Things To Do In Key West

Hop-On, Hop-Off Trolley Tour for One, Two, or Four from City View Trolley Tours (56% Off)

City View Trolley Tours

Key West

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

$28 $13

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90-Minute Ghost Tour for Two, Four, or Six from The Original Ghost Tours Key West (Up to 52% Off)

The Original Ghost Tours Key West

Key West

Guides lead family-friendly walking tours of Key West, sharing stories of the city’s paranormal history and legendary spirits

$42 $20

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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

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

$800 $400

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Two-Hour Standup-Paddleboard Tour for Two, Four, Six, or Eight at SUP Key West (46% Off)

SUP Key West

Key West

Peaceful views of Key West and regional wildlife during two-hour guided tours atop standup paddleboards

$90 $49

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Seashell Hunt and Snorkel Adventure for Four or Six from Keys Huka Dive (Up to 57% Off)

Keys Huka Dive

Marathon

Guests snorkel and hunt for seashells in groups of four or six

$700 $300

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

Florida Keys Sailing

Marathon

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

$200 $99

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$169.99 for a Key West Helicopter Tour Package for Up to 3 from Air Adventures LLC (Up to $332 Value)

Air Adventures LLC

Key West

Helicopters soar over 10 miles of immaculate Key West shoreline for a bird’s-eye view of marine life and seascapes

$332 $169.99

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Two- or Four-Hour Paddle Board or Kayak Rental for Two or Four at Key West Eco Tours (Up to 64% Off)

Key West Eco Tours

Geiger Key

Conservation-minded tour outfit provides rental equipment to explore scenic spots around Florida Keys

$50 $21

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Scuba-Diving Experience for One, Two, Four, or Six at Diving Key West (Up to 51% Off). No Certification Required.

Diving Key West

Fort Zachary Taylor State Park

Experienced divers guide divers down below the surface to experience the nature-defying wonders of scuba

$230 $125

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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 Street
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

For 30 years, Captain Bob has navigated boats across the water, a hobby that included taking local Boy Scout troops on tours of some of Key West's most scenic locales. Despite this background, Captain Bob didn’t originally intend to use his 26-foot Nordic tugboat for chartered tours. He bought the vessel, aptly named Red Bull, for him and his wife to use, but after several people asked to charter the boat, he finally gave in.

Today, Captain Bob ferries passengers on aquatic journeys through the Gulf of Mexico's pristine waters. Though the captain offers several different outings—such as snorkeling near reefs and shipwrecks—the most popular tours are the ones that encompass a little bit of everything. During these trips, Captain Bob and his crew tour the harbor, floating by Fort Zachary Taylor Historic State Park and the historic seaport before passengers take out their fishing poles and catch some dinner. Then, the captain takes groups to see playful bottlenose dolphins as they swim in their natural habitat and stick Kick Me signs on the backs of passing snorkelers. As the boat rounds back to the harbor, it floats beneath the warm colors of an ocean sunset.

With Garmin fish finders and GPS tracking, Red Bull can easily navigate Key West's waters regardless of which trip customers choose. The boat also boasts a sundeck, air-conditioned lounge, and full galley.

711 Eisenhower Drive
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