Things To Do In Key West

Paddleboard Rental for Two or Four, or Eco Paddle Tour for Two from Gnarly Harley Paddle (Up to 55% Off)

Gnarly Harley Paddle

Marathon

$80 $36

Hitch a ride to the beach for an intro lesson and two hours of paddleboarding, or follow your guide to a secluded island for snorkeling

$160 for 90-Minute Harbor Day Sailing Tour for Up to Six from Sunset Sail Key West ($294 Value)

Sunset Sail Key West

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

Chocolate with Wine or Beer for One or Two, or Chocolate Making with Wine for Two at Lush Bar (Up to 50% Off)

Lush Bar

Key West

$55 $30

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Guests pair wine or beer with gourmet chocolates while learning the history behind their rich treats, or make their own chocolate bars

Hop-On, Hop-Off Trolley Tour for One, Two, or Four from City View Trolley Tours (36% Off)

City View Trolley Tours

Key West

$28 $18

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

Two-Hour Sunset Sail for Two, Four, or Six from Florida Keys Sailing (Up to 52% Off)

Florida Keys Sailing

Marathon

$200 $99

On an air-conditioned boat, passengers can bring coolers of food or drinks and even take the helm, if they wish

Four-Hour Reef Fishing or Tarpon Fishing Trip from Ware's The Fish Charters (Up to 50% Off)

Ware's The Fish Charters

Key West

$800 $400

Enjoy a four-hour voyage on a chartered fishing vessel off the coast of Key West as you hunt for tarpon

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, spirits, music, 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. A portion of the event's proceeds benefit the Darrell Gwynn Foundation, an organization supporting individuals with paralysis.

5130 U.S. 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

"Opulent and luxurious" or "a heavy drinker" are two ways the dictionary defines the term lush. But at Lush Bar, they've got their own definition: "One who becomes luxuriously intoxicated after a glass of wine and flirts with everyone to save the planet." However you define the term, luxury certainly comes to mind at Lush Bar. The airiness brought on by the beach-inspired decor and tall, white walls is offset by a menu of rich, decadent treats. But whether indulging in wine, beer, or chocolate, you can always feel good about your selection. That's because everything here is organic: from the wine all the way down to the coffee and Arbor teas. Lush Bar also hosts weekly pairings that explore the history of chocolate, which—contrary to popular belief—has nothing to do with singing men in matching overalls.

1130 Duval St.
Key West,
FL
US

To call the restoration of the High Tide a labor of love would be to greatly devalue the definition of "labor." The 33-foot sloop remained on land for almost a year and a half as a team, mostly volunteers, returned the 1978-construction vessel to like-new status. Now, with Captain Seth at its open cockpit, the High Tide dips its fiberglass hull back into the waters of Key West, unfurls its sails, and embarks for the horizon. Whether on trips to admire the sunset, snorkel in the Gulf of Mexico, or test a new brand of motion sickness medication, the sailboat provides noiseless passage, save for the flap of canvas on the breeze.

202 William Street
Key West,
FL
US

It?s not an energy drink, a crimson bovine, or even a particularly misguided spelling of ?bread bowl.? Rather, the Red Bull is a 26-foot-long, cherry-red Nordic tugboat, and it provides a unique way to rub metaphorical elbows with the Florida Key's aquatic wildlife and sea birds. Clients can charter the boat for a historic tour of the harbor, and get a watery glimpse at the seaport, Mallory Square, and the Sand Key lighthouse. Or, they can commission Captain Bob and his crew to chauffeur them on dolphin-spotting excursions. The Red Bull is also available for fishing trips, and is equipped with a state-of-the-art fish finder.

1102 Duval St
Key West,
FL
US