Yachting in Key West, FL
Located at Florida's southern tip, Key West captivates with azure seas, vibrant coral reefs, and a relaxed vibe. Experience the island's allure and enjoy luxury yachting in Key West, FL. Perfect for leisurely cruises or thrilling adventures, Key West is ideal for sun-filled coastal experiences. Discover its beauty from the deck of your private yacht.
52' Viking Princess
80' FF Pendleton
75' Luxe Catamaran
Why charter a yacht in key west, fl, traverse hidden treasures with key west luxury yacht charters, boat rental in key west, .css-1uazooj{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;width:100%;outline:2px solid transparent;outline-offset:2px;transition-property:var(--chakra-transition-property-common);transition-duration:var(--chakra-transition-duration-normal);font-size:1rem;-webkit-padding-start:var(--chakra-space-4);padding-inline-start:var(--chakra-space-4);-webkit-padding-end:var(--chakra-space-4);padding-inline-end:var(--chakra-space-4);padding-top:var(--chakra-space-2);padding-bottom:var(--chakra-space-2);padding:10px 16px;}.css-1uazooj:focus-visible,.css-1uazooj[data-focus-visible]{box-shadow:var(--chakra-shadows-outline);}.css-1uazooj:hover,.css-1uazooj[data-hover]{background:var(--chakra-colors-blackalpha-50);}.css-1uazooj[disabled],.css-1uazooj[aria-disabled=true],.css-1uazooj[data-disabled]{opacity:0.4;cursor:not-allowed;} .css-1pkhz46{font-size:var(--chakra-fontsizes-sm);font-weight:600;-webkit-flex:1;-ms-flex:1;flex:1;text-align:left;} how do i book a yacht on yachtlife .css-g5ledl{width:1em;height:1em;display:inline-block;line-height:1em;-webkit-flex-shrink:0;-ms-flex-negative:0;flex-shrink:0;color:currentcolor;vertical-align:middle;font-size:8px;}, when is my payment collected is it refundable.
Once you confirm your reservation, your broker will process your payment.
- If you are booking for a single day and your reservation is confirmed more than 7 days in advance, a deposit of either $1,000 USD or 50% of the total cost of the reservation (whichever is greater) is processed immediately in order to hold the yacht. Once your embarkation date is 7 days away, the remainder of the amount due is processed.
- If you are booking for a single day and your reservation is made 7 days or less in advance, the total price of your reservation is processed immediately.
- If you are booking for a multi-day charter and your reservation is confirmed more than 30 days in advance, a deposit of 50% of the cost of the yacht is processed immediately in order to hold the yacht. Once your embarkation date is 30 days away, the other 50% is collected for the price of the yacht, plus the APA, plus the taxes due.
Terms of refunds are dictated by the Charter Agreement. Generally, once a payment is collected, it is non-refundable. In certain circumstances, as dictated by the Charter Agreement, credits can be provided so you will be able to enjoy your yacht charter at a future date that is convenient for you.
Why is there a 3% credit card convenience charge?
Are my payment details saved on the app, what if your servers get hacked is my payment information really safe.
305-900-7263
HAVANA FLEET
Luxury charters, charter your dream yacht and experience the adventure of a lifetime.
Havana Fleet Key West Luxury Yacht Charters offers guests an unforgettable experience aboard our fleet of luxury charter boats. Our experienced Captain and Crew will treat you and up to eleven guests like true celebrities, ensuring that you have a once-in-a-lifetime experience. At Havana Fleet, no two trips are alike and every charter can be custom-tailored to your needs & specifications. Custom charter options are endless, so whether you want a relaxing 2 1/2-hour Sunset Cruise or a multi-day adventure 90 miles into the Gulf of Mexico, we have you covered. From your secluded anchorage, you can enjoy stunning sunsets and star-lit skies. Plus, with access to world-class snorkeling and beaches on Loggerhead Key, you can explore at your leisure. Water toys, sport fishing, and personal chef options are also available for your enjoyment. Learn more about our fleet of boats and our luxury charters below.
CHARTER ACTIVITES
Book your adventure.
The Havana Fleet offers a wide selection of activities for everyone. Some of the most popular are snorkeling, fishing, island adventures, sandbar excursions, and sunset cruises. Contact us to plan your luxury charter today.
PRICING & INFO
Havana Fleet offers a wide variety of charter options. We have three different luxury charter boats that offer private luxury charters starting at the price listed below.
