraphrased). To be a responsible sailor, remember:

  • Don’t disturb coral or sealife
  • Take your trash home (and don’t throw anything in the sea)
  • Respect the locals and their customs wherever you go

Read more about responsible boating.

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The Florida Keys

Related Locations

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Featured Yachts in Florida Keys

Luxury Superyacht KENSHO By Admiral Yachts

KENSHO | From EUR€ 850,000/wk

Latest florida keys yachting news.

Horizon Yacht launches 34m motor yacht CROWNED EAGLE – the fifth FD110

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Florida Keys Yacht Charter

Often considered America 's Caribbean Islands the Florida Keys yacht charter offers spectacular locations to explore.

You will often read references to a 'jade necklace' or a 'string of pearls' in descriptions of the many (800+) islands that stretch off into the sea. The Keys have become increasingly busy over the last few years with an increase in cruise ship and other tourism. The keys feature plenty of energy ashore, but to get away into the quieter areas a charter yacht is the only way to go.

catamaran charter florida keys

Photos: 1. A diver explores the coral reef in the Florida Keys National Marine Sanctuary off Key Largo - The reef system in the Keys is the only contiguous coral barrier reef in North America - Photo by Bob Care-Florida Keys News Bureau; 2. A Florida Keys fishing guide positions his angler to cast for a bonefish off Key Largo- Photo by Bob Krist-Florida Keys News Bureau; 3. Sunset in Key Largo- Florida Keys- paints a pretty picture at the Kona Kai Resort -Photo by Bob Krist-Florida Keys News Bureau

The first Key to come across on your cruise south will be Key Largo . Over the years Key Largo has become a busy weekender retreat from the mainland. As you sail further down though the Keys you will finally come to the last one, Key West .

The Florida Keys are sheltered by the only living coral reef in the United States. The Keys are well known to yacht charterers for the spectacular scuba diving and snorkelling, kayaking and eco-tours, dolphin watching, island hoping and fishing.

The types of yacht charter available in the Florida Keys are all the main types including motor, sailing, bareboat charter, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and super yacht charter.

The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races, motor yacht races, Fantasy Fest, a lighted boat parade and Florida's own 10 day long Mardi Gras. We recommend charter yachts with a draft of under 4 or 5 ft (1.3 - 1.5m), as with a catamaran, so that you can get in to all the best areas within the Florida Keys.

Key West Yacht Charter

Key West has the ideal year round climate for yacht charter. Key West is a very unique town being the southernmost US city where history and tradition meets natural beauty and serenity. This city has real estate titles that date back to the King of Spain! Within walking distance from the historic Seaport District you will find palm-lined streets, tropical gardens, Ernest Hemingway's home, fine shops, art galleries, quaint restaurants and cafes. You can walk in the footsteps of Thomas Edison, Lou Gehrig, Harry Truman, and Tennessee Williams. You will also discover lively bars and pubs along with street musicians, jugglers, mimes and artists.

It is not unusual for charter guests to day sail their charter yachts using Key West as a base. They will sail and explore the keys during the day, utilising the restful anchorages, and then return to the first class marinas at night to experience Key West's nighttime entertainment. Remember to radio ahead to reserve marina space, as Key West is a busy part of the Florida Keys.

Below is a selection of fabulous Florida Keys charter yachts - please, contact us for additional vessels and more information here .

  • Florida Keys Charter Itinerary
  • Browse Florida Keys Charter Yachts
  • Luxury Motor Yachts for Charter in Florida Keys
  • Luxury Sailing Yachts for Charter in Florida Keys
  • Luxury Catamarans for Charter in Florida Keys
  • Florida Keys Yacht News

Florida Keys Yacht Charter Enquiry

"I have just emailed your post charter feedback to you. It doesn't say nearly enough about how well and hard you worked on this deal. I am a retired commercial real estate broker who understands the importance of the deal-maker in the deal. You are a deal maker of the first order." E. G - chartered in Florida Keys.

Yachting Destinations Near the Florida Keys

In close proximity to the Florida Keys are a number of exciting sailing destination.

