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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Jul 18 - Jul 24
Rum-Runner-Downtown-and-Island-Tour

Rum Runner Downtown & Island Tour

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4 Hrs.
Enjoy this Rum Runner Downtown & Island Tour and get out on the water for some fun in the sun. Cruise the gorgeous water on the best value bar boat in Key West and give a cheer for every gorgeous sight you see. 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 and/or sample rum on board. So, don't miss the boat! Book this experience today!
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Private-Chill-Out-Lily-Pad-Sail-with-Sunset-Sail-Key-West

Private 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.
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Key-West-Pontoon-Sunset-Cruise

Key West Pontoon Sunset Cruise

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2.5 Hrs.
Embark on a captivating Key West Pontoon Sunset Cruise and witness the enchanting magic of Key West's renowned sunsets. Delight in the picture-perfect views as the sun gracefully descends, painting the sky with vibrant hues of orange, pink, and purple. This unforgettable journey promises to be a quintessential Key West experience, offering an idyllic and romantic perspective of the island's natural wonders. Let the Sunset Key West Boat Adventure transport you to a world of tranquility and awe-inspiring beauty. Book yours today!
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4-Hour-Private-Sandbar-Cruise-on-a-Tiki-Bar-Boat

4 Hour Private Sandbar Cruise on a Tiki Bar Boat

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4 Hrs.
Climb aboard a floating tiki bar boat for a truly unique Key West sandbar experience. Enjoy a seat at the bar as you journey the sparkling turquoise water on your way to the backcountry sandbars. Enjoy swimming and fun in the tropical sun at local hotspots as you float the day away. This custom 20 foot tiki bar catamaran features a private bathroom, Bluetooth stereo, and flatscreen tv. Don't miss the boat, book your 4 Hour Private Sandbar Cruise on a Tiki Bar Boat today!
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Rum-Runner-Bar-Boat-Sunset-Cruise

Rum 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. So, don't miss the boat! Book your Rum Runner Bar Boat Sunset Cruise today!
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Private-Key-West-Dolphin-Sightseeing-Charter

Private Key West Dolphin Sightseeing Charter

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4 Hrs.
Set out on an adventure with this Key West Dolphin Sightseeing Charter for up to 6 guests. Enjoy cruising on some truly gorgeous water, within federally protected wildlife sanctuaries, as you scan the horizon for leaping dolphin pods. Curious and playful, dolphins will often come right up to the boat to explore. So hold onto your hats as your captain takes you in search of the bottlenose dolphin and maybe even see some other exciting sea creatures. Book NOW!
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Private-Sandbar-Experience

Private Sandbar Experience

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2 - 4 Hrs.
There's no better way to spend your day than with this Private Sandbar Experience. Travel the crystal clear water of Key West with family and friends to the backcountry sandbars. Feel the sun and the salty breeze on your skin. Take in the moment and admire the natural beauty this part of Florida has to offer. Your captain knows the best spots to make your experience one to remember. Once at the sandbar, get out in the water to splash and play! Swim, relax on floats, or dive down under the water and snorkel. Make lifelong memories, book this experience now!
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Key-West-Sandbar-Snorkeling-and-Island-Hopping

Private Key West Sandbar & Snorkeling Charter

9 ratings
4 Hrs.
Experience the beautiful Florida Keys and its lush mangroves, islands, turquoise waters, and marine life on this Private Key West Sandbar & Snorkeling Charter for up to 6 guests. Skip the usual trips with salty sailors and opt for a day with the nicest captain around. Cruise on a center console and snorkel and chill on a sandbar or opt for some island hopping fun, your trip is totally customizable. Don't miss out, book yours now!
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Rum-Runner-Bar-Boat-Castaway-Cruise

Rum 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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Rum-Runner-Sunset-Downtown-Tour

Rum 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. So, don't miss the boat! Book your Rum Runner Sunset Downtown Tour now!
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2-Hour-Private-Tiki-Boat-Party

2 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 2 hour Tiki Boat Party today!
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Rum-Runner-Bar-Boat-Early-Bird-Cruise

Rum Runner Bar Boat Early Bird Cruise

1 rating
1.5 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!
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Rum-Runner-Downtown-Morning-Cruise

Rum 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!
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Java-Cat-Sail-Kayak-and-Snorkel-Half-Day-Eco-Tour-with-Key-West-Eco-Tours

Java 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 Half Day 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!
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Private-Snorkel-and-sunset-Sail-with-Sunset-Sail-Key-West

Private 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.
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2-Hour-Private-Tiki-Boat-Eco-Tour

2 Hour Private Tiki Boat Eco Tour

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2 Hrs.
Start your morning off right with this 2 Hour 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! Don't miss this experience!
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4-Hour-24-Foot-Sailfish-Charter

4 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!
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Private-Tritoon-Charter-on-the-Barefoot-One

Private 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 sets 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 today!
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Private-Harbor-Day-Sail-Aboard-the-High-Tide

Private 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!
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6-Hour-24-Foot-Sailfish-Charter

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