2.5 HR CHARTER
Elegant Sunset or Morning Cruises onboard our 36′ Hinckley Picnic Boat, Dolphin Watching, 2 1/2, 4, 6, and 8-hour Custom Island Tour Packages which can include catered onboard or beach picnics. Water toys are available.
2.5 HOUR CHARTER
Your custom charter options are endless! From a relaxing 2 1/2 hour Sunset Cruise 4,6 or 8 hour Island excursion up to a Multi-day and Night adventure 90 miles into the Gulf of Mexico. Explore Fort Jefferson and experience the world-class snorkeling and beaches of Loggerhead Key at your leisure.
Sunset & Brunch 2.5Hr Cruises are available. Dry Tortugas day trips. Tour Fort Jefferson and snorkel Loggerhead Key. 4, 6, and 8-hour and Multi-day High-end Fishing Charters. Thrilling Sunset Cruises. Express Island Tours and Adventures. Water toys are available.
PRIVATE CHARTERS
Experience the ultimate adventure with Havana Fleet in Key West, Florida. Our luxury charter boats cater to your desires, offering custom trips with tailored destinations and activities for groups of up to 12 people. From half-day to multi-day charters, every detail is addressed by our attentive captain and crew. Explore Fort Jefferson & The Dry Tortugas on our exclusive day trips. Let's plan the charter of your dreams with Havana Fleet today!
3 vessels to choose from
Our fleet of luxury charter yachts offers something for everyone. With options for a group of up to 6 or up to 12 guests on our private luxury charters.
Amazing Destinations
Our fleet offers the chance to experience remote destinations like the Dry Tortugas. Experience untouched locations just for the day or on a multi-day excursion aboard our luxury yacht.
Professional Crew
Our dedicated captains and crew are first and foremost committed to the safety of you and your guests while ensuring an unforgettable experience.
Multi Day Trips
Our fleet offers guests the chance to stay aboard and really get a feel for the yacht life. Our crew can plan an amazing itinerary for your guests. Chefs and catering are available to suit your needs.
2.5 HOUr CHARTER
Looking for adventure but don’t have all day? A 2 1/2 Hour Charter will get you on the water and offer enough time to explore some of the local sights or take in a sunset. Activities include island adventures, or sunset cruises.
4 HOUR CHARTER
Spend an afternoon or morning exploring the uninhabited offshore islands and sandbars. Have time to relax on the water and experience more. Activities include island adventures, sandbars excursions, and sunset cruises.
6 HOUR CHARTER
Spend the day on the water enjoying everything our fleet has to offer. Create a custom itinerary that includes a number of destinations and activities of your choice like a sunset cruise and our sandbar excursion or other combinations.
8 HOUR CHARTER
Have the whole day to see what is out there. A full-day charter opens the door to many remote destinations. Our charter boats can comfortably accommodate up to 6 guests on a day trip to Fort Jefferson & The Dry Tortugas.
START THE JOURNEY
Plan your trip.
Let's plan a custom Key West Charter together. Use the contact form below to tell us a little more about your trip.
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Bareboat Charter Key West
by "Charter Booker" | Dec 19, 2017 | Yacht Charter
1. Determine when you want to go on a Key West Bareboat Charter
Knowing when you plan to travel helps determine the cruising grounds you should be considering. Prices, availability and particularly weather, can all vary depending on the time of year and can play an important part in choosing a Key West Yacht Bareboat Charter destination.
2. Determine what type of Bareboat Charter in Key West
Is this a family holiday, quiet romantic getaway, a couple’s or singles trip, etc.? This will determine what type of boat and crew would be suitable, and what islands to visit or activities to plan for on a Key West yacht Bareboat Charter
3. Determine where you want to go on your Bareboat Charter Key West
Yacht charters are available around the globe with The Caribbean and Key West being the most popular. After hurricane, Irma and Maria’s devastation in the Caribbean more potential bareboat yacht charter customers are looking to Key West. The Dry Tortugas and Fort Jefferson remains the most popular destination from Key West for a Bareboat Charter. https://www.nps.gov/drto/index.htm
4. Determine your Key West Bareboat Charter budget.
Price plays a part in most people’s yacht charter. Our staff will help you maximize your budget and may in fact help you get more yacht than you thought possible for a Key West Yacht Bareboat Charter.
5. Determine what style of charter fits your Bareboat Charter Key West.
There are 3 types of a boat charter in key west:, – a crewed yacht charter:.