Delta Pacific Northwest

New England

New England Lighthouse In Late Afternoon The Portland Head Light At Portland Maine USA

Napa Valley

Yachts for charter in the florida keys, queen miri | from eur€ 1,125,000/wk.

Exterior

WAYFINDER | From EUR€ 375,000/wk

Yacht Support Vessel WAYFINDER Cruising With Tenders

MARIA | From US$ 230,000/wk

The 52m Yacht MARIA

LADY ELAINE | From US$ 225,000/wk

Exterior - Main

GIGI | From US$ 225,000/wk

The 49m Yacht HARMONY

TCB | From US$ 215,000/wk

Luxury Superyacht TCB

MYSORAH | From US$ 200,000/wk

MYSORAH (ex Major Wager)

ASPEN ALTERNATIVE | From US$ 199,000/wk

Motor Yacht Aspen Alternative

FAM | From US$ 195,000/wk

Forward: Yacht FAM's Cruising Captured

GLORY | From US$ 179,000/wk

Luxury yacht AKULA

ZOOM ZOOM ZOOM | From US$ 175,000/wk

Running

AVALON | From US$ 155,000/wk

Running Shot

FOCUS | From US$ 150,000/wk

Yacht FOCUS - Profile Underway

AQUASITION | From US$ 150,000/wk

Profile Aspect Aboard Yacht BIG ZIP

RELENTLESS | From US$ 150,000/wk

Exterior

PERSISTENCE | From US$ 140,000/wk

Superyacht PERSISTENCE

CLAIRE | From US$ 139,500/wk

Forward Aspect On Yacht CLAIRE

ICE 5 | From US$ 135,000/wk

The 46m Yacht ICE 5

BLUE DEVIL | From US$ 130,000/wk

Motor Yacht BLUE DEVIL

Florida Yacht News

Florida charter yacht REAL SUMMERTIME offering 10% discount

Florida charter yacht REAL SUMMERTIME ...

38m superyacht GLORY offering charters around Florida and the glorious Bahamas

38m superyacht GLORY offering charters ...

Remodelled superyacht PERSISTENCE offered for charter in Florida

Remodelled superyacht PERSISTENCE ...

26m Riva motor yacht GYPSEA ready for winter charters in Florida and the Bahamas

26m Riva motor yacht GYPSEA ready for ...

Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

Sailing Catamaran Sirius

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Sailing Catamaran Sirius - All You Need to Know BEFORE You Go (2024)

catamaran charter florida keys

Florida Keys

Some of the most unique vacation destinations in the world can be found in unexpected places – such as the Florida Keys. Located just off the coast of South Florida, these islands have a relaxed feeling, stunning tropical scenery, and exotic wildlife; yet they are all located a relatively short distance from cosmopolitan Miami and the excitement of South Beach, where the journey begins.

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  • Newfound Harbour

Miami is South Florida’s playground, and for good reason – there is no where like South Beach to both enjoy the sun, sand, and surf by day, and live it up by night in the area’s many exclusive night clubs and restaurants. Whether you want to dance all night and enjoy premium bottle service or simply have a wonderful meal by the water, launching in miami ensures that you will start your voyage off in the most exciting way possible.

Visiting during one of the many major annual events that occur in Miami (including Art Basel, the South Beach Wine & Food Festival, the Orange Bowl, and more) will make your trip even more outstanding.

As the northernmost and largest island in the Florida Keys, Elliot Key was once used a refuge for pirates and today it is home to Biscayne National Park, with its lush vegetation and amazing beaches that offer both remarkable solitude and spectacular vistas – along with a variety of exotic birds and butterflies. You can also explore the island by kayak – there are many hidden lagoons, mangrove-covered shorelines, and winding creeks to discover. What’s more, you can enjoy your own catch for dinner after a day of capturing fish, lobster, or crab.

Key Largo is considered the “Diving Capital of the World”, with plenty of scuba diving, snorkeling, and sport-fishing options for avid enthusiasts – what’s more, it is located near the Everglades, allowing for easy access for kayaking and eco-tourism as well. It is the home of the only living coral barrier reef in the continental United States, and enjoys more than three thousand hours of sunshine per year, making it perhaps the quintessential island vacation destination.

