Sunset Watersports

We’ve been parasailing many times in Key West. Sunset Watersports has THE BEST parasailing! We always take the boat by Smathers Beach for the great view. Ask for Ty or Miles and you will be guaranteed to have a great time. They have by far been our favorite Sunset crew members! Ty also took great pictures for us so be sure to ask about that. They are always well worth the money!

Did a jet ski tour. Reasonably priced, awesome friendly staff, and all around great time!

Very friendly staff and excellent tour guides. Jet skiis were fairly new and in excellent condition. Despite our group of 16 skiis, they managed to keep us all together while still allowing the faster of us to go full speed.
The 10am tour is
Usually available for $ 99/​ski for 1.5 hr tour around the island!

We loved Wednesday night sunset sip and Sail cruise $ 49 ea last week with appetizers and drinks included. Patricia who we checked in with was Ms. Cranky Pants did not appear to like the day or anything else. We really liked the staff on the boat. The singer! guitarist act, That guy was pretty good, though out of touch a bit for his target audience. This tour cruise was a highlight of Key West for us, since mainly we found the destination overhyped

Jake, Julien, and Curt are the shiznit! You won’t be disappointed. We did the 10am trip around the island and it was unforgettable. If you’re in Key West come check it out! If you’re not in Key West, get over here and check these guys out! We are here till Friday and probably gunna go out again. I dont know how you give these guys less than 5 stars. Jet ski ski ski ski!!!

we did the do it all… personally is just an experience that isn’t really comfortable for me but I did. I really enjoyed the Parasailing & I’m a little traumatic when it comes to water but I did it and very proud of it. Now a couple of things I didn’t like… was a little too much people on this trip I think… I have never done this kind of event before but I definitely think should it be a little bit better… I think the jet ski time was too little and the space to run around too… We did ended up doing 2 in 1 which is good I probably would it done it like that but wasn’t an option so I didn’t like that. apparently they didn’t have enough masks to do snorkeling and even though I didn’t want it to do that I found it a little bit uncomfortable that the guy from the sunset was calling the people back to get their masks. There was enough equipment in the boat for all the people that was actually interested in doing it. Just my opinion but if they just want to snorkel let them be. Over all I will do it all again but maybe with a coupon or something not with their full price.

Would give 0 if possible. Racist. Rude. Stay far away and give your business to Fury instead.

Thank you for the wonderful trip!!! Everything was perfectly arranged. Didn’t expect that they will receive so much pleasure. Staff were very helpful and attentive, the captain was at the height of the communication, with him was interesting. Passengers on the catamaran, we had 26 people, were all accommodating and we were very pleased to communicate with each other during the trip. After this trip I have decreased pain in the spine. Swimming in the ocean and a lot of mobility given their results. I highly recommend this trip for the whole family, couples and singles.

Took a 1 and ½ hour tour around the island with Jake «from State Farm» lol… had a blast and would recommend this tour to anyone :)

This is the worst water sports company I’ve ever seen! DON’T LET THEM RUIN YOUR TRIP!
My bf and I signed up for parasailing. The guys were not very welcoming, which was ok. Once everyone was on board, they told us they will be playing tricks and taking pictures when we are parasailing and will make a CD which we can buy later. I don’t believe anyone on the boat would expect it’s actually «Mandatory» to buy their CD when you get off and the CD would cost $ 40, which is more than the parasailing itself. After getting off the boat, I don’t believe anyone was interested in paying for the CD at least not for $ 40. Some people started telling the guys they don’t have cash so one of the guys followed those people to an ATM nearby. I think this is very creepy! Another girl said she only had credit card. The other guy who said «cash only» earlier took out a machine and said they’ll take credit card too. We told them we left everything in our hotel which is 5 min walk away and we’ll come back for the CD later. One of the guys looked mad. He said don’t you try to run away. We will find you! What kind of company is this? He was literally threatening us for something we did not agree to pay for. So no we did not go back and did not feel bad for it either.
That was the 2^nd time I went parasailing. My first time was in the Bahamas. The crew did the same tricks (like dipping you in the water, shaking the rope, etc.) to make parasailing more fun and they helped me take lots of nice pictures with my cellphone. They also reminded us to wear swimsuit because we’ll get wet. I had none of these with Sunset Watersports. I don’t know what else to say. They just suck.

Signed up for the 1 ½ hour wave runner tour through this company. Our guides were Matt and Devin, who were extremely knowledgeable and friendly. Rode through calm and rough waves, but all in all a great experience! Will definitely book with them again when we return to the Keys!

Did the all day beach pass at smathers and had a great day in the sun! Started with parasailing then went on to kayak, zayak, and sailed the hobie cat. Very hot day with little to no wind so the sailing was slow but nice for our first time! The staff was very friendly especially the «old timers» and the «juniors.»
We wished we brought more water and snacks as there was only one food truck. But a fun day overall for the price we paid. Definitely a good value.

Jake was the man! Me n my pop had a great time flying through the waves (although my dad couldn’t keep up haha), was an awesome time. would recommend it to anyone!

Well… We signed up for an all-​day beach pass, which included parasailing, at Smathers Beach. We were on the first parasailing group out on 6÷4÷15. While the boat and equipment were top-​notch, the crew left something to be desired. One used the «N-​word» almost immediately once we were on the shuttle boat, and the other made an inappropriate race-​based joke — all in the first 5 mins… The actual parasailing experience was safe and generally fine.
We also spent time doing the other watersports activities — sailing, kayaking, paddle boarding… All of those services, and the folks running those services were great. Matty (Maddie (sp?) was friendly and had great tips and suggestions. The guy that gave us a hobie cat lesson was great as well — and very helpful when we had an unplanned encounter with a sea urchin…
If it weren’t for the racist comments of the parasailing trip, the rating would have been much high (4 or 5 stars), but those sorts of comments are wholly unacceptable.