Your yacht comes with a permanent captain and cook. Price includes all meals and often house wines and open bar. Meals are prepared to your taste (to a very high standard) from individual preferences given to the cook before the charter. You choose the day’s activities and the itinerary, on a day to day basis. Yachts tend to be more luxurious and have more ‘toys’ (kayaks, waterskis, A/C, entertainment centers, etc) than a bareboat charter. The cost per person can be close to or less than the cost on a crowded cruise ship. Matching your party to a suitable crew is an important part of our service. Blue Ocean Yacht Charters currently does not offer Crewed Yacht Charters.
– Bareboat Yacht Charter Key West:
Sail the boat yourself. The principal charterer needs to have skippering experience on a yacht close to the size you are chartering. Equipment standards and reliability can vary considerably, even within a company. It is a mistake to choose a boat purely by price and the cheapest boat is not always the best value.
You can also charter through a bareboat company and add a captain (and cook). This is the ideal way to bareboat charter in Key West. Let us help you find a captain that is familiar with the boat and sit back and relax. Most captains will allow experienced sailors to operate the yacht on their own under the supervision of the captain. Typically boat owners will allow a lower deposit if a bareboat charter customer hires a captain that is familiar with the boat.
Now that you’ve decided the boat charter Key West, the fun really begins. There are so many yachts for you to choose from. Which one is right for you? Our staff knows each and every one of them, and once we know your desires for a dream yacht charter, Blue Ocean Yacht Charters will handle Step 6 for you.
6. Research & narrow your Boat Charter Key West choices.
Our staff will make suggestions and help you narrow down your private boat charter choices. We will do this based on your requirements and our personal knowledge of each boat and cruising ground.
7. Interview the prospective crews and recent charterers.
For a crewed charter, we feel the selection of the crew is actually more important than the boat. A good crew can make up for a mediocre boat but the opposite is not true. We maintain relationships with all yachts and closely monitor feedback from our recent charterers, so we are in an excellent position to find the perfect match for you and your guests.
For bareboat charters, the condition of the boat and the back up services provided by the company are very important as well.
8. Once you’ve decided, inspect the current condition of the yacht.
Any boat and /or crew can look good in a brochure or website. Some are immaculate and some are maintenance nightmares. 3 years of bareboat chartering can cause the same wear as 10-15 years of private use, but with a crewed yacht, maintenance is more important than age. We have inspected every boat you are chartering and can describe its current condition in Key West for a bareboat charter.
9. Arrange the other details.
You’ll need hotel reservations, provisioning options, customs and passport requirements, itineraries, airline tickets, etc… We can recommend and/or handle all of this for you and because of our volume discounts, can probably save you money by bundling your airfare with your Key West yacht charter.
10. And finally…step on board.
Put on your sunglasses, take off your sandals, relax, unwind and enjoy on a private boat charter in Key West. You’ll be remembering this vacation for a lifetime. For real peace of mind, let us do it for you. https://blueoceanyachtcharters.com/our-yachts/
Have a fun bareboat charter and be safe.
“Charter Booker!”
(Charter Booker, manages Blue Ocean Yacht Charters in Key West and writes many of the company’s blogs. Having experience both on the water and off the water helping customers experience the best possible yacht charter for many years. Charter Booker carries American Sailing Association certifications and has extensive knowledge of boat safety and regulations. Call 305-923-4152 and ask for “Charter Booker” when booking your next yacht charter with Blue Ocean Yacht Charters in Key West, Florida.)
Private & Shared Sailing Charters
Sunset sail key west.
Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.
Get inspired with our most popular trips!
Private sunset sail.
Chillout Lilypad Sail
Key West Daysail
Sunset Sail on When & If
Privates Charters
Discover your perfect private charter.
Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.
Shared Trips
Come together on a shared charter.
Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.
Three Classic Boats
View our fleet.
We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.
Real. Fun. Sailing.
When And If is back at beautiful Stock Island Marina!
Check Out Our Ship's Store!
Wreckers' Race Season Is Back!
Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.
Friends of SSKW
Legal & safety.
Three heads are better than one…
Three friends met in a coffee shop on a rainy day, quit their boring corporate jobs and moved to a tropical island to live the dream. Well OK, the real story is we didn’t meet until we were already well ensconced in our Island lifestyles, and it might have been more like a tiki bar as it is Key West after all. But we really are three professional friends with perfectly aligned skills, who through a series of fortunate events ended up working together in an industry we’re passionate about. We share that passion with a team of consummate maritime professionals & land-based staff, who together endeavor to deliver a truly fine experience to our clients, and share what a special place the Florida Keys are with the yachting world at large.
