Top Key West Parasailing

Key West Parasailing - Next to Cruise Port with Amazing Views

50 minutesFree Cancellation

Parasailing over the Historic Key West Seaport

1 hourFree Cancellation

Special Offer

Parasailing in Key West at Smathers Beach

1 hourFree 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

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

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

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What are people saying about Key West

Parasailing in Key West at Smathers Beach

DEANNA_L, Sep 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

Key West Parasailing - Next to Cruise Port with Amazing Views

Kaylee_B, Aug 2026

🤩🤩🤩must do

⭐⭐⭐⭐⭐ Such an amazing experience! We did the early morning parasailing and it was absolutely perfect. The water was beautiful and calm, the views were incredible, and being out there first thing in the morning made it feel so peaceful and special. The crew was friendly, professional, and made us feel completely safe and comfortable the entire time. Everything was organized and so much fun from start to finish. Definitely one of the highlights of our trip and I would 100% recommend booking the early morning time!

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).

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

Lauren_F, Oct 2025

We went out with Sunset...

We went out with Sunset Watersports for a day at their water adventure park and we had the best time! From start to finish, the crew were fun and great to be around for the day, the activities were so fun and it was awesome to be able to have them all in one place. Lunch was amazing and very tasty, we would definitely book this again! We got lucky and even saw a few dolphins while we were out jet skiing! Special thanks to Daniel and Atticus, they were very attentive and helpful throughout the whole day.