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Parasail In Key West

Key West's Best Parasailing Experience

Quick Details

From :

$ 89.99 $ 49.95

Key West Parasailing

As we cruise into the crystal-clear waters, tropical music sets the mood while our crew secures you comfortably into the parasail harness. When it’s time to fly, you’ll be gently lifted into the sky for a smooth, peaceful ascent.

From hundreds of feet above the water, take in breathtaking panoramic views of the Florida Keys, turquoise water below, Key West’s iconic shoreline in the distance, and often dolphins, sea turtles, or stingrays swimming beneath you.

Trip Include:

  • Longest & highest parasail flights in Key West
  • Experienced, USCG-licensed parasail crew
  • State-of-the-art parasail boats & equipment
  • Departures from downtown Key West or Smathers Beach

 

New Parasail Equipment

parasailing in key west with barefoot billys

Parasail Video

Over 2,000 Excellent Reviews!

Unforgettable Key West Experience

Parasailing with Barefoot Billy’s was hands down one of the highlights of our trip to Key West. The crew was friendly, professional, and made us feel completely safe from start to finish. The views from up top were absolutely incredible, clear turquoise water as far as you could see. Smooth ride, great music, and an experience we’ll never forget.

– TripAdvisor, 01/2026
Best Parasailing in Key West

This was our first time parasailing and Barefoot Billy’s made it perfect. The crew explained everything clearly, the equipment felt very safe, and the takeoff and landing were super smooth. Floating above the water was peaceful and the views were unreal. If you’re looking for parasailing in Key West, this is the company to book with.

– TripAdvisor
Fun and Worth Every Penny

We booked parasailing with Barefoot Billy’s based on reviews and they did not disappoint. The staff was upbeat and experienced, and the entire trip felt well organized. Being able to see Key West from that height was amazing and spotting dolphins below was the cherry on top. I would absolutely recommend this to anyone visiting the Keys.

– TripAdvisor

FAQs About Parasailing In Key West