Key West Private Charters

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!

Cruise the scenic water 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!

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!

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!

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!

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 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!

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!

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!

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!

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!

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!