What to Expect When You Go Parasailing for the First Time

Parasailing – I’d never really considered doing it but when the idea got into my head, there was no getting rid of it. I was preparing for a trip to Key West ahead of my 30th birthday and I somehow decided parasailing would a fun new thing to try.  I like going on the water and taking in views and this was an exciting, yet simple way to do just that.

If you’re considering parasailing and wondering what it actually feels like or if it’s scary, keep reading!

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Parasailing in Key West

A number of companies in Key West offer parasailing experiences including Fury Water Adventures, Sunset Watersports, Parawest and Sebago Watersports.  I decided on Sunset partly because they do single rides and I was travelling alone. (I wanted photos for the gram and I didn’t want a stranger in them. #sorrynotsorry) The trip cost US$45 and the actual time in the air lasts around 10 minutes. The time you spend on the boat depends on how many people are going.

I originally booked a 5 PM sail but it got cancelled because it was too windy. I didn’t know it at the time but it’s best to go as early as possible when the wind isn’t as strong and it’s safer. I rescheduled for 9 a.m. the next day but that started out kinda shaky as well.

When I got on the boat, the captain informed me that if no one else came he wouldn’t be able to take me alone because of the winds. Sigh. You can imagine how I felt. I kept hoping other people would show up because it was my last day in Key West and I really wanted this experience. Luckily, another couple arrived and it was decided that they would have their double ride and then I would go up with one of them. Ok, cool, a stranger can be artfully and carefully cropped out, right?

The boat is manned by two people: the captain and a crew member who explains everything, gets you suited up and takes photos and videos while you’re in the air.

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The Parasailing Experience

We were given our lifevests and harnesses in preparation for being attached to the parachute. The crew member will ask if you want to be “dipped” on your way back in so you can get wet if you want. I opted not to get dipped.

The couple went first and watching their experience calmed my nerves. It seemed simple enough. You sit on the back of the boat, get your harness attached to the parachute, and then it’s up and away.  On your return, you have to keep your legs straight out as if you’re going to sit on the boat.

When it was my turn, I was paired with the guy.  I started out grabbing the straps tightly because honestly. it doesn’t FEEL like you’re in there all tight and snug. I soon realized that it was all quite secure and that it’s not at all a scary experience. It’s more like you’re gently floating and you can just relax and take in the scenery.  If you’re paired with a stranger, just be prepared for them to ask questions about what you do for a living and where they should stay when they visit your country. That was a minor distraction for me because then I had to look over and chat when I just really wanted to soak in the experience. Overall though, I enjoyed it!

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Plus the photographer knew to take photos with just me in them so I didn’t need to do much artful, careful cropping!  If you’re wondering about how the photo packages work,  the crew member takes photos and video from the moment before lift-out until you return. You can purchase these for $45 and if you have an iPhone, they are transferred right on the boat. You can also get the memory card with your images. You will need to edit since you get the untouched photos straight from the camera.

Would I Go Parasailing Again?

Yes! Not right away but I’ll definitely look into parasailing experiences for future trips.


4 Comments Add yours

  1. sounds like an amazing experience. i’ve always had irrational fears of being repeatedly dipped into shark infested waters 🦈 Something I may have to conquer.


  2. I’m glad you had a wonderful experience parasailing! I’ve been once with a friend, so I didn’t have to do the whole stranger small talk thing, haha. I agree that it was an amazing experience. So much fun! Scary at first, but goes away in an instant.


  3. Looks like fun! Makes we wonder if Parasailing still goes on here back home in Barbados! Also cheers to 30.


    1. Natasha Beckles says:

      Thanks! I don’t know about it being done here though.


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