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89.99
$
49.95
Parasailing in Key West – Soar Above the Florida Keys
Parasailing in Key West is one of the most unforgettable ways to experience the island, and Barefoot Billy’s makes it easy, safe, and spectacular. Gently lift off from the boat and soar hundreds of feet above the crystal-clear waters of the Florida Keys, where panoramic views stretch from downtown Key West to the open ocean. This peaceful, floating experience is perfect for first-timers, families, couples, and anyone looking to see the island from a whole new perspective.
Trip Includes:
- 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
Why Parasailing Is One of the Best Things to Do in Key West
Key West parasailing offers a rare combination of excitement and relaxation. Unlike high-adrenaline thrill rides, parasailing is smooth, calm, and surprisingly serene. As you rise into the sky, the noise fades away and you’re left with incredible views, ocean breezes, and a feeling of total freedom. It’s consistently rated as one of the top activities in Key West because it’s safe, accessible, and unforgettable.
Parasailing for Couples, Families & First-Timers
Parasailing is one of the most versatile activities in Key West and is suitable for a wide range of guests.
Tandem & Triple Flights
Depending on wind conditions and combined weight, two or three guests can often parasail together. Tandem and triple flights are a popular choice for couples, friends, and families.
Great for Kids & Families
Parasailing is family-friendly, and children can often participate as long as they meet minimum weight requirements and feel comfortable. It’s a memorable experience for kids and parents alike.
No Experience Required
You don’t need any prior experience to parasail. Our crew handles everything, so all you have to do is relax and enjoy the ride.
New Parasail Equipment
FAQs About Parasailing In Key West
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Most parasailing flights in Key West reach 300 feet above the water, offering panoramic views of the island, coastline, and turquoise ocean below. The height provides a peaceful, floating sensation rather than a thrill ride.
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No experience is required to parasail in Key West. The crew handles everything, from harnessing you in to launching and landing, making it perfect for first-timers and all comfort levels.
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A typical parasailing trip lasts about 1 hour, with each flight averaging 8–15 minutes in the air. The rest of the time is spent cruising on the water and enjoying views while others fly.
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Yes, parasailing in Key West is often done tandem or triple, depending on wind conditions and total weight. Flying together is a popular option for couples, friends, and families.
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Wear comfortable clothing or swimwear and plan to go barefoot. You’ll stay mostly dry unless you choose a gentle dip at the end of your flight.
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Yes, parasailing in Key West is very safe when operated by experienced crews using modern equipment and established safety procedures. Tours are weather-monitored and designed for smooth takeoffs and landings directly from the boat.
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Yes, parasailing has a max combined weight of 500lbs between all of the flyers. The crew will always adjust pairings and flight plans to ensure a safe and enjoyable experience.
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Yes, parasailing is family-friendly, and children can fly as long as they meet the minimum weight requirements and are comfortable participating. Many families consider parasailing one of the most memorable activities in Key West.
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From the sky, you’ll see crystal-clear water, boats, beaches, and often marine life like dolphins, rays, and sea turtles. Parasailing offers one of the best aerial views in Key West.
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Morning parasailing often provides calmer winds and smoother flights, while afternoon trips offer warmer temperatures and vibrant island activity below. Both times deliver incredible views and unforgettable experiences.