Parasailing over the Historic Key West Seaport
Recommended by 90% of travelers
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 travelers with back problems
- Not recommended for pregnant travelers
- No heart problems or other serious medical conditions
- Most travelers can participate
- This tour/activity will have a maximum of 12 travelers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
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!
Reviews
4.7
based on 238 reviews
Sort by: Most insightful
The tour guides were incredible!!! Book straight through sunset watersports. I will definitely go again.
Response from Host, Aug 2026
Thank you so much for the fantastic review! We’re thrilled to hear that our tour guides made your parasailing experience incredible. We truly appreciate your recommendation to book directly with Sunset Watersports, and we can’t wait to have you back in the air for another unforgettable Key West adventure! 🌴🪂🌊
Joey and Logan were amazing! It was our first time parasailing and they made it so easy and fun! We made memories that will last a lifetime!
Response from Host, Aug 2026
Thank you so much for the wonderful review! We’re thrilled to hear that Joey and Logan made your first parasailing experience so easy, fun, and memorable. We love helping guests create those once-in-a-lifetime memories, and we’re so glad you enjoyed your adventure with us! We hope to see you back in Key West for another exciting experience! 🪂🌴🌊
There were two guys but i only remember one’s name and it was Ian. They gave me the best experience ever. Safety precautions were mentioned with professionalism but they were so down to earth. I love the way they made us feel comfortable…the whole group at that. Thanks guys 🤞🏾✊🏾🖤💋
Response from Host, Aug 2026
Thank you so much for your amazing review! We're thrilled to hear you had the best experience parasailing with us. Ian and the rest of the crew will be so happy to know they made everyone feel comfortable while maintaining a professional focus on safety. Creating a fun, relaxed, and memorable experience is exactly what we strive for, and we're glad they delivered. Thank you for choosing Sunset Watersports, and we hope to welcome you back for another unforgettable flight over Key West!
The parasailing itself was exactly what I hoped it would be, and that is where the three stars come from. Unfortunately, the overall experience surrounding it left a lot to be desired. I booked through Viator for an excursion with Sunset Watersports and received a text confirmation from Sunset Watersports directing us to check in at their Key West location. After checking in, we were sent to meet the boat outside Hammerhead Surf Shop. From that point forward, unlike the other Sunset Watersports excursion I had been on, nothing identified the excursion as being affiliated with Sunset Watersports, not the boat, clothing, or anything else. Our 'captain' was Rachel, with Brody assisting. From the beginning, I did not find Rachel particularly welcoming or friendly. I felt more like an inconvenience than a guest. She barely interacted with anyone and essentially introduced Brody by telling us he would take care of us. Brody, on the other hand, was friendly and made an effort. I mentioned that it was my daughter’s 21st birthday and asked him to please make sure he got some great pictures. When he helped her into the parasailing gear, he wished her a happy birthday and made an effort to acknowledge the occasion, which I appreciated.
We were told that Brody would take “amazing pictures” that could be uploaded to our phones for $60. Neither of them mentioned that they could take photos or videos using our own phones, so I did not think that was even an option. In fact, my daughter ended up taking photos and videos of another passenger’s parasailing experience with that guest’s phone. It was not until everyone had finished parasailing that Rachel even made much of an effort addressing the group, asking whether everyone had a great time. That was followed by a canned speech about tipping I'd heard from another excursion almost verbatim and how they did not want to have to get “real jobs,” along with comparisons to servers and bartenders who rely on tips. She also commented that if she made us feel safe, we should make sure she received a good tip. I understand completely that many tourist excursions are tip-driven, and I am happy to tip well for great service. However, making passengers feel safe should be a basic expectation when you are the captain responsible for taking people parasailing, not something presented as a reason for earning a tip. Tips are earned through the overall service and experience, and even a small amount of genuine interaction and friendliness throughout the trip would have made a significant difference.
As we returned to the dock, we were again reminded that the photo package was $60 and that cash was preferred, if possible. The repeated focus on tips and additional purchases stood out even more because there had been so little effort to engage with us as guests during the actual excursion.
As we were being quickly moved off the boat, I heard Rachel tell someone waiting for the next excursion to “sign the clipboard and get on the boat.” Unfortunately, that summed up the experience for me: get them in, get them out, and move on to the next group.
