Things To Do In Key West

50% Off a Flyboard Experience

Barefoot Billy's

Casa Marina Resort

$199 $99

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

Up to 55% Off Paddleboarding and Snorkeling

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

Up to 52% Off Fishing Trips

Red Bull of Key West

Key West

$300 $149

Cheery red tugboat takes pairs or groups for fishing trips in the waters around the Florida Keys

64% Off Burger Wars and Unlimited Cocktails Event

Key West Bacchanalia

Key West

$69 $25

Puerto Rican rum cocktails shine while local and celebrity chefs spar for the best bite during a burger war and beverage tasting bacchanalia

46% Off Harbor Day Sailing Tour

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

45% Off Outdoor Supplies

Ware's The Fish Charters

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 50% Off Organic Wine or Beer Tastings with Chocolate

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

Select Local Merchants

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.

202 Duval St.
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 St
Key West,
FL
US

On many windy, sun-drenched days in the Florida Keys, an electric catamaran flying the colors of the America Sailing & Diving Club can be seen escorting revelers across ocean waves. Formed in 1973, the club brings together boat owners as well as nonowners who can set sail on the club’s fleet of sailboats that range in size from 22 feet to 44 feet, each designed to keep the club’s carbon footprint to a minimum. The club also offers courses that teach landlubbers basic sailing techniques, such as knot-tying skills so they needn’t fear that their loose engagement ring will fall overboard.

12399 Overseas Highway
Marathon Key,
FL
US

Captain Alfons of ParaWest Parasailing knows the sky over Cayo Hueso almost as well as he knows its waters. For more than 10 years the Coast Guard–licensed captain has sent passengers into the crystal blue above the horizon, and dipped them into the crystal blue below. Although single and tandem rides begin and end on the dryness of the vessel, the captain and his CPR-trained crew dip riders into the water upon request. They also equip their participants with safety tips before takeoff, including such sage wisdom as "don't fly with scissors."

700 Front St
Key West,
FL
US