Key West Private Charters

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!

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!

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!

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!

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!

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!

Embark on an unforgettable 6-Hour Private Boat Charter in Key West, Florida. Tailor your day to suit your interests as you choose from an array of exciting activities. Indulge in the ultimate relaxation at a remote sandbar, dive into the crystal-clear water for snorkeling, paddle along serene mangroves on a kayak, try your hand at paddleboarding, or even partake in some near-shore fishing. Immerse yourself in the natural wonders of the ocean, encountering sea turtles, tropical fish, dolphins, vibrant coral reefs, and more! Escape the crowds as you cruise off the beaten path, creating memories to last a lifetime with your family and friends. Do not miss out and book your private charter today. Your personalized adventure awaits!

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!

Climb aboard for a day of ultimate relaxation on this Private Key West Morning Boat Charter. Get ready to cruise away on a day to remember where you can do it all. Choose from any or all activities including snorkeling, kayaking, paddleboarding, guided ecotours, sandbar trips, family fishing, or just cruising and sightseeing. Totally private and customizable! It’s your day and it can be designed around you and your interests. With no set schedule to adhere to, you may spend as much time doing each activity as you like, just let your Captain know and he will try to make it happen.

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!

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!

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!

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.

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!

Embark on an unforgettable Private Sunset Boat Charter in Key West, Florida. As you wait for the sun to set indulge in the ultimate relaxation at a remote sandbar, dive into the crystal-clear water for snorkeling, paddle along serene mangroves on a kayak, try your hand at paddleboarding, or even partake in some nearshore fishing. Witness the sky erupt in a stunning array of colors as the sun sets beyond the Key West horizon. Do not miss out and book your private sunset boat charter today.

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!

Embark on an unforgettable 4-Hour Private Boat Charter in Key West, Florida. Tailor your day to suit your interests as you choose from an array of exciting activities. Indulge in the ultimate relaxation at a remote sandbar, dive into the crystal-clear water for snorkeling, paddle along serene mangroves on a kayak, try your hand at paddleboarding, or even partake in some near-shore fishing. Immerse yourself in the natural wonders of the ocean, encountering sea turtles, tropical fish, dolphins, vibrant coral reefs, and more! Escape the crowds as you cruise off the beaten path, creating memories to last a lifetime with your family and friends. Do not miss out and book your private charter today. Your personalized adventure awaits!

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!

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.