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Tours & Rentals

With over 20 land and sea activities on the menu – there is a guided tour or an adventure for you!¬†Want to explore Key West and its surrounding waters on your own?¬†Barefoot Billy’s offers hourly and daily rentals on recreational equipment for both land and sea.

If you can dream it, Barefoot Billy’s can make it a reality!

  • Jet Ski Tour

    Jump on one of Barefoot Billy's Yamaha Waverunners and cruise around the island on a 28 mile, 2-hour guided jet ski tour. Look out for an array of Florida Keys' wildlife as you speed your way through our Caribbean waters. Breathe in the excitement as you race from the Atlantic Ocean to the Gulf of Mexico and back to the Atlantic.

  • Flyboard

    Experience the feeling of weightlessness and a sense of freedom like no other as you fly above the water. One-on-one flight lessons on a Flyboard wil have you taking off, hovering, and landing in minutes. One of the most exhilarating experiences you can have in Key West. Discounts available for parties with multiple flyers.

  • Parasailing

    Glimpse dolphins and sea turtles playing as you soar hundreds of feet above the tranquil waters of Key West. Take in the spectacular 360-degree views and feel the warm sea breezes during this memorable parasailing adventure.

  • Clear Bottom Kayak Tour

    Join us on a fun look through the clear lens of a glass bottom kayak. Flat clear shallow water welcomes all skill levels to enjoy this 90 minute tour. Gently cruise through warm Key West waters with our marine science oriented and history loving guides.

  • Paddle Board Tour

    Observe the world on top of the water and the world beneath it at the same time. Flat clear shallow water welcomes all skill levels to enjoy this 90 minute tour. Gently cruise through warm Key West waters with our marine science oriented and history loving guides.

  • Snorkel Gear Rental

    Rent snorkel gear right on the beach and get ready to discover the beautiful underwater world of the Florida Keys. Encounter schools of tropical fish, living coral heads, sea sponges and more as you snorkel through the crystal clear waters of Key West.

  • Paddle Board Rentals

    Experience the feeling of walking on water and getting the best view of marine life at the same time. Paddle boarding provides a unique ability to observe both the world on top of the water and the world beneath it. Reserve your paddle board rental today through Barefoot Billy's.

  • Schooner Sunset Sails

    Enjoy the world-famous sunset sail aboard the majestic Schooner Western Union, the oldest working wooden schooner in the United States. There's no other sailing vessel quite like her in the world.

  • Scooters

    Discover all the hidden gems of Key West the local way! Scooters provide easy and convenient transportation to just about everything the island offers. Barefoot Billy's has 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. We offer daily and extended rentals.

  • Bar Stroll

    What do you get when you combine five of Key West's top bars, five complimentary drinks, and a free souvenir t-shirt? One unforgettable day in paradise! The Key West Bar Stroll.

  • Snorkel Trip

    Barefoot Billy's snorkel trips are the best in Key West! Snorkel North America's only living coral reef system and encounter schools of tropical fish, sea turtles and more. Barefoot Billy's provides the snorkel gear and some of the best snorkeling venues in the world.

  • Fishing

    So you want to go fishing? The waters of Key West offer up everything from tarpon and shark to grouper and wahoo. Barefoot Billy's offers up light tackle, bottom fishing, offshore, and flats fishing trips so that you can reel them in.

  • Dry Tortugas

    Experience the pirate-riddled history, the vast marine life, the clear blue-green waters, and the sheer beauty that is the Dry Tortugas National Park. Explore the living reef and search for sunken treasure with the complimentary snorkel gear or investigate Fort Jefferson and the history that lies within.

  • Kayak Rentals

    Relax and enjoy the sights and sounds of Mother Nature as you paddle through the crystal clear Caribbean waters or through unspoiled mangrove ecosystems. Barefoot Billy's kayak rentals include kayak, paddle and personal flotation devices.

  • Hobie Cats

    Imagine the sensation of having the warm trade winds fill your sail as you maneuver across the pristine waters surrounding Key West. Barefoot Billy's brings that dream into reality with hourly hobie cat rentals - book yours today!

  • Jet Ski Rentals

    With Barefoot Billy's jet ski rentals you can race through warm Caribbean waters, jump some waves, and explore Key West from the water! Hourly jet ski rentals are available - reserve some fun today.

  • Helicopter Tour

    Take an aerial tour of the most beautiful beaches, ocean life, and nature preserves that the Florida Keys has to offer on a Helicopter tour around Key West. With four different tour packages to choose from - one is sure to please every adventurer in your party.

  • Scuba Diving

    Living coral reef, diverse and plentiful marine life, and an abundance of shipwrecks are just some of the reasons that Key West is one of the most popular scuba dive destinations in the world. Book your SCUBA adventure with Barefoot Billy's today!

  • Catamaran Sunset Sail

    Watch the sky turn from blue to the most brilliant oranges, reds and yellows aboard a spacious catamaran on a famous Key West Sunset Sail. Enjoy free beer, wine and champagne.

  • Ghost Tour

    For over 16 years, the master storytellers at Key West Ghost & Mysteries Tours have been bringing the islands most bizarre and unexplained tales to life. Encounter the haunted and hidden dark side of Key West.

  • Glass Bottom Boat

    Go beneath the waters of Key West on this glass bottom boat and discover breathtaking coral formations and ocean life without getting wet. Ocean Vue Adventures delivers the wonders of the bottom of the ocean during their two-hour glass bottom boat tour.

  • Team Building

    Bring your employees together. Barefoot Billy's can organize corporate events - such as team building trips, incentive trips, etc, - combining jetski tours with sailing, parasailing, snorkeling and many other options.