Activities in Key West

Two-Hour Standup-Paddleboard Tour for Two, Four, Six, or Eight at SUP Key West (39% Off)

SUP Key West

Key West

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

$90 $55

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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- 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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$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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30-Minute Flyboard Experience with Optional 120-Minute Kayak Rental from Barefoot Billy's (50% Off)

Barefoot Billy's

Casa Marina Resort

Jetlev R200 water-propelled jet pack sends its wearer above the water and into the air; kayak grants leisurely exploration

$199 $99

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$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

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

$294 $160

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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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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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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

The professional pilots at Timberview Helicopters ferry passengers high into the clouds aboard a sky-scraping whirlybird during flight tours through Destin, Kansas City, and Key West. Having chartered flights for National Geographic and the Travel Channel, these pilots expertly navigate planes toward sweeping, picturesque views, allowing sightseers to steal glances of Fort Walton Beach, downtown Kansas City, and Key West's ocean views from a perspective normally reserved for birds and astronauts with binoculars. Additionally, their high-definition videos grant guests a lasting commemoration of their in-flight experience. When they're not chartering tours, they teach budding pilots the gravity-defying tricks of their trade through pilot training and lug precious shipments from port to port with their cargo-lifting services.

3471 South Roosevelt Boulevard
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

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 Street
Key West,
FL
US