You'll spend 8 to 15 minutes airborne over the Key West Seaport, with up to an hour total on a licensed, insured parasail boat. The crew handles all the gear and timing; you just fly and look. Optional toe-dip in the water and photo packages are available on the boat.
The boat lifts you so fast you don't have time to second-guess it. One second you're strapped into the harness on the deck of the parasail boat, the next you're climbing higher, and Key West shrinks below you—the seaport, the docks, the water turning from turquoise to deep blue. The flight time runs 8 to 15 minutes, which sounds short until you're up there and realize you're not thinking about time at all. You're just looking. Sunset Watersports has been running parasailing in Key West for over 36 years, and it shows in how smooth the whole thing moves—the crew knows exactly how to get you geared up, how to time the lift, how to make the scariest part feel routine.
The boat itself is state-of-the-art, which matters more than it sounds. You spend up to an hour on the water total, so the ride out and back aren't cramped or rough. On the way back, people usually ask the captain about the dip—you can request it, and he'll lower you just enough to touch your toes to the water if you want. It's optional, but most people do it. The whole thing is built so you're not white-knuckling it; you're actually floating and looking around. Bring a camera or a GoPro if you want to capture it yourself, or ask the crew about their photo package on the boat.
Key West parasailing from this company means you're getting the longest flight time on the island. That's not marketing—it's the difference between a quick adrenaline hit and actually having time to see what's below you. The seaport is one of the most beautiful angles of the island from above, and the crew makes sure you know where to look.
Operated by Sunset Watersports
Is this one for you?Best for anyone who wants to see Key West from above without arranging their own boat or worrying about safety details—the licensed crew and 36 years of local experience mean you just show up and fly.
Same experience, different operators — compare price, rating and length.
Key West Parasailing: 8-15 Min Flight & Seaport Views★ 4.65 (238)1hENUS$ 64
Key West: Smathers Beach Parasailing with State-of-the-Art BoatsFeel the wind above Smathers Beach in Key West, parasailing with seasoned local crews. Includes all gear, safety briefing, and options for photos or GoPro shots.★ 4.73 (154)1hENUS$ 86View ›
Key West: Kayak, Snorkel & Schooner Sunset Small Group TourSet sail from Key West for kayaking, snorkeling, and sunset views in a small group. Includes snacks, drinks, gear, and local guide—relaxed adventure on the water.★ 4.90 (1,819)4h 30mENUS$ 125View ›
Key West: Morning Reef Snorkeling Tour with Breakfast & MimosasStart your Key West morning sailing to the living reef, snorkeling with tropical fish, and enjoying breakfast and mimosas on a fast catamaran. Includes all gear.★ 4.48 (728)3hENUS$ 54View ›
Key West: Reef Snorkel & Sunset Cruise with Beer & Wine3-hour snorkel tour at two Key West reefs with equipment, then sunset cruise with unlimited beer and wine. Small catamaran, all fitness levels.★ 4.70 (200)3hENUS$ 75View ›
Key West Morning Snorkel Sail & Gourmet BreakfastMorning catamaran snorkel tour from Key West with gourmet breakfast, unlimited mimosas & reef exploration. Small group, 4-5 hours, snorkel gear included.★ 4.69 (196)3hENUS$ 49View ›
Key West Bike Tour: Old Town & Southernmost Point in 2 HoursGuided 2-hour bike tour of Key West's Old Town, top landmarks, and Southernmost Point. Includes water, Key Lime pie, and local guide. Voted #1 land excursion 10 years running.★ 4.94 (2,728)2hENUS$ 59View ›
Key West: Old Town Food Walking Tour & Cuban LunchFollow a local guide through Key West’s Old Town, tasting Cuban classics, fresh seafood, and Key Lime Pie at family-run spots. Includes lunch and drinks.★ 4.89 (1,926)3hENUS$ 94View ›
Key West Sunset Sail: Dolphins, Wine & TapasLuxury catamaran sunset sail from Key West's Historic Seaport with live dolphin watching, premium wine, and chef's tapas. Small groups, 2.5 hours.★ 4.64 (761)2h 30mENUS$ 89View ›
Key West Sunset Sail with Open Bar, Live Music & Hors d'oeuvresCatamaran sunset sail in Key West with open bar, live music and appetizers. Two-hour cruise includes well drinks, wine, champagne and food.★ 4.52 (401)2hENUS$ 77View ›
Key West: Sailing & Snorkeling Tour with Craft DrinksFeel the breeze on a Key West sailing & snorkeling tour to the living coral reef. Small groups, drinks included, local guide, all gear provided—book your spot.★ 4.73 (248)3hENUS$ 79View ›
Key West: Island Jet Ski Tour & Southernmost Point RideFeel the salt on your skin as you circle Key West by jet ski, stop at the Southernmost Point, and play on a sandbar with a local guide—includes towels & life jackets.★ 4.93 (371)1h 30mENUS$ 140per groupView ›
Key West: Sunset Sail with Champagne & Harbor ViewsWatch Key West’s famous sunset from the water with a small group, champagne or craft beer in hand, and see the harbor’s lively celebration. Includes drinks onboard.★ 4.86 (983)1h 30mENUS$ 79View › Key West Parasailing: 8-15 Min Flight & Seaport Views
1h · EN
from US$ 64 per person
★★★★★★★★★★4.65238 reviews