The parasailing itself was great, and I am glad we did it. Brody was also friendly and made an effort, particularly after learning it was my daughter’s birthday. But an excursion like this is about the entire experience, not just the few minutes spent in the air. In a destination with so many companies offering similar excursions, customer service and personality are what separate one experience from another. For us, those things were missing, and the heavy emphasis on tipping without the corresponding level of hospitality made the experience feel more transactional than memorable.
Uncomfortable experience. I was the only black person in my group and the host kind of made it obvious by not interacting with me as much as all the other people(white) on the boat.
Great time! Staff was great. People are friendly. Place was very easy to find with no issues getting there from stock island.
Response from Host, Jul 2026
Thank you for your wonderful review! We're so glad you had a great time parasailing with us. It's great to hear that our staff was friendly, the location was easy to find, and your trip from Stock Island was hassle-free. We appreciate you choosing Sunset Watersports and hope to welcome you back for another adventure the next time you're in Key West!
Joey and Tony (I believe was the other guy) were amazing. We had an amazing time with them. Recommend 100%
Response from Host, Jul 2026
Thank you for your amazing review! We're thrilled to hear you had such a great time parasailing with Joey and Tony. We'll be sure to share your kind words with them—they'll be happy to know they helped make your experience so memorable. Thank you for the 100% recommendation, and we hope to see you again for another adventure in Key West!
Very nice and knowledgeable would highly recommend! Felt very safe and he too great pictures. Had a wonderful time!
Response from Host, Jul 2026
Thank you so much for your kind words and recommendation! It was a pleasure having you, and I'm so glad you felt safe and had a wonderful time. I'm happy you enjoyed the photos, too! I truly appreciate your support and hope to welcome you back for another adventure in the future.
Everyone was polite and encouraging as a first timer. Highly appreciated their patience and encouragement. Had a great experience!!
Response from Host, Jul 2026
Thank you for your wonderful review! We're delighted to hear you had a great first-time parasailing experience. Our crew loves helping first-time flyers feel comfortable and confident, so we're glad their patience and encouragement made such a positive impression. Thank you for choosing Sunset Watersports, and we hope to see you again for another unforgettable adventure in Key West!
Wyatt and Logan did a great job taking care of us and all the passengers. They made it fun and enjoyable.
Response from Host, Jul 2026
Thank you for your wonderful review! We're so glad to hear Wyatt and Logan took great care of you and helped make your parasailing experience fun and enjoyable. We’ll be sure to share your kind words with them! Thank you for choosing Sunset Watersports, and we hope to welcome you back for another adventure in Key West soon!
Ian and Wyatt were very professional and made the whole parasailing experience a fun event for the whole family. Wyatt’s photos turned out great. Absolutely recommend.
Response from Host, Jun 2026
Thank you for the wonderful review! We're thrilled to hear that Ian and Wyatt made your parasailing adventure fun, safe, and memorable for the whole family. We'll be sure to pass along your kind words to them. We're also glad you loved the photos Wyatt captured—they're a great way to relive the experience! Thank you for recommending us, and we hope to see you again on your next visit to Key West. 🌴🪂😊
It was a great time and experience. The crew was excellent and explained everything thoroughly. I would do it again.
Response from Host, Jun 2026
Thank you for the great review! We're thrilled to hear you had such a fun parasailing experience with us. Our crew takes pride in making sure everyone feels comfortable, informed, and ready to enjoy the adventure, so we're glad their efforts made a difference. We truly appreciate your kind words and are delighted to hear you'd do it again. We look forward to flying with you on your next trip to Key West! 🌊☀️🪂
Joe and Ian were great! Nice clean boat and Jose took great pics while parasailing. Highly recommend l!
Response from Host, May 2026
Thank you for the fantastic 5-star review! We’re so happy to hear you had a great parasailing experience with Joe, Ian, and Jose. Our crew works hard to provide a fun, safe, and memorable adventure, and we’re glad you enjoyed the clean boat and the awesome photos from your flight. We truly appreciate the recommendation and hope to see you back in Key West for another adventure soon!
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.
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!
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!
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!
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!
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!
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!
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.
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!
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! 🌊
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.
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.
Both were Amazinggg. Would definitely recommend to everyone. The pictures came out amazing. The energy and music was a plus.
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.
Wyatt and his first mate (forgot his name) were great and the pictures they took made a great memory
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!
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
From $64.45
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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