Parasailing over the Historic Key West Seaport
Recommended by 90% of travellers
Badge of Excellence
Key West, USA
- 1 hour (approx.)
- Mobile ticket
- Offered in: English
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Overview
Try something new in Key West: parasailing. Adventure seekers who've booked this trip will love soaring over the Key West Seaport. The experience is available for singles, doubles, and even triples so it's a fantastic activity for a group of friends or a family. You'll board a state-of-the-art boat, get briefed by the crew, and then fly over the city—free as a bird.
- Invigorating parasailing experience over Key West Seaport
- This activity is available for singles, doubles, and triples
- Convenient departure point at Sunset Watersports booth at the port
- Multiple tour times so you can easily add this activity to your schedule
What's Included
- Parasail Ride
- Gratuities
- Professional photo package of the experience available for purchase
Meeting and Pickup
Meeting point
- 201 William St, Key West, FL 33040, USA
End point
This activity ends back at the meeting point.What To Expect
1
Sunset Watersports
2
Key West Historic Seaport
3
Florida Keys National Marine Sanctuary
Additional Info
- Confirmation will be received within 48 hours of booking, subject to availability
- Not wheelchair accessible
- Not recommended for travellers with back problems
- Not recommended for pregnant travellers
- No heart problems or other serious medical conditions
- Most travellers can participate
- This tour/activity will have a maximum of 12 travellers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveller Photos
Featured review
Tiffany_G
Highly recommend booking with this company. The two men that helped us were professional and fun! They also offer a picture package.
Reviews
4.7
based on 222 reviews
kristenotankis, May 2026
The captain had a wonderful playlist, the ocean was beautiful and parasailing was great! About an 1hr total on the boat and 4 groups parasailed. Very safe, friendly and professional!
Response from Host, May 2026
So happy to hear that you enjoyed your time with us. Thank you so much for the 5 star review.
Cynthia_C, Apr 2026
Logan and Joe were fantastic, had a great time and lots of laughter both on the boat and up in the air. They’re worth every dollar and more! Definitely a great experience. We got the photos as well and Joe got great shots. Happy we did this on our first day in Key West!
Response from Host, May 2026
Thank you for the fantastic review! We’re so glad you had such a great time with Logan and Joe they’ll love the shoutout. It’s awesome to hear you enjoyed the laughs, the experience, and the photos too! Starting your Key West trip, this way is the perfect choice. Hope to see you again!
Tiffany_G, Apr 2026
Highly recommend booking with this company. The two men that helped us were professional and fun! They also offer a picture package.
Response from Host, Apr 2026
Thank you for the recommendation! We’re glad our crew made your experience both fun and professional. Hope you love the photos and come back again soon!
Andrea_M, Apr 2026
The captain and photographer were fantastic even got my hubby up there he is scared of heights. Highly recommend to first timers
Response from Host, Apr 2026
Thank you so much! We’re thrilled to hear the captain and photographer made your experience great—and especially that your husband felt comfortable enough to give it a try! We really appreciate the recommendation and hope to see you again soon!
Meaghan_O, Apr 2026
The two Logans were great and patient. They were knowledgeable and fun. Made my kids feel safe and want to do it again!
Response from Host, Apr 2026
Thank you for your wonderful review! We're so happy to hear that the two Logans made such a positive impression and helped your kids feel safe and excited about parasailing. Creating a fun and comfortable experience for families is what we strive for. We’ll be sure to pass along your kind words to them—they’ll love hearing it! We hope to see you all again for another adventure soon!
Karis_C, Apr 2026
Sunset Watersports was a great company to deal with. It was a great experience over all. Would definitely recommend!
Response from Host, Apr 2026
Thank you so much for your kind words! We’re delighted to hear you had a great experience with Sunset Watersports from start to finish. Your recommendation truly means a lot to us. We hope to have the pleasure of welcoming you back again soon for another amazing adventure!
Joy_B, Mar 2026
Logan and Wyatt took care of us from start to finish- explained the entire process and made us all really comfortable - Logan’s music choice were great!
Response from Host, Mar 2026
Thank you for the kind words! We’re so glad Logan and Wyatt took great care of you and made you feel comfortable throughout the trip. We’ll be sure to pass along the compliment on Logan’s music too! Hope to see you again soon!
Tracie_S, Mar 2026
Mixed Experience - guys were nice enough.
