HAVANA FLEET
PRIVATE LUXURY CHARTERS
sunset cruises, Dry Tortugas adventures, private events, full-day or over-night yacht charters.
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.
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.
OUR FLEET
HAVANA FLEET
OUR GUEST'S FEEDBACK
Havana Fleet is not a one-size-fits-all tour. Every charter is built around your group, your pace, and your reason for getting on the water. Choose the vessel, set the tone, and let the captain and crew handle the details.
EXCELLENT Based on 20 reviews Posted on Google fruity sunsetTrustindex verifies that the original source of the review is Google. Best fun rental yacht in Key WestPosted on Google Glenn GTrustindex verifies that the original source of the review is Google. There were 6 of us that went out to Dry Tortugas NP. Graham was our captain and treated us great. Smooth (as the ocean allowed) trip out. After giving good advice on how to best tour the fort, he waited patiently. Then took us to Loggerhead island for some snorkeling. Just as we arrived back at Key West, he put us in a great spot for the sunset. I highly recommend this service.Posted on Google Danielle BauerTrustindex verifies that the original source of the review is Google. Such a fun experience! Captain Kelly was great & kept the party alive ! Boat was beautiful, took us out to sunset and was beautiful! Can’t recommend enoughPosted on Google ZIGAFPD1Trustindex verifies that the original source of the review is Google. I can't recommend this company enough. Great time, great boat, and great people.Posted on Google Elizabeth VannTrustindex verifies that the original source of the review is Google. The best time with the best captains! 10/10!Posted on Google Ashley FeTrustindex verifies that the original source of the review is Google. I cannot recommend Captain Kelly and his crew enough!!! This is the 2nd time our group booked the Havana Moon and somehow it was even better than the last. Kristen and Courtney were extremely accommodating, providing more than enough food, drinks, and margaritas. The crew was prompt and professional. Once the 2 new people in our group were familiarized with the boat, we popped champagne and found great photo opportunities. On the way to the island, we spotted flying fish, dolphins, and turtles. The Captain keeps the vibe going with his dad jokes and makes sure we partied at our own pace. My husband is a big fisherman and brought his rod, but we didn't even need it! They had extra rods and tons of bait. Once we were close enough to the island, we dove off the side of the boat and swam until Kristen had the smaller boat ready to drive us to shore. They provided floaties, snorkeling gear, towels, a cooler full of seltzers/water, and a walkie talkie so that we could communicate when we needed snacks and refills. We got back to the yacht just in time to watch the sunset.. The most amazing views were locked in for core memories here. Courtney had dinner and drinks waiting and topped the night off with birthday cake and desserts. Once it got dark, the disco lights turned on and we partied all the way back to the dock. If you're thinking of booking, this is your sign. Do it! It was the best day ever! Can't wait to book again for our next birthday banger. Thanks Captain!
HAVANA FLEET
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 HOUR 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.
2.5 HOUR CHARTER

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.
HAVANA FLEET
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.