I would have a given a 0 star if not for the parasailing experience. I feel it was the best and the only stuff worthwhile. For starters they dont tell you pre hand that you have to shell money at each and every step in the do it all adventure. Food was okayish and definitely not recommendable. For people who have come and doing activities first hand they should atleast be told how to do the activity and cons of same. Staff is simply overburdened. Greg the captain was a bit rude as well.

This was my first time going jet skiing. I was a little nervous but ended up having an awesome time! The guides taught us how to ride them and let us free run for a while to get used to the jet ski. The tour itself was pretty cool. Got to chop some big waves going about 40mph. We stopped every 5 – 10 minutes to learn about a different part of key west. One of the highlights was getting to jet ski in the southernmost point of the U.S. All in all had a fantastic time and I will definitely be coming back.

4 of us went on the sunset dinner cruise. what a disappointment!!! other than the initial introduction by the captain, the staff didn’t talk to anyone, didn’t smile and couldn’t be bothered with the guests. The advertisements said unlimited champagne but when my sister tried to order some, then bartender scowled and said they didn’t carry champagne. Then I went back for my second beer and they were out of beer, so I asked for a cup of water. The bartender again scowled and told me she would get it this time but that there was a cooler that I could get it myself after that.

Sadly it sounds as though your experience depends greatly on your crew. We had nothing but good experiences!
All of the crew we encountered seemed friendly, and the crew members we had for our excursions were great. We did the 2 stop snorkel trip first. Kai was super friendly and helpful. It was really choppy when we went out and many, including myself, got sick. He was very kind and attentive to everyone, from us seasick folk to the people having fun in the water. He was great with first timers and made you feel completely capable. We saw lots of fish, a huge barracuda, and dolphins. Despite getting sick, I still had a great time and would go again on a day the water isn’t so rough.
We went on a jetski tour which was amazing and totally worth the price. It was a blast. Highlight of our trip!
We also rented paddle boards and kayaks one day. Made for a great afternoon.
I think the really important thing before going on any of these adventures is to know yourself. The people complaining here seem to be the same type who were at the back of the pack and maybe not so adventurous as others in the group. Know your own adventure level and pick something that is your speed.

Woke up to a windy day and a phone call that our fishing trip was cancelled, so we decided to do the «leisurely» 27 mile jet ski tour around the island. For $ 99, we were able to share a jetski– I was the passenger. I did not appreciate how the cashier asked for a $ 25 tip up-front…which was even more interesting at the end when the guide mentioned $ 10 – 20 being a good tip.
Started out ok, water was not too choppy and I was enjoying it. Then all heck broke loose. I start holding on for dear life as the waters grew even more choppy (5 – 6′ waves). Every bump/​wave we hit I’m literally flying out of my seat. Plus the salt water is hitting me in the face and stinging my eyes, so I’m riding blind, eyes shut.
We stop every so often for a quick tidbit of info with the amazing staff and one jokes that if I fall off, to take the driver with me. I muster a chuckle and we’re off. I am praying to Poseidon to keep me safe but it obviously was not enough. I am ripped off the jet ski, into the blue abyss. I lose my mind, sunglasses, an earring, and start panicking. I’m thinking sharks as the waves toss me to and fro. I’m yelling for help and the driver and guide come to my aide. I’m in the water scared and they seem to not realize that I’m panicked and that this is traumatizing for me– the guide was even laughing! Hello, 1^st time rider here! My fear only worsens here on. I did get to do my own driving and I went pretty slow but at least I had control for once. Bad idea. Water is assaulting my face every second in 5 – 6′ waves and I’m blind riding again. We are going too slow and I switch back to passenger as I simply can’t handle these waves.
I have never been so scared! I am so glad the nightmare ended! I really struggle with why they would take riders out on a day like today when almost all other riders also were talking about how bad conditions were. The guide also indicated that the waves were generally always like this… Save your money and go jet skiing in non-​chop water somewhere like Mexico.

We booked a hobie cat rental and charter boat for sport fishing through an agent here, and although he was pretty helpful at the time of booking, he made a pretty big mistake in that he booked us to be sailing our hobie cat until 1:30 PM and then head over to the sport fishing boat at 2 PM, but the captain of the sport fishing boat (as well as the other two fishers) were told that they would be starting at 1:30 PM. This maybe wouldn’t have been that big of a deal except for that the other two fishers had 6:15 dinner reservations, and the fishing trip is supposed to be four hours, so we had to cut it short because of course my date and I arrived at 2 PM — how in the world could we start the fishing trip at 1:30 PM if you’ve literally scheduled us to be sailing our boat until 1:30 PM and it’s not even at the same location??? And of course starting at 1:30 PM we started getting anxious phone calls from the fishing boat captain, and the other two fishers didn’t look happy with us when we arrived half an hour late, but can you blame them? It’s not a cheap trip and you want your full four hours worth, of course.
Other than that, both the sailing and fishing experiences themselves were awesome (but keep in mind that is because they are provided by third party vendors, NOT sunset watersports which does the booking only). We paid about $ 150 for the sailing and $ 370 for the fishing trip (that includes the gratuity to the captains though, which is 20% and which is fine to pay because it really is a big source of income for them, whereas Sunset takes like 20% or something as a booking fee).