Music was ridiculously loud. Love turned up music, but there is a limit.
The mate was more interested in selling us pictures and taking pictures during the trip; he was running around like a chicken with his head cut off the entire time, taking pictures and trying to manage everything else. I bent down to put stuff under the seat and smacked me in the nose and didn't even realize it. I think he should focus on the safety of what is going on.
And they went around in pretty tight circles with the boat ride, they didn't go straight much - different than other experiences parasailing - a little sickening for the wife.
It was beautiful out, and everything was safe, but if something went wrong, there were plenty of distractions to divert their attention.
Also, they told us to arrive 45 minutes early, and then at check-in they were like, "Why are u here so early?" And then we had to sign more paperwork on the boat after being so early. And while we waited, there were no benches on the dock to sit, when they told u to get there 45 minutes early.
Debra_K, Feb 2026
Wade & Ian were absolutely the best to get the most out of your time up above! It was super..needs more than 5 stars!! Lived the music! They got everyone excited and relaxed when it came thier turn..had 7 couples 9n the boat and No One backed out ! DEFINITELY will book with guys we also booked the sandbags excursion..Deb & Keith (my oldest son side kick)
Absolutely give
Sunset water sport a try..Best Around!! Deb
Response from Host, Feb 2026
Thank you so much for the incredible review, Deb!
We’re thrilled Wade and Ian made your time “up above” so much fun and kept everyone excited and relaxed. We’ll be sure to share your kind words with them.
Thank you for booking the sandbar excursion too, and for recommending Sunset Watersports as the best around — that means everything to us. We can’t wait to welcome you and Keith back again soon!
Felice_R, Jan 2026
It’s a lot of fun and anyone can do it! Ian and Joey were great and the photos they took were priceless
Response from Host, Jan 2026
Thank you for the great review! We’re so happy you had such a fun time and that Ian and Joey made it extra special — and we love that the photos were priceless! 😊📸 Hope to see you again soon! 🌊
Yuxuan_Z, Jan 2026
It was a fantastic experience, and I would absolutely recommend it to friends visiting Key West, FL. :)
Response from Host, Jan 2026
Hi Yuxuan, thank you so much for sharing your great experience, we hope to see you on your next adventure.
Glenn_C, Jan 2026
Take the trip even if you are afraid of heights! Everything about the trip was FUN!! The boat ride was fun! The guys were fun! The parasailing was fun! And the music was fun!! You won’t regret it!!
Response from Host, Jan 2026
Hi Glenn, sounds like you had a blast, we appreciate your five-star review.
Timothy_P, Jan 2026
Both were Amazinggg. Would definitely recommend to everyone. The pictures came out amazing. The energy and music was a plus.
Tammy_T, Dec 2025
My Hunny and I booked for a10am morning parasailing adventure. His first time, and a little afraid of heights, I have a “flying every chance I get” bug 😁
We went out on a perfect day for parasailing.. little breeze, warm enough outside. The 2 guy crew couldn’t have done more to bake everyone on the boat feel comfortable and safe and have a great time. We bought the photo package and they turned out fantastic!
My hunny said he couldn’t believe how much he enjoyed it- so peaceful.
Will be coming back to sunset again when we come back to KW.
Amy_R, Dec 2025
Wyatt and his first mate (forgot his name) were great and the pictures they took made a great memory
Lesley_A, Dec 2025
We had such a fun time! Joseph and Ian know what they are doing. There were 12 people on the boat, it ran to time and everyone got a good amount of time parasailing (around 8 mins each). Highly recommend!
karamuking02, Nov 2025
I don’t know how to swim, however you don’t need to know how to swim…. Grateful experience!
I will definitely try it again
Christopher_W, Nov 2025
They open at 8 and the pricing is different for different times.
The Logan’s were great. They explained how the flights would work and asked if we wanted to touch the water. It was such a neat experience and we would love to do it again.
We heartily recommend this experience!
Thomas_C, Nov 2025
Our entire excursion, from booking to finding our location to begin our adventure to the parasailing itself was effortless and truly made our vacation. Tyler and Rachel were just the best! Very professional, personable, and gave clear instructions. A great time from start to finish.
