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    Paradise Pontoon and Captain Services

    2.9 (55 reviews)
    Closed 6:00 am - 7:00 pm

    Services - Paradise Pontoon and Captain Services

    Boat charters

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    Michelle S.

    Captain Shay was our captain. The group organizer received a last-minute price increase. We were over-quoted, and he didn't have a license for more than 6 people, but said he could take care of a group of 18 with two boats. There was never a second boat so he called Crab Island Jimmy's Charters. After the last group boarded an hour and 15 minutes after the original launch time, we were only 20 minutes into the trip when we were pulled over by the Sheriff and Coast Guard. Captain Shay was arrested for being under the influence. Upon further review, he has YEARS of criminal history and fines. Do your research on this company. Book with Crab Island Jimmy's Charters instead. They saved the day and made our experience!

    Kiarra G.

    What is funny is we actually came to Dustin based off of a Facebook video that we seen. Little did I know the video that I seen was the one that Captain Shay created such a small world. We were visiting Destin for my 30th birthday all the way from California and he made our experience amazing. He goes above and beyond to make the experience personable, relaxed, and is very accommodating... he even took us to the convenience store. Captain Shay has everything you need on the boat including sun tan lotion, floaters, towels, cold drinks, and even a droid! Very nice touch at the end to be able to take a video home of the fun you had at crab island! I would deathly recommend and he made the transaction seamless, no credit card needed to reserve however he treats his gas more like family. Don't think twice and book your excursions with Captain Shay! P.s. Captain Shay I still want my VIP gold card!!!

    At crab island with Cpt Shay!
    John G.

    Family of 5 from Texas - Captain Shay and his pontoon were exceptional! Arrival and boarding was a little unconventional but did not take away from our experience at all. Cpt. Shay is a bright and energetic personality that was a pleasure to be around. He kept us all entertained with local history and lore while expertly handling his craft through busy harbor waters. One thing we did not expect was that Cpt. Shay had a drone with him that he used to take aerial video of our kids at play on the Crab Island obstacle course. I expected to be made an offer to 'purchase' the video footage as an extra, but nope... this was just something our fine Captain did as a part of his service for free! mIt was great to be able to take some video home of our vacation. Totally unexpected and very much appreciated. We will definitely be back to Destin next year and already have plans to meet up with Captain Shay again. Highly recommended.

    On our way to a treasure hunt.

    Finally, a captained pontoon rental business that cares more about the people than the money. They provide everything except the food you want to eat and the drinks you want to drink. The boats are all in top shape, clean, and completely equipped for however many hours you spend on the water. They let YOU decide where the boat goes and how long it stays there. They become your personal bar tenders, servers, and tour guides once you get on the boat. We saw dolphins, sea turtles and other marine life on our dolphin tour. Went into the harbor and did a slow tour of the big boats and waterfront homes. Finally ended up at famous Crab Island and enjoyed the knee deep water there. They had several water toys and floats we used while we were there. Pick up and drop off location was very convenient with lots of free parking and only 20 feet to the boat. We WILL be back to enjoy more fun with this company. The new owners/management is doing things the way they should be done. Now they even have no hassle booking online.

    All the reviews I read was wrong my family enjoyed themselves to the fullest recommendation to anyone
    Cora O.

    Enjoyed our day will recommend to anyone he was awesome tended to all of our expectations and we seen so many dolphins

    Texts to Captain Shay
    Olivia G.

    I booked my trip in December 2018 for an April 2019 bachelorette party. After numerous phone calls and texts Captain Shay never answered and neither did his "answering service". Do not book Captain Shay. It is a nightmare.

    Texting confirmation and never showed. Never texted back or answered phone.

    Shay ditched us. We booked a trip MONTHS ago for a bachelorette boat ride to crab island. He communicated multiple times before trip with confirmation. We get to harbor to be picked up and he doesn't show and won't answer the phone. Thankfully we hitched a ride with Max from another company and made it out for half the time with same price. Very disappointed by this company. Do not recommend booking with Shay.

    Aye aye Captain!
    Jeff P.

    Super personable when I called on the phone and no need for a credit card for a reservation. We rented 1/2 day (5 hours at this place apposed to 4 elsewhere) and they were there ready to go when we pulled up15 minutes early. They are literally a few hundred yards from crab island, had maps, auxiliary cord for music, etc....even helped carry all our stuff which really helps when you have young kids. Boat was nice, ran great and had no issues. Great trip!

    Captain Shay, my husband, and my 2 sons! They enjoyed being a the captain and the end of our trip! Such an amazing experience!
    Kanita W.

    Captain Shay was amazing!! There is no way we would have been able to have an amazing time without him. He took photos using his drone, took us sight seeing, and even let my boys drive the boat. We had an awesome time and look forward to it again next year! The boat was brand new and clean. Spending hours on crab island was amazing.

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    Page 1 of 2

    Ask the Community - Paradise Pontoon and Captain Services

    Review Highlights - Paradise Pontoon and Captain Services

    Shay and Terry were great from the first phone call to helping us load up our gear when we left!

    Mentioned in 3 reviews

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    Crab Island Dolphin Tours - My husband finally relaxed!

    Crab Island Dolphin Tours

    (22 reviews)

    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.

    Cruise Destin Bay - Beautiful Florida sunset.  Let us make your stay memorable.  Join us on a Sunset cruise available each evening.

    Cruise Destin Bay

    (1 review)

    We had a wonderful dolphin excursion with Captain Harry! We actually ended up having the boat all…read moreto ourselves, which made the experience even more special and relaxing. The weather was perfect -- a little gloomy, but still absolutely beautiful out on the water. Captain Harry was witty, knowledgeable, and made the entire trip so enjoyable. We learned a lot, had a fantastic time, and truly appreciated the personal experience. We'll definitely book again and highly recommend this excursion to anyone looking for a memorable time on the water!

    From the owner: Experience the best Destin boat tours with Cruise Destin Bay, offering unforgettable Crab Island…read moretrips, sunset cruises, harbor sightseeing, and dolphin-watching tours on the beautiful Emerald Coast. Our licensed and experienced charter captain takes guests through Destin Harbor, into Choctawhatchee Bay, and out to the famous submerged sandbar at Crab Island, one of Florida’s most popular boating destinations. Whether you’re looking for a relaxing day on the water, family-friendly fun, or a romantic sunset cruise, our tours are designed to showcase the natural beauty of Destin, Florida. Enjoy swimming in clear emerald waters, watching marine wildlife, floating, or simply cruising the bay while taking in the views. We provide comfortable seating, coolers with ice, cups and water, Bluetooth music so you can play your favorite playlist, and floating chairs, a lily pad and paddle boards for extra fun at Crab Island. Nearby food and drink boats offer snacks, ice cream, and local favorites to complete your day on the water. Our goal is simple: safe, memorable, and fun Destin boat adventures for couples, families, and groups looking to experience the best of the Emerald Coast. Book your Crab Island boat tour, Destin sunset cruise, or our Destin boat ride today and see why visitors choose Cruise Destin Bay for unforgettable days on the water. A Destin Top-Rated charter boat company with hundreds of 5-star reviews.

    Paradise Pontoon and Captain Services - boatcharters - Updated May 2026

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