Named after the original settlers’ boat the “Island Home” and now nicknamed the “Village of the Islands”, Islamorada is home to many notable residents (including Major League Baseball players Ted Williams and Miguel Cabera as well as actor Gene Hackman), this is one of the more serene island destinations in the Florida Keys as well as one of the world’s premier fishing destinations. Luxury resorts, shops, and art galleries are part of the Islamorada scene, but there are plenty of beaches that offer more solitude.

With less than two hundred residents, Duck Key is perhaps the closest version of a deserted island that’s still easily accessible from the contiguous U.S.  With world class fishing and sandy beaches, the island is also home to a luxurious spa and offers the opportunity for visitors to swim with dolphins.

Newfound Harbour not only offers spectacular scenery, it is home to the Florida Keys Sanctuary preservation area, which is partially located within the Coupon Bight Aquatic Preserve. The amazing sea life that visitors to the island will enjoy includes star corals and giant brain corals – perfect for amateur or inexperienced divers since these are located within in depths of 18 feet or less. Angelfish, butterflyfish, surgeonfish, damsels, wrasses, grunts, snappers, and parrotfish swim alongside the occasional grouper, along with many other types of fish that you’ll find colorful, striking, and unusual.

Along with some of the most interesting coral reefs in the world, Newfound Harbour is home to a sheltered tropical lagoon that serves as an oasis for a wide range of wildlife, including the tiny Florida Key deer, wading birds, and sea turtles.

Taking a little time to leave it all behind in Key West may be the ultimate form of relaxation – particularly if you happen to visit during one of the island’s most distinctive festivals (The annual Fantasy Fest held in October is the most famous). There’s excellent opportunities for scuba diving and snorkeling around the coral reefs and shipwrecks in the nearby waters, including the recently sunk USNS Gen. Hoyt S. Vandenberg, which created an artificial reef.

However, the island’s unique National Parks and wildlife refuges are perhaps the most interesting (at least for nature buffs), and the nightlife in general is not to be missed, with a variety of options that range from casual tropical dives to trendy nightclubs. All in all, Key West is the perfect culmination to your customized trip through the Florida Keys.

Sailing the Florida Keys may possibly be the very best way to unwind and explore a corner of the United States that hardly resembles anywhere else in the country – or the world, for that matter. And there’s no better way to experience this special part of the world than on your own private yacht.

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Florida Keys Sailing

catamaran charter florida keys

The Spanish first found the Keys during Ponce de Leon's expedition in 1513. They mapped and named the Keys principally as an aid to their ships, which, full of gold and silver, used the Florida Straits to go from the New World back to the Old. The first settlement was at Key West, in 1882, a little more than two decades before Florida became a state. The other Keys pretty much stayed deserted until 1874, when the government surveyed them. After the survey, the government plotted land for businesses and homes. The early homes were primitive. They were built from the local beaches, made of wood and other materials washed up from shipwrecks. In 1912 Henry Flagler built a railroad to Key West. This greatly increased human settlement of the Keys. The railroad was destroyed by a hurricane in 1935, but in 1938 the longest over-water road in the world was built on the railroad's foundation. It includes 42 bridges--one that is seven miles long! This opened the Florida Keys up to a growing tourist trade.

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Bareboat Charter

A bareboat charter means the charterer, as Captain, is solely responsible for the safe operation of the vessel, including all aspects of navigation, anchoring, docking, and controlling the vessel under sail or power. Key West is considered an advanced sailing destination and for the safety of other passengers and the vessel, it is vital the charterer have sufficient experience aboard vessels of a similar size & type as what you are seeking to hire. We also require there be one other person aboard to act as first mate, with enough boating experience to handle the vessel in the event the Captain is injured or goes overboard.

All of our bareboat charters have a 5 day/4 night minimum which is the ideal amount of time to experience one of our Florida Keys sailing itineraries .

Am I qualified?

Sail with confidence, am i qualified for bareboat charter.

The Florida Keys is considered an advanced sailing destination, offering great natural beauty in sometimes rare peaceful isolation. There are almost exclusively anchorages in our cruising grounds subject to tidal changes and currents, including open anchorages in the Westerly Island groups.

