1. Parawest Parasailing Key West

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Key West, FL

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Parawest Parasailing Key West

4.5 (57 reviews)
Closed • 9:00 am - 7:00 pm

Parawest Parasailing Key West Photos

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After my parasailing adventure with Parawest.
Kory A.

For only $35 they let you fly, or "sail" for eight to twelve minutes. When I arrived the crew were friendly and relaxed. They provided some simple instruction, but it all seemed too easy to be true. Then, I watched the couple ahead of me go first. They were going to fly together. As I watched them shoot off into the air, I was worried I made a mistake. It looked scary. What if you fall into the water, or worse, what if you get disconnected and sail off into the island? A thousand other possible scenarios ran through my mind. When they returned, the guests looked happy. They crew told me to stick on the harness and walk to the top of the boat landing. In less than 60 seconds (literally), I was up on the landing and he was saying "goodbye!" It was so effortless and relaxing -- complete opposite of what I expected. The take-off was so gentle, as was the ascent into the air. When you reached the peak, you just floated there like a cloud. It was so easy, in fact, that I had my hands off the harness in no time to take pictures and wave to the video camera. The crew members said I could flip myself upside down, but I opted to save that for next time -- I have to have something to look forward to, right!? As I soared, I witness a breathtaking view of Key West from overhead. I watched sail boats travel by, as well as big cruise ships. Jet skiers zoomed off in the distance. I also had the distant company of other parasailers who provided some color burst in the skyline. From the air, you could see the beautiful green and blue water, as well as sand bars and the coral reefs. Before I returned to the boat, the crew dipped my feet in the water several times. They then reeled me in for a smooth landing. For a small fee, the crew filmed my entire journey, and took still photographs. Check out the footage below. If you ever are in Key West, this is definitely an activity to try! I can't wait to try it again.

Angela Z.

Our parasailing is just by accident. When we were at the most southern pointe, I called them and Linda answered the phone with a cheerful voice! This is a good sign! The ticket is 60 dollars per person. There was a slight wait but when we saw the ship, we were relieved. Two handsome boys were helping people getting off the boat. Another good sign, right? The sail was beautiful! The colorful key west coastal waters dotted with colorful parachutes. We ordered the go pro package which was at a holiday special for 60 dollars. The took off and the sail was memorable! We absolutely enjoyed it! Great activity and cheerful crew! Highly recommend this place since we need to keep Chris with this fun job instead of a real world one where dog eats dog. Here all he needs to be aware of is the sharks. Happy new year!

Erica H.

Had an absolutely wonderful time parasailing! Chad was great and very fun to go with. Made sure we were all comfortable and asked what we wanted. I highly recommend going and having the experience! Absolutely beautiful and one of a kind experience.

Mady L.

Had a great experience! I love that it is privately owned and operated. there were only 4 other people on the boat with us which was great! we asked to be dunked and it was super fun! at first we didn't want to get the CD with pictures but I am glad we did because they came out wonderful, great quality pictures, worth the money!

Amit M.

Great fun activity good for about an hour or so on a day with nice weather. The staff is fun and friendly.

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8 years ago

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16 years ago

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10 years ago

This is hands down the best outfit on the island - my husband and I are locals and we would recommend this experience to anyone

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7 years ago

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Ask the Community - Parawest Parasailing Key West

Review Highlights - Parawest Parasailing Key West

“You are also given the option when you get on board to buy a photo package, GoPro package, or a combo.”

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Barefoot Billy's - Dolphin, swimming

Barefoot Billy's

4.7(580 reviews)
1.2 mi

An Amazing First Jet Ski Experience! I had such a fantastic…read moretime on the jet ski tour with Barefoot Billy's Watersports at Casa Marina! From start to finish, everything was incredibly well organized and professional. Mike in the office was so helpful and made the check-in process smooth and easy. Our guides, Tyler and Juan, were absolutely fabulous--friendly, knowledgeable, and made sure everyone felt confident and safe before we hit the water. This was my very first time on a jet ski, and thanks to their clear instructions and encouragement, I felt totally comfortable and ready to go. The tour itself was stunning--Key West is even more beautiful from the water! The weather was perfect, and I especially loved the calm, Gulf side, where we had some free time to go fast on our own. It was such a fun, memorable experience, and I can't recommend it enough. Thanks again to the team for an unforgettable adventure!

