Parasailing over the Historic Key West Seaport

This was our first time parasailing and we had a blast! Crew made us feel safe and even took some great pictures of us!

My husband and I went on the parasailing trip with Sunset Watersports on 08/12/2026 at 9-10am and we had an unforgettable experience! I believe we were with Captain Rachel and Brody, and they were great! The views from above are incredible!

The tour guides were incredible!!! Book straight through sunset watersports. I will definitely go again.

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!

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 🤞🏾✊🏾🖤💋

Great experience with Sunset parasailing. Great captain and crew. Everyone in our group loved the experience.

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.

Joey and Tony (I believe was the other guy) were amazing. We had an amazing time with them. Recommend 100%