Key West Parasailing: Ideal For Cruise Ship & Downtown Guests

Me and my son did parasailing for the very first time and it was more that we could ever expect! My son is 10. The entire experience was exciting and just hard to describe-you have to try it!!! It was not scary at all, once up high in the air we felt like soaring birds looking over the peaceful ocean below. We asked to dip us in the water and it was so much fun! The landing was smooth and my son wanted to go again :) We got the picture/video package and it is totally worth getting because they are of professional quality and look beautiful. A big thumbs up!

Had such a fun time with Ian & Joey! Definitely will come back and do this again. Thanks guys!! You’re the best.

The trip was blast! If this is something you have always wanted to do and you’re a little to scared to do it just book the trip. You won’t regret it!

Absolutely a BLAST! Very professional! And the photos are a MUST to buy! Such great, professional pictures! This company and workers are hands down #1!

My first time parasailing and I had fun! The 2 crewmembers knew what they were doing and made everyone on board feel safe and secure. Actually, I don't really know if that's true but they made ME feel safe. As I was solo, they put me with another solo boatmate. You are up there for about 5 minutes or so, which is enough time for me.

This was an amazing experience! Captain Grant and Mate Canon were wonderful. They made everything seemless. They were funny, professional, and made the trip awesome! We highly recommend doing this at least once in your life!

Great experience. Logan and Joey made sure everything went flawless and made sure everyone was comfortable and had a great time.

Ian and Wyatt were absolutely amazing! Excellent with the safety speech and the photographs are absolutely amazing. Highly recommend that you request these two because they know how it's done.

Very professional and nice, they know exactly what they’re doing. Efficient at getting the riders up in the air, and have us a perfect amount of time in the air. Great photos (for an additional fee). I highly recommend them, I would definitely go back to them.

Our captain and the parasailing assistant were awesome!!! Great personalities. Very engaging with everyone on board. My husband parasailed and I rode on the boat. It was enjoyable and relaxing. I would recommend them to anyone.

Joey is awesome. He made the experience really fun! We were a bit scared but they made us feel safe. Try it out.

Had an excellent experience parasailing in Key West. Friendly crew & they took great care of us. One of the passengers on our tour had an unplanned water landing & the crew was very calm, reassuring, patient & handled the situation perfectly.

We had never been parasailing before and we are senior citizens. Login and Joey were our captain and crew chief. Both were professional, fun and so helpful. We would go with them again in a heartbeat 💜💜

Timely, courteous, safe, overall great experience. Logan and Joey were awesome hosts.

Worth the money. Was on my bucket list. So pretty to see the island from a different perspective. Highly recommended

The crew was very knowledgeable, educating, professional, friendly, they went beyond the call of duty to provide an exceptional experience. It nice to work with someone who loves what they do. I would love ❤️ to experience this again with this same crew they were all amazing. Thank you for hiring such great employees

Best parasailing trip we’ve ever done. Crew was super fun, and the flight was so amazing! Logan and cannon were amazing!

The crew was friendly and attentive, making sure we were comfortable with the experience. This was a wonderful way to spend an hour in Key West, and the views from the air were amazing! We wholeheartedly recommend this experience and crew!

We booked parasailing activity with Sunset water sports. Sean and Logan was our captain and photographer. We had a great experience and it was very safe. They asked us how wet do we want to get before going up to the air and it was a lot of fun. The weather was perfect and we got a little extra time to stay in the air. Highly recommend parasailing with Sunset water sports!!

This was my first time parasailing at 58, and Rachel and Logan were excellent. I went to their Smathers Beach location, which is a quiet beach good for families about 15 minutes by car from downtown. The experience was much smoother and more comfortable than I expected, and the sights and sensation of flying was incredible. I did the 5 pm departure, and got some amazing views of the sunset, including the fabled green flash! Logan’s pictures were awesome, so budget in $30 for all your digital photos.

Wyatt and Sean had excellent energy for this kind of activity. They were personable and attentive. The directions and procedures were very clear. We had The Best Time for our first parasail experience!! We were amazed at the views and how smoothly we went up and down! I highly recommend this experience and the crew!!!!!!

Amazing experience!! This was our First time to parasail!! They made it stress free and fun! Highly recommend . The water was so beautiful.

Do not book. Very rude, paid to change the time and they said it was not paid. I showed them where it had been taken out of my account, they said I must have purchased something else. I didn't.

Pros: good explanation of procedure, safety was foremost, and they kept me dry. Con: very difficult to find office, 45-minute wait from check-in to start was too much wasted time.

It is so much fun. I went with my 83 yr old mom and she loved it!! The boat was full but we felt safe. Very upbeat, they took pictures and did an awesome job. Great experience!

Wow, what an incredible experience. My partner and I had a blast and were so grateful to have received such great service. Our group laughed, whooped, and vibed to the captain's music. We were initially a bit nervous as this was our first time, but felt welcomed and safe throughout. We purchased the photo package, which included a video, and will cherish these memories forever.

