Sunset Watersports

We had no plans to rent chairs and an umbrella, but this place became our life saver instantly when we realized immediately how badly we needed one. The price seems a bit steep at first but after spending hours on the beach on a hot day, it’s worth every penny. The guys working were incredibly laid back and polite to us and helped us get everything set up so we could enjoy our day. Later in the day, we stopped by again briefly to grab a few waters and snacks to cool us down. Even though we only rented the chairs and umbrella, they also offer plenty of other beach add ons if you were interested. Very friendly, helpful, and convenient. I recommend taking advantage of this place when you go enjoy a beach day.

We were on vacation in January 2019 and came to Key West. We purchased the tandum parasailing for $85 online. It was one of the best experiences of my life! My husband and I have been waiting to parasail for a long time and this was so amazing! It was so peaceful when we were sailing in the sky. The staff were very friendly, and you can pay an extra $45 for photos. The photos taken by the staff were great, and they even gave us a video of us being lowered into the water. Please note, the parasailing booth is on the other end of the beach where the boat is docked, not at this location. (Sunset Watersports have two huts!)

We had a great experience with sunset water sports at Smathers beach. Kayak,, paddle board, and sailboat rentals were included with our hotel stay across the street. They had plenty of equipment available, the employees were friendly, and it was a very simple process. Would recommend.

Had the best time with Sunset Watersports! The crew is always helpful and fun.

Highly recommend!!!! Sunset Watersports crew was amazing, the equipment was brand new and the price was lower than anyone on the island. We had a blast and would highly recommend this company to everyone.

This is by far the most fun l could have had with my daughter for our entire trip. They treated us like family and also made sure we ate as well as were on time for our watersports. Parasailing by far with this crew was the best lve ever experienced anywhere in the United States. Special shout out to Captain Sarah for being the coolest most informative person l met in Key West as well as down to earth. Captain Clay was funny, informative, and very witty as well as an amazing Captain of the Party Cat. Bartender Alex was fast with drinks and makes an amazing sex on the beach as well. She was also very friendly and treated my daughter as family. The virgin daiquiris were on point btw just saying. Lunch was definitely a treat with the best boat food Ive ever had as well. The pulled pork sandwich is absolutely the best ever. If l could give 10 stars this place earned every single one to be honest. Btw the captains all were amazing not to take away from anyone these few just stuck out to me and made my whole trip amazing. In closing if you get a chance to go theres an amazing ship wreck there you can snorkel around absolutely worth your time to paddleboard or kayak too. Absolutely will be doing this again.

Captain Steve was great, knows the keys very well. Thanks Captain

Had a great time parasailing was awesome and the staff was helpful and friendly

Purchased a day pass on Expedia included all rentals and a parasail ride very clean beach

Terrible and disappointing experience with this company. We booked Beach Pass with Parasailing at Smathers Beach by Sunset Watersports through Tripshock. We went to the beach in the morning at 8:30 am, as required by the company. The booth was closed. No one was there.That’s not the worst part. The whole area smelt like the restroom is broken and stools are floating in the air. The water was brown, and seaweed everywhere. Nobody was there. You don’t want to let the water touch your skin, let alone swimming there. As you can see from the photo.We contacted the booking agency Tripshock. They said they don’t have the power to cancel the reservation, only the Sunset Watersports has to say yes.Then I contacted Sunset Watersports to cancel the trip. Horrible customer service began. She had a very bad temple. She kept insisting that whether customers have good or bad experience is not their responsibility, has nothing to do with them. And she said, wait, let me give you a number to call. Then making us wait several minutes, she gave us the city’s number, sardonically said you should go call the city to complain.And when asking about if we can refund, she repeated resentfully, “I don’t have the money! The booking agent has your money! Call them!”Several calls went back and force with both of them. The sunset watersports and the Tripshock kept passing the buck. And we still did not get any feedback from either of them till today.Then when we talked to locals, they said that the beach was smelly for two months. Sunset Watersports is right on the beach. How could it keep promoting this beach package, and not mention this situation at all? It has no consideration for innocent visitors who live far and have no idea of this situation. How could visitors from elsewhere know the beach smell when booking the trip thousands mile away.Just be aware of this company’s terrible customer service and this terrible package.There are a lot of other good companies, avoid this Sunset Watersports. We wasted the whole morning for our three days trip in Key West. Gladly, we cut our loss and booked another parasailing trip with Sebago Watersports on the other side of the island, near Key West Bight. They provided us a very positive experience.Hope you all know about this situation before booking your trip with this company. Vacation should not be wasted on things like this.

