The 9 Best Parasailing Tours in Key West

1.Key West Parasailing Adventure above Emerald Blue Waters

★★★★★★★★★★5.0 · 387 reviews · 50 minutes (approx.) · from $53Our pick

From Fury’s pier at 241 Front St., you’ll fly about 300 feet above Key West for 8 to 10 minutes. Tandem and triple flights are available, with dry takeoffs or an optional ocean dip. Crew members such as Abby, Alex, and Garrison help first timers feel at ease, and photos can be bought afterward.

“Wonderful experience. Abby was amazing with her photos and great value for the price. It was perfect.”

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2.Parasailing over the Historic Key West Seaport

★★★★★★★★★★4.5 · 210 reviews · 1 hour (approx.) · from $49Best value

Fly above Key West Seaport with Sunset Watersports, Florida’s original parasailing company. Expect up to an hour on the boat, an 8 to 15 minute flight, views toward the Florida Keys National Marine Sanctuary, and the option to touch the water. Singles, doubles, and triples can ride together.

“They open at 8 and the pricing is different for different times. The Logan’s were great. They explained how the flights would work and asked if we wanted to touch the water. It was such a neat experience and we would love to do it again. We heartily recommend this experience!”

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3.Parasailing Above the Island Paradise

★★★★★★★★★★4.7 · 146 reviews · 1 hour · from $54

Meet Fury’s crew at Opal Key Marina for a one-hour parasailing trip above Key West. Fly tandem or in a captain-approved group of three, enjoy a gentle boat launch, and request an optional ocean dip. Captains including Tony, Alex, and Tom have helped first-timers feel at ease.

“Guide and captain were amazing. Made us feel so welcome, upbeat, happy. Our first time and we felt 100% safe with them confident with their skills. They treated us like people not another number. Abby took amazing pics we will cherish!”

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4.Parasailing in Key West at Smathers Beach

★★★★★★★★★★4.5 · 132 reviews · 1 hour (approx.) · from $49

Meet Sunset Watersports at Smathers Beach for a one-hour parasailing trip above Key West and the Florida Keys National Marine Sanctuary. A crew such as Joey, Ian, Logan, or Captain Sean handles the safety briefing and flight, with optional toe-dipping and photos or video available to buy.

“Ian and Joey were the absolute best! They made everyone feel safe, helped cast aside any doubts and made sure the best experience was had.”

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5.Parasail Adventure in Marathon

★★★★★★★★★★5.0 · 58 reviews · from $120

Meet Captain Ian and the Land's End Adventures crew at 1 Knights Key Boulevard in Marathon. After a safety briefing, fly in groups of two or three, 300 feet above the Keys for about 10 minutes. The full boat trip lasts roughly an hour and carries no more than 12 people.

“Nothing was good, turned up having booked a month in advance to find that our booking had allegedly not been received but they had still taken payment. No alternative was offered, shocking service do not use”

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6.Key West Parasailing: Ideal For Cruise Ship & Downtown Guests

★★★★★★★★★★5.0 · 40 reviews · 1 hour (approx.) · from $49

Fly high above Key West Harbor with Sunset Watersports on a roughly one-hour trip from 201 William Street. You get a long parasail flight, views of the Florida Keys, and a possible toe-dip. The crew handles first-timers well, and the boat holds up to 12 people.

“Do not book. Very rude, paid to change the time and they said it was not paid. I showed them where it had been taken out of my account, they said I must have purchased something else. I didn't.”

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7.Ultimate Parasailing Experience

★★★★★★★★★★4.7 · 34 reviews · 1 hour · from $84

You’ll spend up to an hour on the water with Key West parasailing experts, then rise high for as much as 15 minutes in the air. Expect new equipment, a choice of departure points, and optional onboard photos. English-speaking crew guide you through the flight.

“Great with my 12 year old daughter. Ot was her first time parasailing!”

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8.Key West Ultimate Beach Pass with Parasailing

★★★★★★★★★★4.0 · 24 reviews · 8 hours (approx.) · from $109

Meet Sunset Watersports at Smathers Beach for an all-day pass with kayaks, paddleboards, rafts, tubes, Hobie Cats, and one parasail flight. You can relax on the beach between activities, take photos at Mile Marker 0, and ask friendly staff such as Shy for help with the equipment.

“The guys working there especially Shy were really friendly. They helped us with the cataterman and paddle boards”

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9.Key West Parasailing at Smathers Beach

★★★★★★★★★★4.9 · 13 reviews · 1 hour · from $84

From Smathers Beach, Sunset Watersports takes you above Key West beneath a red, white, and blue parasail. Expect about an hour on the water, a gentle dip into the sea, and views from more than 300 feet up. Joey and Marty are among the crew members praised for their safe, friendly service.

“I like being up in the air but mostly being dipped into the water.”

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