Things To Do In Key West

Half Off Roller-Coaster Simulation at Coasters

Key West

$20 $10

Riders aboard digital roller coaster jet through distant galaxies and shark-infested waters on this 3-D ride

46% Off Harbor Day Sailing Tour

Key West

$294 $160

Up to six passengers take to the Gulf of Mexico in a 33-foot sailboat with water, soft drinks, and cooler space for BYO drinks

Up to 61% Off Organic Wine or Beer Tastings with Chocolate

Key West

$45 $20

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Guests pair organic wine or small-batch beers with gourmet chocolates while learning the history behind their rich treats

36% Off Trolley Tour

Key West

$28 $18

Riders hop on and off at nine stops along a scenic route through the streets of Key West

45% Off Outdoor Supplies

Key West

$800 $440

Local businesses like this one promote thriving, distinctive communities by offering a rich array of goods and services to locals like you

Up to 41% Off Helicopter Tour for Up to Three

Florida Keys Marathon Airport

$270 $159

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Pilots fly over Marathon, Pigeon Key, Boot Key Harbor, and portions of the Seven Mile Bridge during a 10-minute helicopter tour

Up to 46% Off Glass-Bottom-Boat Cruise

Key Largo

$70 $39

(100)

70 ft. yacht shuttles up to 129 guests, who gaze through 280 sq. ft. glass bottom at vibrant coral-reef state park

Up to 51% Off Snorkeling Trip for One or Two

Key Largo

$34 $17

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Sail to waters near John Pennekamp Coral Reef State Park and National Marine Sanctuary for an hour of fun and instruction

Up to 54% Off a Standup-Paddleboarding Lesson

Marathon Florida Keys

$55 $27

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Paddlers explore the placid ocean surface surrounding the island of Marathon while standing atop a large board

60% Off Sailing and Club Membership

Marathon

$350 $139

Club members enjoy discounts on sailing trips and merchandise

51% Off Private Sailing Trip for Up to Five

Marathon

$200 $99

Launching from Islamorada, guests relax in a historic-replica sloop and enjoy the views as well as any food and drink brought along

53% Off Introductory Sailing Lesson from Key Lime Sailing

Key Largo

$200 $95

Two-hour introductory sailing class aboard a 22-foot single-masted Catalina teaches students trimming, tacking, and jibing

Up to 56% Off Flyboard Lessons

Marco Island

$300 $145

Jetpack-like boards send riders soaring up to 30 feet in the air over the ocean

50% Off

City of Marco

$200 $100

Local businesses like this one promote thriving, distinctive communities by offering a rich array of goods and services to locals like you

Up to 57% Off Shelling Trip from Reel Kind Fishing

Goodland Boat Park

$80 $39

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Naturalist shares knowledge about ecosystem and animals while guests collect rare shells on remote islands

Select Local Merchants

Billy figured that with Key West's powdery beaches and paradisiacal waters, a business could grow itself if it supplied high-quality watersports rentals and guides who could unveil the beauty of the area. To that end, he began building a team and a fleet that would take guests on adventures both above and below water. Today, guides conduct jet-ski tours on Yamaha WaveRunners, as well as lead groups of kayakers and standup paddleboarders on tours that meander along the Atlantic, Caribbean, and Gulf of Mexico. They also lead underwater ventures, such as scuba diving and snorkeling to technicolor coral reefs and historic ships that have lost the will to float. Individual equipment rentals cater to guests who prefer independent explorations. It's this breadth of tours and rentals that has earned Barefoot Billy's a certificate of excellence from TripAdvisor.

1435 Simonton St
Key West,
FL
US

Rum, wine, beer, sun, and food: the Key West Bacchanalia celebrates summer with all five. The festival pours out tastes of Puerto Rican rum cocktails and other select drinks, which guests sip while watching celebrity chefs whip up savory cuisine in the handheld form of burgers and barbecue. Should ticket holders wish to imbibe some history as well, an Ernest Hemingway-themed event with author and Hemingway expert Philip Greene shares recipes for rum drinks that the literary superstar enjoyed during his days in Paris, Cuba, and inside a rising sun. A portion of the event's proceeds benefit the Darrell Gwynn Foundation, an organization supporting individuals with paralysis.

5130 Overseas Hwy. 1
Key West,
FL
US

Ripley’s has enthralled audiences for more than nine decades with its dedication to revealing odd and unexplainable rarities from around the globe. But it all began with one man: Robert Ripley, a wildly successful and eccentric character who rose to fame during the first half of the 20th century. After selling his first cartoon to Life magazine at age 14, he set out on a quick-paced career of drawing sports cartoons for the New York Globe. During a slow day at the office, he sketched nine unusual sporting events and finished his work with a title: “Believe It or Not!” It became immensely popular, allowing Ripley to travel the world in search of more bizarre stories to put into his comic strips. While visiting relatively unknown areas in locales such as India, China, and the inside of his neighbor’s chimney, he picked up a slew of unbelievable souvenirs that later became fixtures in several of Ripley’s museums, or as they’re affectionately called today, Odditoriums. Ripley’s now encompasses publications, attractions, a television show, and a blog, all of which carry Ripley’s tradition of reporting on the world’s curiosities.

108 Duval St
Key West,
FL
US

The hum of an engine melds with the howling wind as the 34-foot powerboat slices through the waters around Key West like an orange and blue bullet. At the helm, the captain shares his knowledge of the island’s notable sights and history, skirting the shoreline around the scenic Southernmost Point, Sunset Key and Mallory Square. Riders often spot local sea life frolicking in the tropically teal waters of the Caribbean, such as dolphins jumping or clown fish squirting unsuspecting minnows in the face with jets of air from prank lapel flowers.

0 Duval Street
Key West,
FL
US

After logging more than 1,000 hours of flying time, organizing six competitions, and gaining 34 years of experience, Scot Trueblood can safely be dubbed a hang-gliding devotee. His passion for flight is only matched by his enthusiasm to share the sky with others. That’s why he founded Paradise Hang Gliding Inc., which allows Scot to take novices for atmospheric tandem rides over the stunning waters of Florida Bay and the Straits of Florida.

As students soak up views of blue waters spread out beneath them, Scot teaches them the important aspects of operating a hang glider. He generally starts beginners off on the Wills Wing Condor 330, a glider with a lightweight frame and large wingspan. These attributes allow it to take off while moving at extremely slow speeds, ensuring a comfortable ride for hesitant newcomers or cowardly penguins.

83413 Overseas Highway
Islamorada,
FL
US

Keys Skis and Adventures' fleet of wave runners speed across the water's surface, sending plumes of liquid into the air as riders uncover some of the area's most scenic destinations. On semiprivate tours, the personal watercraft coast along local canals, open waters, and mangroves. The Key Largo area sets the stage for these aquatic adventures, granting easy access to the Atlantic Ocean. Local wildlife such as manatees, dolphins, and aquatic birds make appearances in these areas, although they rarely sign autographs.

201 Ocean Dr.
Key Largo,
FL
US