Parasailing with Ian and Matt was amazing. They were awesome and made the trip worthwhile. 1st time parasailors and they made us feel confident with their expertise. The dip was the best part!

Super friendly and helpful staff! Jake, Jesse, and Devin assured everyone had a blast during our trip around the island on jet skis.

We had THE BEST time!! Parasailing at Smathers in Key West was a honeymoon highlight! Definitely use their service! Easy to schedule! You can see from one side of the key to the other!

Do NOT waste your time or money on sunset cruise. Bad watered down drinks. All you do is drive out and sit. If you are on the wrong side if boat you see nothing but everyone elses head. Crowded with loud drunks spilling drinks on you. Stay on land and go to Mallory square. Same view and cheaper.

Great tour guides! Had a blast with them. Will definitely be coming back next time I’m in town.

Rented a boat in late November. Upon arrival the boat we ended up with want anything like the 1s in advertisement. The boat we were sent out on was old and quit running a little over an hour into a 4 hour lease. Could not get anyone to comment, they said they would call manager and take care of in the next day. I called 4 times before leaving the Keys to go home. No one was ever available that said they could do the refund. NOW I RECEIVED MY CREDIT CARD STATEMENT AND THE LEASE FEE AND DEPOSIT WERE BOTH STILL ON AS A CHARGE! Not only did we waist a half day and then be CHARGED FOR FAULTY EQUIPMENT. TRIED TO CALL BEFORE WRITING THIS, AGAIN NO ONE AVAILABLE!

Called last week for a windsurf rental. Took Uber to Smathers beach to be told they didnt have a windsurfer.Uber back to cruise ship . Uber costs 45 dollars. No windsurfer plus dragged my wife on this fruitless effort. Captain tried, but day was a bust. ALWAYS PHONE

Best one in town.

Great staff! Funny, engaging, and knowledgeable! Had Gavin and Scott! Great time in the open water.. Hooked up by Kevin at Smathers beach!!

Offers great water adventures at Key West. Reasonable prices for fun adventures.

Great, easy going, on-beach rentals.2019 update: except on the days when they dont show up at all. No explanations, no excuses, no promises to send someone to open the stand even after you call them. Just locked up and out of commission on a nice day :-(

Dont buy photographs not worth $45. Other than that had real fun parasailing.

Took this on the day after labor day and I was overjoyed with all they offered. Great staff and a great time

Asking for 15-20% tip for little to no service. Aren’t two chairs and umbrella for $45 bucks enough.

No discounts for Veterans, even though they claim they give them to get you there.

Awesome experience! Tyler was great and took awesome photos for us!!!!! Must do experience in Key West

One word:FABULOUS!!!Do not miss this opportunity to see and feel the exhilarating views of Key West and the surrounding waters.Nick and Andrew at Sunset Parasailing are smart, helpful, thoughtful, and terrific!This was the first time ever that my husband and I had parasailed!Perfect experience

Great experience, 10/10 parasailing. Great crew, they really know what theyre doing and are masterful hosts. Cant wait to experience this again! Hopefully my mom doesnt make a scene for no reason next time, bc I, as the parasailer had a transcendental experience.

Ive rented the small hobie cats (small sailboats) here before and the prices were always a bit ridiculous for what youre getting. But now theyve gone up to $50-$70 PER HOUR. So you can get an all day beach pass from them for $79 which includes unlimited sailboat rentals for the entire day AND a parasail ride. But if you dont have time/want to deal with that and just want to walk down to the beach and sail around for 90 minutes its $140. What sense does that make?Probably why you only see someone using the cats once in a blue moon.

Check out the beach pass if you want to spend a relaxing day on the island! Relax at your own pace on beautiful smathers beach and enjoy all the activities they have to offer! take a parasail ride, and then go try out the hobie cats, or go for a cruise on the paddleboard! awesome crew! totally recommended.

Friendly crew. Nice parasail ride.Picture package was worth it.The music on the boat was a bit too loud when on the boat, but then its made to be heard when parasailing as well.Many thanls to the team.Experience not to be missed while in Key West!

Awesome experience, great crew, very reasonably priced! I recommend the photo package!

Amazing people, great service. Enjoyed to the fullest. Very enjoyable.

I love it I love anything in Florida

Awesome time

Fun times!

These guys were awesome, skilled and took our photos too

Solid operation