Response from Host, Dec 2025
Thank you for the wonderful review! We’re thrilled to hear everything from booking to takeoff was smooth and memorable. Tyler and Rachel will be so happy to know they made your parasailing experience exceptional. We’re glad it was a highlight of your vacation and hope to see you again soon!
michelle_m, Nov 2025
Great adventure. Wyatt and ian were fantastic guides and made our experience even better. Got to see the entire island.
Response from Host, Nov 2025
Hi there,
Thank you so much for sharing your experience with us!
We’re thrilled to hear you had a great adventure and that Wyatt and Ian helped make your trip even better. It’s wonderful that you were able to see the entire island — what an unforgettable way to explore!
We truly appreciate you joining us and hope to welcome you back again soon.
Lauren_F, Nov 2025
Had the best time! Logan was ace and had a fabulous playlist too! The guy taking the pics was also lovely! Possibly Kenny?
Would recommend to anyone!
Yolanda_T, Oct 2025
We had the best experience Parasailing in Key West. The Parasailing guides were very kind and helpful and even went back to pick up a hat that fell in the water. The experience itself was amazing, Parasailing over beautiful blue water and enjoying the views. Overall it was a very pleasant experience and would recommend.
Response from Host, Oct 2025
thank you so much for the 5 star review Yolanda. we really appreciate your feedback.
Joy_N, Sept 2025
We felt very safe with Shaun and Logan
They were very friendly and professional and took great care to make sure we felt comfortable, especially the first timers in our group.
Response from Host, Oct 2025
Thank you for sharing your experience! 🌊 We’re so glad Shaun and Logan made you feel safe, comfortable, and well taken care of — especially for the first-timers in your group. They’ll be thrilled to hear your kind words, and we hope to welcome you all back for another great adventure soon!
Nathaniel_C, Sept 2025
The wife and I had a blast with Capt Ian and Wyatt today. Both were very professional and thorough with ensuring we had fun while prioritizing safety. Wyatt also took incredible pics of our experience. Highly recommended. Thank you guys!!
Response from Host, Sept 2025
Thanks a bunch for the great 5 star review, we're so glad you enjoyed your experience with us. Come back anytime we'd love to see you again!
Katie_N, Sept 2025
We first parasailed with Sunset Watersports 10 years ago and had a fantastic time. So much so that I remembered the name of the business a decade later. When we returned to Key West with our kids, I made sure we were booked with the same company. Logan & Logan were awesome, and the experience did not disappoint! The guys were fun, super friendly, funny, knowledgeable, and safe. They did a great job with photos again. The kids had a blast, and we did too. We may not visit often, but they’ve got a family of customers for life. Thanks Sunset Watersports - you’ve still got it!
Response from Host, Sept 2025
Hi Katie, I want to thank you for your amazing review and sharing your great experience. We really hope to keep building great memories for you and your family, see you on your next visit.
Noy_V, Sept 2025
It was my first time doing parasailing, had great time and experience. Right from the get go Logan and Logan were awesome and knowledgeable. Very friendly!
Response from Host, Sept 2025
Thanks for sharing your first parasailing experience with us! We're glad you had a great time Logan and Logan will be thrilled to hear your kind words!
Elena_D, Aug 2025
We had a great time. The guys were amazing., very knowledgeable as well. Made us feel safe and entertained.
Response from Host, Aug 2025
Hi Elena, thank you for sharing your experience, safety is one of the most important things, hope to assist you again soon.
Andy_M, Aug 2025
The experience of gliding in the air was peaceful and beautiful. Our guides, Wyatt and Tyler, were phenomenal. We felt safe and they made the entire experience a lot of fun. Don’t miss this!
Response from Host, Aug 2025
Thank you so much for the 5 star review! We are so happy to hear that you enjoyed your time with us.
Jacqueline_C, Jul 2025
Conner and Joey were amazing. Had 2 terrified of going. They made it easy and was so much fun. Highly recommend!!
Response from Host, Jul 2025
Thank you! We’re glad Conner and Joey made it fun and easy for everyone. Appreciate the recommendation!
Monica_U, Jul 2025
Had a great experience. Tyler was incredibly friendly, helpful and accommodating before, during and after our excursion. His partner took pics f us all flying and downloaded them all on our phones. Highly recommend!
Response from Host, Jul 2025
Thanks for the kind words! Tyler and his partner will be happy to hear this. We appreciate your recommendation!
From US$59.95
per personup to 24 hours before the experience starts (local time)
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Parasailing over the Historic Key West Seaport
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