Kimber Tracy
Owner, operations & sales.
Kimber was born & raised on Oahu, Hawaii. The daughter of passionate lifelong sailors, Kimber started sailing at age seven, was an avid surfer through her teens, got into scuba diving early on & worked at the Waikiki Aquarium in Dolphin & Monk Seal volunteer research programs for many years. Her first study expedition was to ID humpback whales in Alaska aboard a 65 ft. Ketch, sailing the magnificent inside passage in 1981. She has since sailed aboard every type of vessel imaginable, from a 3 masted schooner through the Seychelles, Dhows off the coast of Kenya and down the Nile, to the historic Swedish tall ship Tre Kronor over the Baltic. A lifelong love of adventure and exploration has driven her to the four corners of the world and both Polar regions, traveling thus far through over 50 countries mostly solo. She enjoyed a career as a successful entrepreneur and corporate executive in the US and Europe before a stint as a consultant for a well-established charter company ignited an interest to enter the yachting industry as a second career. Kimber enjoys the opportunity to combine her endearing love of the ocean, passion for adventure, international experience of five-star hospitality, with a genuine enthusiasm for helping people fulfill their dream of “sailing off into the sunset” in one of the most beautiful sailing grounds in the United States. Her attention to detail and desire to ensure clients have a first-class time aboard is readily apparent from beginning to end of every charter.
Captain Jon Skiffington
Owner, fleet manager.
Following in his family’s maritime footsteps, Jon came into sailing as a bucket list “must do” 16 years ago. He fostered a dream to leave the white snow behind for white sand and pursue a career in the maritime industry. He managed to cram a good deal of experience into ten years of working with boats and adventuring in and around the North East’s waters before striking out aboard his Pearson sailboat Coyote on a grand three-month adventure from Annapolis to Key West. He joined forces with Kimber in 2016 to oversee fleet management for Key West Sailing Academy and the business partnership continued growing from there. He holds a USCG 50-ton master license, is an ASA sailing instructor and brings to bear a broad experience of vessel management, along with all manner of repair & maintenance. Jon has also enjoyed a busy 35-year career as a professional musician, singer, songwriter, music educator, and toured with several acclaimed musicians in North America & Europe. He enjoys discussing the finer points of sailing with guests and when he’s not playing music with several popular Key West bands, you’ll find him sailing Coyote, enjoying another perfect tropical breeze as often as he can.
Partner, Marketing & Sales
Emily is passionate about all things coastal, beached as it were in her summers spent at the Jersey Shore, sailing and cruising with dad, her grandparents, aunts and uncles in Toms River and running around the Raritan Yacht Club in Perth Amboy catching sailing regattas. Sometimes life comes full circle. Armed with a degree in hospitality management, substantial experience in visual communications, marketing and a burning desire to live a tropical coastal lifestyle, she and her fiancé relocated to Key West where she and Kimber first teamed up in 2013. Before joining forces to master the charter industry, she had a successful career here in Key West as an events/hospitality manager & marketing coordinator for an international hotel chain and several notable Key West operations including the Botanical Gardens. In her down time, you’ll find her with her family on their boat at a sandbar, snorkeling the reef, offshore fishing or catching another famous Florida Keys sunset, all the while documenting every moment with photos. With her passion for photography and the island life be prepared to fall in love with the Florida Keys through her eyes and wanting to see it for yourself.
6651 Maloney Ave, Unit 1 Key West, FL 33040
[email protected] 800-650-6940
KEEP IN TOUCH
Destination and charter fleet updates, special offers, and more
Introducing Vivo Per Lei 58 Leopard Catamaran flagship model Learn More
Creating unforgettable journeys on custom designed luxury catamarans learn more, luxury catamaran sailing charters tailored in every way to suit your needs learn more, key west and key largo locations sailing the beautiful florida keys, bahamas and beyond learn more, catamaran sailing charters half day, full day & overnight learn more, welcome to calypso sailing.
Calypso Sailing was established in 1988 in the beautiful Florida Keys. With locations in both Key Largo and Key West we specialize in luxury sailing vacations on a range of Leopard Catamarans, both bareboat and Captained. Our monohull sailing charters can take groups of 6 to 38 on day, sunset and overnight trips whilst not forgetting the iconic African Queen steamboat from the 1951 movie starring Humphrey Bogart and Katharine Hepburn which operates daily in Key Largo.
Our aim is taking care of all your cruising needs
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