Parasailing in Key West, Florida

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Parasailing in Key West was one of the highlights of our first trip to the island. Jeff and I flew tandem with Sebago Watersports, and from check-in to landing, everything went incredibly smoothly. The views were breathtaking, we spotted a couple of sea turtles and a spotted eagle ray jumping out of the water below us, and best of all? I didn’t have to get wet. At. All!

Jeff strapped in a parasailing chute.

If you’re thinking about parasailing in Key West for the first time, here’s what our experience was like, plus a few tips to help you make the most of your flight.

Lynda strapped in a parasailing chute.

Our Parasailing Experience with Sebago Watersports

We booked our flight through Sebago Watersports and weren’t disappointed. The crew was professional and friendly, and they made the whole experience easy and enjoyable.

Parasail boarding sign on a post at a Key West marina, with boat masts in the background.

Before the trip, we signed a waiver, which is standard. We arrived 30 minutes early to check in at their office at 205 Elizabeth Street in the Historic Key West Seaport, then made our way to the boat.

The Sky Wizard boat with a parasail.

Once on board, we put on our life jackets and got a safety briefing. The crew checked our harnesses, got the parasail ready, and up we went!

A parasailing chute being inflated.

Because we flew tandem, Jeff and I got to share the whole experience side by side.

Jeff and Lynda starting to take off parasailing.

The views from up in the air were spectacular, and we felt completely safe the entire time. When it was over, the crew gently reeled us back to the boat for a completely dry landing, just like our dry takeoff.

Young man holding fake scissors pretending he is going to cut a parasailing line.

We paid extra for digital photos, and they were definitely worth it, since they’re the best souvenir of the experience.

Young photographer on a boat taking pictures.

Sebago also offers other water activities, like snorkeling and jet skiing, if you want to plan more adventures.

Southernmost Point plaque being held up in front of people parasailing.

If you’re looking for a safe and unforgettable parasailing adventure in Key West, we highly recommend Sebago Watersports.

Toy shark positioned to look like it is jumping out of the water to eat people who are parasailing.

Tips for First-Time Parasailers

  • Book early. Popular time slots fill up, especially during busy seasons.
  • Listen carefully during the safety briefing. The crew will explain how the equipment works and what to expect.
  • Want to stay dry? Tell the crew. Many crews can give you a dip in the water if you want one, or keep you dry if you don’t. We stayed dry from takeoff to landing!
  • Dress comfortably, and wear sunscreen. Leave loose items and valuables behind, since anything that falls is gone for good.
  • Consider flying tandem. Sharing the flight made it even more fun, and it’s a great option if you’re a little nervous.
  • Buy the photos. You won’t regret having pictures of yourselves soaring over the water.
  • Tip the crew. Tipping 15 to 20 percent is customary.

Final Call

After soaring over the turquoise waters of Key West, keep the adventure going with more island favorites. Meet the famous six-toed cats at the Ernest Hemingway House, get up close with sea turtles and sharks at the Key West Aquarium, or taste your way around the island on the Key West Food Tour. And for a look at our whole trip, see First Time in Key West.

Have you gone parasailing in Key West, or are you planning your first flight? Tell me in the comments: are you Team Dip-in-the-Water or Team Stay-Dry-At-All-Costs like me? And if this post helped you plan your trip, share it with a friend who’s ready to take flight!

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