Our bareboat charter application will help us evaluate your sailing experience to establish your skill level, and that of your first mate, as suitable to these conditions. This application should be filled out in full, providing as much information as possible to validate your skills and experience. Please submit the requested documents together in order to complete the application process. No booking should be considered confirmed until this application has been approved by the reviewing Charter Base Manager. You may be contacted directly to answer any questions they may have.

Bareboat Charter General Qualifications & Requirements

•30 days or 400 miles in the last three years as named Captain on an equivalent size & type of yacht(s).

•ASA, US Sail, RYA or ICC certification to an equivalent Bareboat Charter level for Monohull & Multi Hull for Catamaran.

•Physically capable of handling the vessel in all situations & conditions (i.e. Managing sails, lines & anchor).

•Must have a qualified First Mate who completes a Crew Resume for approval.

•Must present a valid US driver’s license, or International Passport to verify identity and DOB.

•We reserve the right to approve your application on the condition of having a Check-Out Captain aboard for the first day (or more) at your expense, which would be agreed to in advance as a condition of approval.

•For applicants under the age of 30 or over 74 additional crew requirements may apply.

Don’t be discouraged if your experience isn’t quite strong enough yet. We offer several ways to assist charterers to meet the requirements. As well as being able to offer an ASA instructor accompany you on your bareboat charter so you can achieve your ASA Sailing Certifications , we can also arrange a one or two day refresher for an experienced mariner that might need to get familiar with some of the more advanced systems on newer boats, or just brush up on skills if it’s been awhile. These programs are very flexible and can be personalized to each charter guest.

Download our Captains Application: Captains Application for Sailing Vessels

First Mate’s Application for Sailing Vessels

For Power Vessels

During the charter check-in process, which takes approximately 2½ hours, you will receive a very comprehensive yacht systems orientation, inventory review, safety briefing, and a chart briefing of the cruising area to ensure you are comfortable with your float plan and the vessel. It is required that the Captain & First Mate arrive at the same time and attend the vessel check -in.

Optional Orientation cruise If you are chartering a manufacturer of boat for the first time and would like to do a short orientation sail to familiarize yourself with all the systems and equipment while under way, we highly recommend an orientation sail with a Captain familiar with your sailing vessel. It takes about an hour and they charge $150.00. This is an excellent way to do a shake down sail to make sure you can enjoy your vessel with confidence. This must be booked in advance to ensure there is a Captain available. This is not intended to teach boat handling skills.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

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catamaran charter florida keys

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  1. Sailing The Space Between Promo: Catamaran Charter in S Florida, Keys

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  2. Power Sail Catamarans in Florida Keys-All Inclusive Charter

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  3. Sailing Catamaran Charter in Florida Keys

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  4. Charter 42ft "Tortuga" Sailing Catamaran in Key West, Florida

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  5. Life On A Catamaran in the Florida Keys

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  6. Charter 42ft "Tortuga" Sailing Catamaran in Key West, Florida

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  1. EDELCAT 33 ELLIOT KEY

  2. Exploring Deep In The Bush

  3. Let’s Go Back To Florida!

  4. EP 5

  5. ☀️ Sandbar Party

  6. ConchTV Florida Keys and Key West

COMMENTS

  1. Florida Keys Catamaran Yacht Charter

    Browse a unique selection of Florida Keys Catamaran Yacht Charter and embark on the most exclusive luxury retreat. The tranquillity of cruising, coupled with the warm crew's services, gourmet cuisine, and tailored itineraries, encapsulates the essence of opulence that Florida Keys is renowned for, creating unforgettable memories on the gentle Florida Keys tides.

  2. Key West Sailing Charters

    Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas.

  3. Calypso Sailing

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  4. Florida Keys Yacht Charters & Sailing Vacations

    The Florida Keys possess everything necessary to have a dream vacation. Please note: This base is seasonally closed September 7 - 21. This base is also closed July 4th, November 25th, and December 25th. You must be qualified to sail in this destination. Please submit a Captain's Resume and a First Mate Resume before booking this destination.