First time parasailing. It was a blast. Wyatt and Taylor were great! The view was beautiful, I could have stayed up there for hours.

While the parasailing and captains were great, the rest leaves a lot to be desired. First we were sent to the wrong dock and the boat we were supposed to be on had to turn around and come back for us. Then I paid $60 for the picture package that was supposed to be sent to my phone and when I got back to the hotel they weren’t there. I called to just get my money back and felt blown off. Would recommend the staff on the boat but not much else!

We had a blast on our parasailing excursion today with sunset watersports. Tyler and Whyatt were the best; if your in key west, it's a must do! Highly recommend

So much FUN! Haven't gone parasailing in over 20 years and felt like a kid again! The crew was friendly, professional and made us feel at ease from start to finish. The views were breathtaking! It was the perfect mix of thrilling and peaceful. Highly recommend to anyone looking to add a little adventure to their Key West trip! Also--for an extra fee the crew will take photos of your flight. Totally worth it! We got some great shots!

Great trip with great guides - calm seas and beautiful water. I’d gone 20 years ago. My son was dying to go and loved it. Boat drivers Connor and David were excellent easy to talk to. Connor’s even gave us a great restaurant recommendation after we returned to dock.

Best experience on the island for me! This was a top 5 vacation experience overall! David took amazing pictures and the captain(can’t remember his name) was the best, definitely recommend this for anyone!

We couldn't have asked for a better experience. My husband is handicapped and they were so accommodating and made sure the experience was great for him. We saw a shark in the water below us from high in the air. So glad we booked this tour. It was one of the highlights of our trip to Key West.

We loved it! It was a thrilling first time adventure for us! The views were amazing and the feeling exhilarating. Tyler and Dave were an awesome team; they instructed us well and we felt safe at all times. We highly recommend parasailing with Tyler & Dave!

Very fun and the crew is helpful and fun. Equipment looks well taken care of and the view is amazing.

The whole experience was amazing, we took a lot of pictures. staff was awesome, activities were fun and the food was great too. definitely planning another trip.

Captain Rachel & Wyatt were amazing! This was our first time parasailing and they were incredibly patient and operated like a well oiled machine. We were incredibly grateful for the photos taken, and for a fair price as well. The entire experience was perfection and we’d absolutely do it again.

Wyatt and Rachel are an awesome TEAM!!! THEY BRING FUN!! It was for sure an experience i could do all day everyday!!! Go enjoy!

The guys were all super friendly and very safety oriented. Greatly enjoyed this not scary at all ;) lol

It was so easy and so much fun! Not scary at all, and the guys are great on the boat. I am so glad at age 65 that I did it and would feel comfortable in twenty years doing it again!

The views were amazing, Johnny was great captain and Rachel kept us entertained and ensured we had a good time. She took some awesome photos of our trip for us, highly recommend!

My family and I had an amazing parasail experience with Tyler, Rachel, and Logan at Sunset Watersports. Everyone from the check-in desk to boat crew were very friendly and accommodating. My daughter and I parasailed, and for a small fee my husband was able to join us on the boat. 10/10 experience, highly recommend.

I went parasailing with my teenage son. We booked the night before and had great weather. Amazing experience over the bay, riding out from downtown. They were running a discount during their 40th year. They offered a photo package too which gave us some great photos and video of our experience. We made some great memories and are so glad we did it when the opportunity arose.

The water was beautiful and all went smoothly with checking in and getting on the boat. The boat was running a little late, but we all still got our chance to parasail for what felt like a long time.

Expensive for 8 mins parasailing , staff in the boat demand additional photos package to buy else won’t you best experience . Very disappointed! Btw, we did tip them at the end as courtesy.

Para sailing has been on my bucket list & while vacationing with my daughter in Key West, I decided to check it off my list. I was very excited AND anxious, but I was determined to make it happen. The experience was more than I expected, & the captain & assistant were great. I definitely recommend it.

Great experiences both activities for myself and family. Trips were easy to book through hotel concierge. Location convenient, check in and boarding seamless. Friendly staff, great customer service on both boats. Whale watching trip included snorkeling…down side was we saw barely any fish but did see lots of whale activity on the way back. Best part of trip was the actual 40 minute boat trip…peaceful scenic beautiful water. Tried parasailing first time…captain and Wyatt gave great instructions…put us at ease. Knowledgeable and professional, we felt we were in good hands. Downside it was very short (10 minutes) but fabulous experience and the best part were the photos by Wyatt…perfect for memories. I would use this company again.

Best excursion on our trip! It was small, and the 2 guys running the boat have it down to a science! It was so fun!!

Sean and Matt were awesome. I bit cheesy but most people love that kind of stuff. Felt a little motion sickness with all the turns but I grew up on a boat so that comes with the territory.