First, I want to say that Captain Jason and Bernie were great. They were friendly, professional,…read moreand did their best under the circumstances. My disappointment is not with the crew, but with the overall experience and how the tour was handled given the weather conditions. I had concerns that the weather would impact our excursion, so I actually called that morning to confirm the tour was still going as planned. I was assured we were going. Unfortunately, the tour was a complete disappointment. The main reason we booked was to experience the secluded sandbar, which is a major highlight of the advertised excursion. We never even made it to the sandbar. Instead, we barely snorkeled in rough waters that felt unsafe and certainly weren't enjoyable. We also didn't see the tropical fish, sea turtles, or other marine life highlighted in the tour description. The one bright spot was seeing dolphins, which we really enjoyed. However, that alone did not make up for everything else we missed. I completely understand that weather is unpredictable and safety comes first. However, if conditions weren't suitable to deliver the main experiences being advertised, I believe the company should have offered guests the option to reschedule or cancel rather than proceeding with a significantly reduced experience. Again, Captain Jason and Bernie were wonderful, and I don't fault them at all. But ultimately, we paid for an experience we simply did not receive. What was supposed to be a relaxing, memorable day on the water ended up feeling like a complete waste of money.

Photos
Barefoot Billy's - My friend and I - check out the sunset!

My friend and I - check out the sunset!

Barefoot Billy's - Besties!!!

Besties!!!

Barefoot Billy's - Hubby and sunset

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Hubby and sunset

Sunset Watersports

Sunset Watersports

4.4(20 reviews)
3.5 mi

Sunset Watersports took us out on a windy day. We got to our activities and before we could even…read moreget off the boat they cancelled our day. So ultimately we road the boat for 1 hour, getting sea sick, to do nothing. The crew was cussing saying they knew this would happen. When we got back to the docks, I requested to receive a refund, and free vouchers to come another time, because Sunsets poor decisions made it so our day was effectively wasted. There were no other watersports boats we could get on, and the rest of the weekend was supposed to be rainy. The front desk girl was EXTREMELY rude and acted as if my request was irrational. I had to call a manager who was also no help, it was even difficult to receive the refund. We eventually walked away sea sick and I had to wait nearly a week to get our money back, with our day ruined and the only opportunity for this sort of excursion gone. I made negative reviews on a couple sites to which I got defamatory responses back. Now, disregarding their poor behavior, manners, and morals, I wouldn't have ever considered Sunset had I know about their negligence lawsuit for the death of 2 parasailers which they were found liable for. Please consider Fury or another company, hopefully they'll treat you better and keep you safe.

This review is strictly for the crew on 10/4 for the do it all watersports…read more I came with my friends to celebrate my 30th birthday and we were a pretty large group- a group of 15. I chose to do the all watersports activity because I've done it many years ago with sebago watersports in 2018 with my family and our group of 20 people, so I was excited to go back with all my friends for my birthday and don't get me wrong we had a great time but it did feel very sales pitchy and a little chaotic. Let's start with the good: - great lunch - staff was nice - 2 different boats for parasailing -Cannon and Rachel for parasailing were great ! - jet skii instructor (not sure of his name, very cool guy), and he showed us a stingray -captain was amazing and very personable - small group on this day due to the weather which meant not so much downtime waiting for the next thing to do- which was amazing Now let's dive a little into the not so great: - we were forced to tip before getting on the boat about $15 per person which isn't crazy, but it does suck to be told you have to tip before even getting the service - our guide, not sure of her name but she was really nice but unfortunately really unorganized, we were told to split into two different groups since our group was quite large, which we did and while one group was off parasailing or jet skiing the other was left behind to utilize the banana boat & floaties, which were cool but we kept being told we were next for parasailing and to get ready, about 2-3x, which led to us getting out of the water and waiting for the boat that would come take us to go jet skiing or parasailing, but then kept getting pushed back until we were the last group to go. Thankfully we all got to partake in the activities but I can't imagine how chaotic it would've been if the boat had been at full capacity which is around 120 people versus on that day which was 30-45. I think it would've been nice to get an exact time within a 5-10 minute time frame to know when we should get back on the boat and wait for the smaller boat, as we had to get out of the water 2-3x just to be told the boat wasn't back or that we weren't next. - our friends who went parasailing first did not have a good experience with the crew and thought they were kind of rude Overall we all had a great experience, but I do wish they made some tweaks in organization and friendliness of some of the staff.

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Sunset Watersports
Sunset Watersports
Sunset Watersports

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Parawest Parasailing Key West - parasailing - Updated October 2026

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