The Most Fun in Key West!

Jet Ski Tours • Snorkeling • Sunset Sails

Go Barefoot!

Tours & Rentals

Make the most of your Key West vacation with a Barefoot Billy’s adventure on the water. Circle Key West on our famous Island Jet Ski Tour. Go on a dolphin watch and snorkel tropical waters. Relax on our dazzling Key West sunset sail. Or fly through the air on our water-jet powered Flyboard experience. Barefoot Billy’s also rents top-notch toys for getting around Key West on land and sea.

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Island Jet Ski Tour

Circle Key West in two hours and experience a unique perspective as you glide from the Atlantic Ocean to the Gulf of Mexico and back to the Atlantic.

Jump on one of Barefoot Billy’s Yamaha Waverunners and cruise around the island on a 2-hour guided jet ski tour. Look out for an array of Florida Keys’ wildlife as you speed your way through our Caribbean waters.

The tour begins with safety instructions from our expert guides, providing you with the confidence to get the most out of your island jet ski experience. Once comfortable with your jet ski, you will follow your knowledgeable guide on a 27 mile course, completely circumnavigating Key West, a task impossible by most watercraft.

During your jet ski tour, you will take in breathtaking views and watch Florida Keys marine life frolicking in the Caribbean waters. Your guide will make five stops at various points of interest, including The Southernmost Point, Historic Key West Bight, and Sunset Key.

The Island Jet Ski Tour is available several times throughout the day at our 2 locations in Key West. Select a time and location when booking online or just give us a call.




You must be 18 years or older to drive solo and present a valid photo ID. The State of Florida requires all drivers born on or after January 1, 1988 to have successfully completed a valid safe boating course. We offer the course for the really nominal fee of $3. Please arrive at least an hour before your tour if you need to complete the safe boating course. Drivers 14 years or older permitted with an adult passenger satisfying these requirements. Any age can be a passenger. Please call us with any questions.

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Seabreeze Dolphin & Snorkel Tour

Discover local Dolphins and snorkel Key West’s Backcountry.

Search for Key West’s dolphins while cruising the crystal clear backcountry waters of the Gulf of Mexico. On this family-friendly outing, observe dolphins and other Keys wildlife cavorting in their natural habitat among deserted tropical islands and snorkel Key West's warm, gentle backcountry waters.

You'll enjoy the crystal clear waters on Barefoot Billy’s Seabreeze catamaran. Bask in the tropical sun or relax in the covered shade with plenty of seating available. Enjoy a variety of complimentary fresh fruit, snacks, soda, juice and bottled water. For your convenience, there is a large head (bathroom) below deck.

Barefoot Billy’s captains and mates are well versed in Key West’s ecology with its abundant wildlife. During your tour they share their knowledge with you, providing time for you to ask questions, gaining new insights into our tropical paradise. Every trip is different as we sail along searching for dolphins and appreciating whatever Mother Nature offers up on any given day - dolphins, eagle rays, sea turtles, ospreys, frigate birds and migratory birds.

After your dolphin watch is complete its time for you to snorkel Key West’s balmy waters. Jump in and discover the natural beauty under the sea. Starfish, rays, turtles, conch, corals, sponges, and tropical fish. Never snorkeled? No problem, all equipment is provided along with expert instruction. We also have kayaks and paddle-boards available for above the water fun. Come back aboard and wash off with our fresh-water rinse. Refresh yourself with a cold drink and relax in the shade.

Book early as we limit this tour to 40 guests, well below boat capacity, to provide a spacious setting for everyone.

While dolphin pods are numerous in Key West's backcountry and often seen, we can’t guarantee dolphin sightings on every trip.


Sailing every day from the Casa Marina Resort.
Check in 11:30PM at Barefoot Billy’s Beach House.

Depart 12:00PM – Return 3:30PM

This tour includes fresh fruit, soda, juice, bottled water, snorkel gear, flotation vest and professional instruction.

Children 12 & Under
Seniors & Military




Senior Discount valid for persons 65 years or older. Please present valid ID for Military discount.

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Private charters are also available with advance reservations. It's the perfect Key West charter for a family reunion, birthday party, wedding celebration or any other special occasion.

Footloose Waldorf Astoria Sunset Sail

Celebrate the end of the day in style with a spectacular Key West Sunset Sail.

Sail into a Key West sunset aboard Barefoot Billy’s 40 foot catamaran, Footloose. Our magnificent sunsets are best appreciated from the turquoise waters and will be a highlight of your Key West vacation. Footloose provides a spacious setting, never filled to capacity, leaving ample room for you to stretch out and unwind.

Savor complimentary hors d’oeuvres while sailing Key West’s balmy seas. Our world famous Key West Pink Shrimp are featured nightly accompanied by an ever-changing variety of premium appetizers. Indulge in our complimentary selection of fine wine, premium beer, prosecco and soft drinks.

Departing from Casa Marina’s pier, your sunset sail takes you on a unique path apart from the rush of boats leaving from downtown Key West. Relax and revel in a carefree sail where the Atlantic Ocean meets the Gulf of Mexico. Take in the magnificent water views. Look for Key West's favorite attraction - the Southernmost Point buoy marking the most southern location in the United States. Sail past the Civil War era Fort Zachary Taylor and the historic navigation point that marks the way to Cuba.

Raise a toast to the sky as the sun begins its radiant descent towards the horizon. As darkness replaces the light, celebrate this special moment with your friends and family.

Book early. This tour is limited to 30 guests to provide a spacious setting for everyone.


Sailing daily from the Casa Marina Resort Pier.

Times may vary during seasons, please confirm your check-in time when booking this trip. Please check in ½ hour before departure at Barefoot Billy's Beach House.

