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Parasailing in Key West

Water Sports & Parasailing in Key West

The turquoise waters of Key West are just waiting to be explored, and there are plenty of ways to do so.

From snorkeling and scuba diving to kayaking and sunset cruises, Key West has it all. Westwinds Inn is located conveniently close to local tour and watersports companies, so check them out, book a tour, and have some fun in the sun!


Experience the thrill and adventure of peacefully floating high above the tropical waters of Key West on a parasailing adventure. There are multiple tour companies offering parasailing adventures near our hotel, including Sebago Key West, Tours Key West, and Key West Parasail.

Glass-Bottom Boat Rides

Experience underwater views without getting in the water aboard a glass-bottom boat tour. These unique tours let you gaze upon a wide variety of fish and other sea creatures, and some even take you over North America’s only living coral reef. Tours are available through Fury Water Adventures, and depart from the ramp at the end of Duval Street less than a mile from our hotel.  

Dolphin Watching

Encounter dolphins in the wild with Honest Eco’s Dolphin Watch tour, the Key West original since 1986. This four-hour tour departs twice a day and has a six-passenger maximum on each tour to enhance your experience. During the tour, you can watch resident wild dolphins as they play, sleep, and hunt in the tranquil waters of Key West. The tour ends with some snorkeling at a protect spot. Each tour includes fruit, water, snorkeling, and, of course, fun!


Key West offers incredible opportunities for sport and deep-sea fishing. Enjoy fun for the whole family on a local charter, such as Too Lethal Fishing Charters or AWS Charters, or rent a boat and make your own adventure. Charters offer full- and half-day tours.

Sunset Sails

Experience the vibrant colors of a Florida sunset aboard the last wooden ship built in Key West, the Schooner Western Union. This sailboat leaves the Schooner Wharf pier every evening one hour before the sunset, and passes by the world-famous Sunset Celebration, held at Mallory Square, on its way out to the majestic Atlantic Ocean. While on board, you’ll enjoy complimentary champagne, beer, wine, soft drinks, and water; conch chowder; a free slice of Key Lime Pie; live music; and beautiful, unobstructed views of the sun setting on the horizon.

Jet Skiing

Explore the waters surrounding Key West with Barefoot Billy’s Island Jet Ski Tour. Jump on your own Yamaha Waverunner and cruise around the entire island on a two-hour excursion, which stops at various points of interest, such as The Southernmost Point, Historic Key West Bight, and Sunset Key. The tour starts with expert instruction to ensure your safety during the 27-mile ride. 

Snorkel Trips

Snorkel through a stunning coral reef and the beautiful, crystal blue waters surrounding the island paradise of Key West. Then walk on a deserted tropical beach or simply relax and unwind on a sand bar. Snorkeling tours are available through numerous local companies, include Fury Water Adventures and Sunset Watersports.

A Little Bit of Everything

Sebago Key West offers day trips that include a combination of the most popular water activities! The Snorkel & Sunset Combo (snorkeling, sunset sail, beer and wine, champagne toast), Island ‘Ting (sailing, snorkeling, kayaking, food, and drinks), and Power Adventure (sailing, snorkeling, kayaking, wave runners, parasailing, water toys, buffet, and drinks) are just a few of this company’s amazing combo options.

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Pool and garden at our key west bed and breakfast

Photo Gallery

Tour our beautiful Key West hotel through photos in our gallery. View the lush grounds and gardens, our cozy rooms, and unique features like our library and pools.

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On the Beach after a wedding in key west

Wedding Gallery

You’ve always pictured your perfect wedding day. View the photos in our Wedding Gallery to see what your destination wedding can be like at Westwinds Inn.

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Key West beach and palm tree

Calendar of Events

There’s always something going on in Key West, from food and literary festivals to fishing and sailing tournaments. View our Events Calendar for the latest happenings.

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