Top Key West Parasailing

Key West Parasailing - Next to Cruise Port with Amazing Views

50 minutesFree Cancellation

Soaring high above the stunning waters of Key West offers a unique perspective of this picturesque island. From the deck of a USCG-certified boat, observe vibrant coral reefs and watch for dolphins and sea turtles swimming below. With a professional crew ensuring safety and comfort, enjoy a tandem or triple flight for a shared experience that’s perfect for families or friends. Whether it's a romantic outing or a fun group adventure, the thrill of parasailing brings unforgettable memories to your Key West vacation.

Key West Parasailing Adventure with Island Time Parasail

1 hour 15 minutesFree Cancellation

This location was carefully selected to offer convenience to all guests arriving on cruise ships or those looking to parasail downtown. Situated a mere 5-minute walk from the bustling cruise ship port, our spot eliminates the hassle of shuttles and allows you to maximize your time for adventure. Imagine stepping directly off your ship and onto our parasail boat, ready and waiting to whisk you away to exhilarating heights as soon as the cruise ships dock. Say goodbye to wasted time and hello to instant thrills with us!

Key West Parasailing: Ideal For Cruise Ship & Downtown Guests

1 hourFree Cancellation

Parasailing in Key West at Smathers Beach

1 hourFree Cancellation

Parasailing over the Historic Key West Seaport

1 hourFree Cancellation

If you’re stuck choosing between activities like snorkeling and jet skiing, then this exciting full day experience will let you have fun under the sun however you want. This water sports package gives you access to a dozen different aquatic activities. Race across the water on a jet ski or banana boat. Bounce on water trampolines or inflatable slides. Snorkel, parasail, and kayak to your desire while enjoying unlimited draft beer.

Key West: Water Sports Adventure includes Jetski, Parasail, Snorkel & Waterpark

6 hoursFree Cancellation

Key West: All-Inclusive Watersports Adventure with Lunch & Beer

6 hoursFree Cancellation

Key West Ultimate Watersports Adventure with Snorkeling Upgrade

3 hours 30 minutesFree Cancellation

Smathers Beach is the largest public beach in Key West and one of the best playgrounds of watersports in the Florida Keys. This Key West Beach Pass is the ultimate ticket to fun in the sun. Do more than swim and suntan with access to multiple watersport activities. Kayaks, rafts, tubes, paddle boards, and Hobie Cat sailboats are available. This pass also includes a thrilling parasail ride.

Key West Ultimate Beach Pass with Parasailing

8 hoursFree Cancellation

Parasailing Experience in Key West

Must-Dos in Key West

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What are people saying about Key West

Key West Parasailing - Next to Cruise Port with Amazing Views

Jose_G, Oct 2026

Excursion was right at...

Excursion was right at the port as we disembarked the cruise ship, the staff was friendly, the boat was beautiful and looked well maintained, the staff explained the parasailing process thoroughly, length of excursion was just right and experience is unforgettable!

Parasailing in Key West at Smathers Beach

DEANNA_L, Sept 2026

1st time Parasailers

Logan & Wyatt took us out, & for 1st time parasailers, they treated us with the utmost respect. We had so much fun & will more than likely do it again, whether it’s here in the Florida Keys or somewhere else. Wyatt took awesome pictures of our adventure, so we have wonderful memories. We checked in with Don, who was also a hoot. And by the way, Don, we saw a key deer on the way back to Key Largo. 😊 Deanna & Rick L - Montana

Parasailing over the Historic Key West Seaport

Alicia_G, Aug 2026

You guys rock!!!

There were two guys but i only remember one’s name and it was Ian. They gave me the best experience ever. Safety precautions were mentioned with professionalism but they were so down to earth. I love the way they made us feel comfortable…the whole group at that. Thanks guys 🤞🏾✊🏾🖤💋

Key West Parasailing: Ideal For Cruise Ship & Downtown Guests

Charmell_D, Jan 2026

Amazing life changing experience

The crew was very knowledgeable, educating, professional, friendly, they went beyond the call of duty to provide an exceptional experience. It nice to work with someone who loves what they do. I would love ❤️ to experience this again with this same crew they were all amazing. Thank you for hiring such great employees

Key West Ultimate Watersports Adventure with Snorkeling Upgrade

Victoria_B, Dec 2025

100% book this trip

Truly amazing! I would 100% recommend this to anyone especially people with kids. It was so nice to be able to do so many different activities without doing each all day long. Broken up into an hour or 30 minutes depending on the activity kept the kids and my attention a lot better and kept the day fun and moving along. We drove two hours to key west from Islamorada and it was 100% worth the day trip. Plenty of time to explore key west after you get back and then head back home. I definitely recommend booking the full day the snorkeling was really cool. Staff was amazing, very friendly and made the day fun while extremely safe. The food for lunch was light and perfect (maybe bring some snacks for yourself or your kids for before and after lunch).