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    Gilligan's Watersports

    3.9 (83 reviews)
    Open 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

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    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.

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    Beach Weekend

    Beach Weekend

    4.0(27 reviews)
    7.0 mi

    We rented for a special occasion ! This was our 4th time renting from beach weekend ! It was our…read morefriends sons graduation trip and this was supposed to be best day of the 6 day stay with us on emerald coast . I speak highly of beach weekend because the kids working the docks are always so nice and accommodating . But this time we waited 20 mins with our dolley cart loaded while everyone working inflated floats for customers and walked around ...... we were just about to say something then someone walked up to give my hubs the boat walk through . This time we didn't get a boat with the complimentary huge cooler . It was a smaller boat . Too late to switch but ask for that one if you can because it's nice transferring everything to there big cooler and not have 5/7 yetis on one pontoon . This trip the boat we rented broke down 1/2 way to crab ..... it delayed us over an hour waiting for new boat . We swam around where we were parked and chilled. Totally fine and happy waiting in gorgeous clear water off oakaloosa . When they came to replace it we had to unload current boats bags and coolers for 10 people to new boat . Not bad but kinda added more time to find where everyone's stuff was after we quickly moved . We were kinda annoyed he said we could have an extra 30 mins added to our trip . We told him we were delayed over an hour so he said 1 hour passed our time scheduled to return ...... It's likely we will rent from them again in July because of all the great experiences we've had in the passed . They do military discounts and it's pretty reasonably priced . Plus they drive the boat out and in the marina for you...... I would have been happy if they gave us more then an additional hour that we missed or a discount on the next rental ..... we got there at 10:30am . 30 mins before our check in time . But we legit didn't get to crab till after 1 between waiting to load then the boat beeping and stalling out 1/2 way there .

    Great experience with this company! We hired a charter & captain to take a group of us from the…read moremarina to Crab Island - about a 30 minute boat ride. Our captain was super friendly and most importantly made sure our ride was safe. He went over the top while we were at Crab Island - blowing up rafts, going to the food boats for us, etc. We booked a four hour charter but could have stayed all day, we had so much fun!

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    Beach Weekend
    Beach Weekend
    Beach Weekend

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    Buccaneer Pirate Cruise

    Buccaneer Pirate Cruise

    4.5(138 reviews)
    0.8 mi

    We did this cruise in June 2026. Our two 5 year old grandsons had a ball. The pirate actors were…read moreincredible and believable. The kids participated in sword fights, water gun fights, a treasure hunt and more. This is a must do with kids. It is action packed the whole time and well worth the money!

    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.

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    Buccaneer Pirate Cruise
    Buccaneer Pirate Cruise
    Buccaneer Pirate Cruise

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    Gilligan's Watersports - boating - Updated September 2026

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