Key West Private Charters
Enjoy a life of luxury with a Key West private charter. An all-inclusive VIP grade experience, bring your entire crew out for a special occasion on the water. Your professional captain and crew will accomodate your desires and needs, from drinks to itinerary, water equipment and more. Your ticket covers admission for you and your entire party.
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Oct 3 - Oct 9
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Private Trip
Swim Friendly
Restroom
Captain Included
1-6 passenger
Half Day Trip (if duration 3-6 hour)
All Day Trip (if duration 7-12 hour)
Kid Friendly
Pet Friendly
Morning Departure (5am-11:59am)
Afternoon Departure (12pm-4:49pm)
Evening Departure (4:49-11:59pm)
Key West Sandbar Boat Charter
1 rating
4 - 8 Hrs.
Hit the water around tropical Key West with this carefree Barebones Sandbar Boat Charter. Experience the sights and sounds of a beautiful area as you enjoy ample and comfortable seating, expert navigation, and so much more! The sky's the limit with this boat rental unlike any other, but be sure to book early so you don't miss out!
Read morePrivate Snorkel and Sunset Sail Excursion
1 rating
4 Hrs.
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across the water in classic sailboat before jumping in magical blue waters to snorkel and explore the underwater ecosystems off the coast of Key West. Then wrap it all up with a world famous Key West sunset. The perfect way to spend time with friends and family, book your private snorkel and sunset sail today.
Read moreRum Runner Bar Boat Sunset Cruise
7 ratings
1.5 Hrs.
Enjoy a sunset cruise on the water on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and give a cheers for every gorgeous sight. Perfect for you and up to 5 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100 year old shipwreck, and more. You can BYOB or grab drinks at the beach bar at a discounted rate, this trip is a perfect way to end your day. Book your sunset cruise today!
Read moreRum Runner Sunset Downtown Tour
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1.5 Hrs.
Enjoy a sunset cruise on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and give a cheer for every gorgeous sight. Perfect for you and up to 15 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100-year-old shipwreck, and more. You can BYOB or grab drinks at the beach bar at a discounted rate, this trip is a perfect way to end your day. Book your Rum Runner Sunset Downtown Tour now!
Read moreRum Runner Bar Boat Early Bird Cruise
1 rating
2 Hrs.
Cruise the gorgeous water on the best value bar boat in Key West and give a cheers for every gorgeous sight. Perfect for you and up to 5 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100 year old shipwreck, and more. You can BYOB or grab drinks at the beach bar before at a discounted rate, so don't miss the boat! Book your Rum Runner Bar Boat Early Bird Cruise today!
Read moreJava Cat Sail, Kayak, & Snorkel Half Day Eco Tour
1 rating
4 Hrs.
Experience the unbridled beauty of the Keys' on this Java-Cat Sail, Kayak and Snorkel Eco Tour in Key West. You'll appreciate this thoughtful and fun adventure, as you retreat from the crowds and escape on a catamaran sailing adventure. Immerse yourself as you snorkel in the tropical water teeming with life and kayak through lush mangrove islands. If you want an all-inclusive, authentic, and immersive Key West experience, then this is the eco tour for you! Book now!
Read moreRum Runner Downtown Morning Cruise
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1 Hr.
Rise, shine, and hop aboard this Rum Runner Downtown Morning Cruise. Relax and start your day the right way as you sightsee, take photos, and search for marine life on this easy going morning cruise. Enjoy a worry free experience with your USCG licensed captain. Listen to stories of yesteryears and learn a little about Key West's colorful history. Don't miss this one, book your Rum Runner Morning adventure today!
Read morePrivate Tritoon Charter on the Barefoot One
1 rating
2 - 8 Hrs.
Hang out like the locals! The shallow, clear backcountry waters of the Florida Keys set it apart from anywhere else in the country. Just a short boat ride will transport you to what feels like a world away! Explore secluded sandbars, shallow reef patches, and tropical wildlife at your own pace during this private charter. Pack up your favorite refreshments and snacks and cruise into Paradise! Book your Private Charter today!
Read morePrivate Harbor Day Sail Aboard the High Tide
2 ratings
1.5 Hrs.
Cruise the scenic waters of America's southernmost city on a private day sail adventure with the professionals at Sunset Sail Key West. From the history of Mallory Square and Fort Zachary Taylor to the natural beauty of Key West's National wildlife preserve, this comprehensive sightseeing cruise is the perfect way to experience picturesque sailing in Key West with your family or friends. Relax with a drink, take in the scenery, or test your hand at sailing the ship! Don't miss the fun, book today!
Read more2 Hour Private Tiki Boat Eco Tour
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2 Hrs.
Start your morning off right with this Tiki Boat Eco Tour in Key West, Florida. Cruise through Key West Harbor and around Pearl Basin, one of the most stunning locations in the Florida Keys, on this 20-foot Custom Beachcat Tiki Boat equipped with an 8-speaker Bluetooth stereo. Explore the gorgeous, clear Florida Keys water and keep an eye out for dolphins, stingrays, sharks, tarpon and so much more! There's nowhere better to enjoy your favorite beverage than on a Tiki boat so book your spot on this incredible morning eco tour today!
Read more4 Hour 24' Sailfish Charter
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4 Hrs.
The Florida Keys are home to North America's only living coral reef, hundreds of Atlantic bottlenose dolphins, and other amazing wildlife. The best way to experience it is by getting out on the water on this Private Charter that is completely customizable to your wants and needs. Choose from snorkeling, fishing, dolphin watching, or chilling at local sandbars. The options are endless while your experienced captain takes you to the best spots in the area. Immerse yourself in Key West's culture, book this experience today!
Read morePrivate Chill Out Lily-Pad Sail - Up to Six Guests
2 ratings
3 Hrs.
Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating lily pad. Enjoy this unique private adventure with family and friends, away from the crowds. Be sure to take in all of Key West's beauty while relaxing and soaking up the sun from the water. Book today and set out on a private sailing adventure.
Read more2 Hour Private Tiki Boat Party
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2 Hrs.
Join a Private Tiki Boat Party in Key West, Florida with your own custom Beachcat Tiki Boat. Glide through the gorgeous, clear Florida Keys water and take in the stunning scenery of the area around you while listening to some of your favorite tunes on an 8-speaker Bluetooth stereo system. Bring your favorite cocktail, a couple of snacks, and your most fun-loving friends for an adventure everyone will remember! Book this Tiki Boat Party today!
Read moreRum Runner Bar Boat Castaway Cruise
9 ratings
4 Hrs.
Enjoy this Rum Runner Bar Boat Castaway Cruise and get out on the water for some fun to last the summer through. Cruise the gorgeous water on the best value bar boat in Key West and give a cheers for every gorgeous sight. Perfect for you and up to 5 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100 year old shipwreck, and more. You can BYOB and/or sample rum on board. So, don't miss the boat! Book your spot today!
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