Winter Departure 4:30PM - Return 6:30PM
Summer Departure 6:30PM - Return 8:30PM

This tour includes hors d’oeuvres, fine wine, premium beer, prosecco, and soft drinks.



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Your own private Key West sunset sail is the ideal way to celebrate a special occasion. Contact us to arrange private charters.

Flyboard Experience

The Thrill of weightlessness and a sense of freedom like no other as you fly above the water.

Soar above Key West's waters on the Flyboard - only available at Barefoot Billy's! This extreme water sport lets you fly like a Super Hero. Enjoy freedom and weightlessness in a totally new way. We provide the equipment and expert instruction, you add the fun. Unlike anything else you can do in Key West!

Never used a Flyboard? It's easy! Flyboard is an amazing activity that anyone can do. Don't pass up this opportunity - your one-on-one flight lessons with our expert instructors will teach you to take-off, turn, hover and land. In minutes, you will learn the basics for a mind-blowing flight over crystal clear waters. After mastering the basics, repeat riders can learn tricks like spins and "chasing the ski."

How does the Flyboard work? It operates as your own jetpack, propelled by a hose attached to a jet ski. Water from the jet ski is channeled to nozzles under the wakeboard style boots. You control the height and maneuvers with your lower body, similar to skate or snow boarding.

Restrictions: We care about your safety and restrict riders to age 18 and up, maximum shoe size 12 (for the Flyboard boots), and a maximum weight of 250 lbs. We also ask that you use common sense and don't go on the Flyboard if you are pregnant or have a bad neck, back or knees.


Available daily at the Casa Marina Resort, offered every hour on the half hour.



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Land & Sea Rentals

Whether you want to play on land or sea, Barefoot Billy’s has got you covered.

Rent a scooter from Barefoot Billy’s and discover Key West’s hidden gems the locals way. The narrow streets and very limited parking in Key West make traveling by scooter one of the best ways to get around the island. Barefoot Billy’s has one and two-person scooters with daily and extended rental plans.

bicycle rentals

Barefoot Billy’s bicycle rentals are the perfect way to see Key West at your own pace! Cruise around the island with ease on one of our rental beach cruisers. Plus, you will never have a problem finding a place to park. Barefoot Billy’s offers many different styles of bicycles to fit a variety of skill levels and riding styles, as well as daily and extended rental plans.

kayak rentals

Rent a kayak from Barefoot Billy’s and push off right from the beach to begin your journey through some of the most gorgeous scenery and waters in America. Experience what makes kayaking one of Key West’s most popular activities. Barefoot Billy’s kayak rentals include kayak, paddle and personal flotation devices.

paddleboard rentals

Experience the feeling of walking on water and getting the best view of marine life at the same time with a Paddle Board rental from Barefoot Billy’s. Paddle boarding provides a unique ability to observe both the world on top of the water and the world beneath it. Paddle boarding is easy, fun, and a great way to work off those Key West cocktails.

hobie cat rentals
Hobie Cats

Sail away on a Hobie Cat rental from Barefoot Billy’s! Imagine the sensation of having the warm trade winds fill your sail as you maneuver across the pristine waters surrounding Key West. Starting your sailing adventure is super easy with Barefoot Billy’s – you can rent right on the beach and we even provide instruction to help get you going.

jet-ski rentals

Want some high power fun on your own personal watercraft? With Barefoot Billy’s jet ski rentals you can do just that! Jump onto one of Barefoot Billy’s jet skis, race through the warm Caribbean waters and jump some waves. Hourly rentals for both single and double riders are available from Barefoot Billy’s.

Rentals and availability vary by location. Find out more about our rentals by talking with a Barefoot Billy’s Key West expert. We're available 7 days a week 8AM to 10PM Eastern Time, to answer questions and assist you with all of your Key West rentals.

Call 305-900-3088

2 Locations in Key West

Barefoot Billy’s has two great waterfront locations in Key West so you can get on the water faster!

Free island pickup & return for guests of the Island Jet Ski Tour.

Casa Marina Resort

At the corner of Seminole and Alberta.

Reach Resort

At the corner of Vernon and Waddell.

Everybody Loves to Go Barefoot in Key West

For over 20 years Barefoot Billy’s is a leader in tours, recreational equipment rentals and providing Key West visitors with the island’s most exciting adventures, both on water and on land. While Barefoot Billy’s is world famous for our Island Jet Ski Tour, we offer much more. Whether it’s skimming the water on a paddle board, soaking in Key West’s world famous sunset on a boat, or many more exciting adventures, Billy can make it happen. With Barefoot Billy’s you can count on quality, safety and a great time.


Need some help deciding which tours are right for you? You can contact Barefoot Billy’s fun specialists by phone or email for assistance. Give us a call at 305-900-3088. Or get on the Coconut Internet and drop us an email, check out our Facebook page, and read all the great reviews of Barefoot Billy’s on TripAdvisor and Yelp.

Ready to Go Barefoot

Ready to book your exciting Barefoot Billy’s tour on Key West’s beautiful Caribbean waters? Our simple online booking button next to each tour will have you on the water in no time. Or call a friendly Barefoot Billy’s fun specialist who is ready to help you customize your Key West vacation activities. We are available 7 days a week 8AM to 10PM Eastern Time, to answer all your questions and assist you with reserving tours or rentals.

Use Coupon Code - "Barefoot"

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You can also book your adventure by stopping by our 2 convenient locations – Casa Marina Resort or the Reach Resort. And of course you can always book a Barefoot Billy’s adventure with the concierge at your hotel and be sure to tell them Billy sent you.