  5. Private Catamaran Sailing Charters Key West Florida

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  6. Catamaran Sailing Vacations in Florida

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  7. Sailing Charters in Key Largo and Florida Keys

    Calypso Sailing offers three catamarans and bareboats for charter in the Florida Keys and Caribbean Islands. Learn about the bareboating procedure, the vessels, the itineraries, the safety equipment and the provisioning service.

  8. Florida Keys Bareboat & Crewed Yacht Charters

    Explore the Florida Keys by sailboat with Sail Connections, a leading yacht charter operator with a range of bareboat and crewed options. Find your ideal catamaran, monohull or motor boat for your vacation and enjoy the natural beauty and attractions of the Keys.

  9. Sailing Catamarans for Charter in Key West

    Explore our curated fleet of sailing catamarans available for bareboat charter, captain charter and ASA sailing instruction. ... The Florida Keys. Miami, Bahamas & Florida West Coast. Learn to Sail; Yacht Management; Request Quote; Sailing Catamarans TODscott 2023-03-07T12:48:18-05:00.

  10. Lady Susan Catamaran

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  11. Crewed Sailing Catamaran Charter

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  12. Key West Private Charters

    Private Crewed Sailing Packages. Set sail on your own private catamaran and explore the only living coral reef in the continental United States. Sail the pristine turquoise waters of the Florida Keys and enjoy a relaxing afternoon on a secluded beach. As a private charter you, and up to 5 of your guests, have the option to customize your adventure.

  13. Florida Yacht Charters & Sailing Vacations

    When you set sail on a Florida yacht charter with The Moorings, the cost of your vacation will be based on several factors, such as: The duration of your relaxing vacation; When you book your Florida yacht charter for - peak sailing season months may cost more; Whether you book one of our world-class catamarans, monohulls or power yachts

  14. Catamaran Charter in Key West, FL

    Whether you are looking to rent a catamaran yacht in Key West for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you'll find the best one for you on Sailo. The average starting price to charter a yacht in Key West is $1100. You can however find excellent affordable ...

  15. Florida Bareboat & Captain Yacht Charters

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  16. Florida Keys Yacht Charter Boat Rental

    The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races, motor yacht races, Fantasy Fest, a lighted boat parade and Florida's own 10 day long Mardi Gras. We recommend charter yachts with a draft of under 4 or 5 ft (1.3 - 1.5m), as with a catamaran, so that you can get in to all ...

  17. Sailing Catamaran Sirius

    266 reviews. #10 of 117 Boat Tours & Water Sports in Marathon. Boat Tours. Write a review. See all photos. About. Experience exciting sailing with fresh breezes on our signature Sunset Sail aboard the sailing catamaran "Sirius". Private charters available: Weddings, Celebration of Life, Business Groups, etc. Marathon, Florida.

  18. Florida Keys Luxury Yacht Charter

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    Captain Charter. Sit back and relax on your own private yacht while a professional takes the helm to show you the best of the Florida Keys. We offer multi-night yacht charter vacations. All of our Captain Charters have a minimum of 5 days/4nights which is the ideal amount of time to experience one of our Florida Keys sailing itineraries.

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  21. Florida Keys Sailing Charters

    This greatly increased human settlement of the Keys. The railroad was destroyed by a hurricane in 1935, but in 1938 the longest over-water road in the world was built on the railroad's foundation. It includes 42 bridges--one that is seven miles long! This opened the Florida Keys up to a growing tourist trade. Book Now

  22. Sail and Power Catamarans in Florida Keys

    Fantastic Italian power catamaran with incredible range (over 1200nm) very low fuel consumption and very shallow draft , great for Bahamas term charters. Magic star is located in Miami and can travel to the Florida Keys or the Bahamas. She accommodates 8 guests in two king cabins, 1 aueen and 1 twin size cabins.

  23. Key West Bareboat Charters

    Bareboat Charter General Qualifications & Requirements. •30 days or 400 miles in the last three years as named Captain on an equivalent size & type of yacht (s). •ASA, US Sail, RYA or ICC certification to an equivalent Bareboat Charter level for Monohull & Multi Hull for Catamaran. •Physically capable of handling the vessel in all ...

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