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    Gilligan's Watersports

    3.9 (82 reviews)
    Closed 8:00 am - 8:00 pm

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    Anchored at Crab Island

    Yesterday, we had a PERFECT pontoon day, set up by Jared and Brendan and Captained by my husband. Jared was efficient and super-friendly with the paperwork and helping us load our cooler into the boat. It was a bit windy so he suggested a sheltered spot we could motor to, so we could chill a bit before anchoring at Crab Island for the afternoon. Brandon gave Captain husband a quick how-to on boat operation and pulled us out of the slip then handed over to us. The boat was a brand new Bentley. It was clean, and everything worked perfectly. There are a lot of outfits to choose from and prices vary a lot. Gilligan's did not 'nickle-dime' us or try to upcharge. We got great value and recommend them most highly!

    New Yamaha Waverunners
    Aaron S.

    My son and I did the dolphin tour on the Waverunners and it was one of the best times I've ever had in Destin. 120.00 a piece to go in search of dolphins was a great value in my opinion. The guide was a nice college age kid and we got a period of time where we could enjoy the performance of the Waverunners. Will absolutely visit Gilligans next time in Destin.

    Renee S.

    I highly suggest the jet ski dolphin tour. Yes you can just rent the jet skis and try to find dolphins yourself but the guided tour will show you all the secrets spots and take you to places off Santa Rosa that you can see the bottom of the ocean. Someone jet ski flipped over,our guide jumped off his turned it back over helped two guys back on And rescued his slides. I wouldn't suggest if you get motion sick due to tour being 2 hours long.

    Parasailing
    Crystal H.

    Great parasailing experience with Captain Travis and Jarod! So much fun and very peaceful! We even got to see home dolphins on the way back. Definitely recommend!

    shit shack

    What a joke of a company. Brought my family 45 minutes out to this run down piece of shit shack to be told that our booking was cancelled due to a little wind. We were here 30 minutes prior to our reservation as required just to be turned away when we approached the fucking shack. The lazy ass bitch behind the counter told us that we would just get a refund rather than try and reschedule us like wtf? Would not recommend this place, there's definitely nicer places than this fucking joke of a place.

    Ciara B.

    I went parasailing for my birthday on 07/30/2019 We had a free voucher with my Gibson Beach Rental for free parasailing for one person we purchased an additional flyer and photo memory card. I believe our crew was Troy and Travis. They were really cool and the made the whole process smooth and stress free. I was very nervous but I felt very safe pretty much the entire time. We were able to bring along my bag with towels and water. They give you the option to get dipped in the water or stay dry, we chose to get dipped and let me tell y'all... heart ATTACK central. We were dipped in some jellies but thankfully were weren't stung. Also they got great pictures on the card! Don't forget to smile guys. The whole ocean is so beautiful from up there it's like a swing in the sky, we saw lots of different kind of marine life.

    Parasailing

    Parasailing...At first the price made me nervous but it was worth every penny. Are Caption and his helper Connor were awesome. The earlier you go the better because it was pretty hot. Definitely recommend sun screen and lots of it. You have the option of being dipped in the water, i would definitely do it! Came in kinda fast but it was fun. experience was about an hour and a half. Left 10 mins after we were supposed to but understandable.

    The pictures we had to pay extra for were all very blurry and most were not zoomed in.

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    2 years ago

    Great experience parasailing with Lee and Dillion! My family had a great time and made wonderful memories!

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    6 years ago

    Went on the dolphin tour ride and our tour guide was incredible she was super patient with us.

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    4 years ago

    Had amazing time on jet ski and parasailing one right after another, highly recommend checking them out if you are in town for a weekend!

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    Page 1 of 3

    Ask the Community - Gilligan's Watersports

    Review Highlights - Gilligan's Watersports

    Nate was an excellent tour guide and did his best to find them, taking us to the gulf and the bay.

    Mentioned in 6 reviews

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    Buccaneer Pirate Cruise

    Buccaneer Pirate Cruise

    4.6(134 reviews)
    0.8 mi

    An interactive, fun experience for families that have young children. I even noticed preteens…read morehaving a blast. Unfortunately, for myself and my family we were sold on this idea of a pretty cool pirate ship that tours the island of Destin. Not at all with this ship does. This cruise is solely intended to entertain children while you explore a small area of the waters for example passing crab Island starting just a short distance away from Harbor Walk. We were lucky enough to see a dolphin take a quick flip above water, but if you blinked and missed it, which some people in my group did, then you missed it but it's not advertised as part of the experience so for those of us that saw it, we were lucky. I do find that there are many dolphins and you get to see them probably any day you're on the water. The ship is exceptionally clean, and I loved the laboratory facilities. Not your typical tiny bathrooms that you find on a boat. We did order the fast on boarding Tickets, which I did not feel were necessary. No one asked us for it and when we got to the ship, we were instructed to walk to the front just like everybody else and had to wait for one family to board ahead of us as they only board one group at a time. In my mind that family did not have a fast on boarding, however, who knows. We were not asked for the Pass and there was no line or sign to indicate what side to stand on if you had a fast on boarding. Maybe this is more valuable during peak season but definitely not now.

    We had a great time on the cruise! Brought the family to Destin and my girls wanted my grandson to…read moreexperience a Pirate Cruise like they did when they were little. It was outstanding. The staff were all helpful and entertaining to all onboard that I saw. Interacting with as many guest as possible. Cracking jokes, dancing with the kids, training them to be a "Pirate". I would highly suggest this place for more than just the cruise. They are outstanding believers in Jesus Christ and also support missions. I am sure your family would enjoy everything about it.

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    Buccaneer Pirate Cruise
    Buccaneer Pirate Cruise
    Buccaneer Pirate Cruise

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    Crab Island Dolphin Tours - My husband finally relaxed!

    Crab Island Dolphin Tours

    4.7(22 reviews)
    0.4 mi

    8 of us went on this tour from 10a-2p. It was definitely the right time to take it. The parking lot…read morewas empty and by the time we got back there wasn't a spot to be seen. During our tour Tonya was our captain. She was amazing and very knowledgeable. We spent an hour watching dolphins and then the next 3 on a sand bar. The sand bar was awesome for the adults and kids. She put out a floating mat to lay on and parked right next to an inflatable obstacle course for the kids to play on. While on the sand bar she took a ton of photos and videos of everyone so you didn't have to worry about it. At the end of the tour she sent them to us at no extra charge. If we ever go back to Destin FL then we will for sure rent the boat again!!!! Hopefully Tonya is our captain again! NOTHING NEGATIVE ABOUT OUR EXPERIENCE!!

    Beautiful, relaxing, and fun. We did the 6 PM sunset cruise. Captain Brian did a fabulous job of…read moretaking us directly to the dolphins.. We were able to see so many! We saw a sea turtle, stingray, and herons too. We also stopped at a Sandy pristine beach and took a walk. It was so relaxing and beautiful. We also time to crab Island perfectly for Sunset Captain Brian took tons of pictures of us in a very thoughtful way with the sun sinking low in the background. the pictures turned out beautiful. What a great trip. I would highly recommend if you want to truly relax rent a private boat with a captain like Brian.

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    Crab Island Dolphin Tours - A perfect sunset!

    A perfect sunset!

    Crab Island Dolphin Tours - My love!

    My love!

    Crab Island Dolphin Tours - Our 30th anniversary trip!

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    Our 30th anniversary trip!

    Gilligan's Watersports - boating - Updated May 2026

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