- Most Popular Jet Ski Tour
- Casa Marina Location Casa Marina
- 1 to 2 people Occupancy 1 to 2 people
- 90 Minute Duration 90 Minute
Circle the island of Key West in 90 minutes and experience a unique perspective of the Gulf of Mexico and the Atlantic!
All Key West Tours & Rentals
Cruise Around Key West!
Barefoot Billy’s has been delighting visitors to Key West for over 25 years. While Barefoot Billy’s is world famous for our Island Jet Ski Tour, we offer so much more! Explore the water on a paddle board, take to the land with a fun scooter rental, or leave the navigating to us as you sit back and relax on a Key West boat cruise. Choose your adventure below.
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- Most Popular Cruise
- Garrison Bight Marina Location Garrison Bight Marina
- All ages Ages All ages
- Up To 38 People Occupancy Up To 38 People
- 2 hours Duration 2 hours
Take in a breathtaking Key West sunset on this harbor cruise that sails past the southernmost point of the U.S. and cruises by a Civil War Fort.
- Most Popular Rental
- Casa Marina Location Casa Marina
- 1 person Occupancy 1 person
- 4 hours, multiple days Duration 4 hours, multiple days
Cruise around the streets of Key West and discover the island like a local with this fun single rider scooter rental!
- Kid Friendly!
- Garrison Bight Marina Location Garrison Bight Marina
- All ages Ages All ages
- Up to 36 people Occupancy Up to 36 people
- 3.5 hours Duration 3.5 hours
Search for wild dolphins in their natural habitat and snorkel Key West’s backcountry waters off the Seabreeze!
- Our Newest Boat
- Garrison Bight Marina Location Garrison Bight Marina
- All ages Ages All ages
- 1-6 People Occupancy 1-6 People
- 2 to 8 hours Duration 2 to 8 hours
Create the perfect outing for up to 6 with a custom charter! Cast off from the island and explore the unique nature surrounding the Florida Keys!
- Morning Special!
- Marriott Beachside Location Marriott Beachside
- 1 to 2 people Occupancy 1 to 2 people
- 90 Minute Duration 90 Minute
Join our guides at our Marriott Beachside location for a jet ski tour of the stunning waters of Key West!
- Casa Marina Location Casa Marina
- 1 to 8 hours Duration 1 to 8 hours
See the amazing marine life of Key West while “walking on water” as you glide on top of your Barefoot Billy’s paddle board.
- Marriott Beachside Location Marriott Beachside
- 1 to 8 hours Duration 1 to 8 hours
Stop by our Marriot Beachside Resort location to pick up your Key West kayak rental for a fun day on the water!
- Marriott Beachside Location Marriott Beachside
- 1 to 8 hours Duration 1 to 8 hours
Explore the stunning waters and scenery of Key West with friends and family while floating along on a paddle board!
- Casa Marina Location Casa Marina
- 1 to 8 hours Duration 1 to 8 hours
Launch right from the beach and get to know Key West from the water with a Casa Marina kayak rental!
- Reach Resort Location Reach Resort
- 1 to 2 people Occupancy 1 to 2 people
- 90 Minute Duration 90 Minute
Travel up to 26 miles around the island of Key West on this 90-minute guided jet ski tour with Barefoot Billy’s!
- Reach Resort Location Reach Resort
- 1 to 8 hours Duration 1 to 8 hours
Discover the beauty of Key West while “walking on water” with a paddleboard rental from our Reach Resort location!
- Casa Marina Location Casa Marina
- 1 to 8 hours Duration 1 to 8 hours
Sail through the beautiful crystal clear waters of Key West on a 14′ Hobie Cat sailboat!
- Casa Marina Location Casa Marina
- 1 to 8 hours Duration 1 to 8 hours
Spend an hour or a whole day out on the beautiful waters of Key West with this FunCat rental!
- Marriott Beachside Location Marriott Beachside
- 1 to 8 hours Duration 1 to 8 hours
Relax on the gorgeous waters of Key West with one of our chaise lounge catamarans at our Marriott Beachside location!
- Reach Resort Location Reach Resort
- 1 to 8 hours Duration 1 to 8 hours
Set sail on a motorized chaise lounge catamaran and soak up the sun on a Key West sailing rental.
- Reach Resort Location Reach Resort
- 1 to 8 hours Duration 1 to 8 hours
See Key West from the water with this kayak rental from our scenic Reach Resort location!
- Garrison Bight Marina Location Garrison Bight Marina
- All ages Ages All ages
- 1 to 40 people Occupancy 1 to 40 people
- 3 Hours Duration 3 Hours
Spend your morning at the sandbar and experience the turquoise waters surrounding Key West at a slower pace on this private charter.
- Garrison Bight Marina Location Garrison Bight Marina
- All ages Ages All ages
- 1 to 40 people Occupancy 1 to 40 people
- Varies Duration Varies
Snorkel, see Dolphin, or visit a sandbar with an open-air cruise for up to 40 people. Create the perfect escape with a private adventure aboard our 45-foot Corinthian catamaran!
Purchase a fantastic gift or gifts: each gift certificate is the exact value of one of our offerings, but must be used within 1 year of purchase. Gift certificates are