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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$65-$450
Kayaks
Who says you need a motor to have fun on the water?
$75-$790
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$170-$790
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$65-$100
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$115
Fishing Charters
Let a captain do the driving while you do the fishing
$115
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Erica
Most Badass Party Pontoon in Pensacola ! FREE Amenities !
Cameron was the BEST captain! So friendly and fun, he made sure we had a blast! It was truly the highlight of our girls trip. He did whatever we wanted to do and was a fantastic DJ as well! I highly recommend him whether it’s for a family boating trip or for a party vibe, he will get the job done! We love Cameron!!!
DR
Dawn
Brand New 2024 Double Decker Tritoon! Crab Island/Destin
This boat was amazing! Had the best time with our friends and family after our wedding!
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Sami
20' Bennington pontoon, Yamaha 70HP, up to 9 people - gas included! Bay Pines
Nice host and very communicative. Good value and scenic area.
KB
Kristina
24ft Superior Toons Double Decker Pontoon in Destin, FL
I highly recommend booking with Gentry on Island Therapy. The pontoon was incredibly well taken care of and perfect for an outing to crab island. We wanted to see dolphins as well so Gentry took the time to find some and let my kids watch before heading to crab island. He is so knowledgeable about crab island and the best places to set up. Whenever we wanted something from a vendor he would radio someone and they would be right there to help us. Further, he set up a big Lilly pad mat and innertube for us to float on that was attached to ropes from the boat. The entire boat was well thought out in order to have the most fun and relaxation possible on vacation. We loved the hammocks on the boat too! We would definitely book with Gentry again!
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Sue
24ft Superior Toons Double Decker Pontoon in Destin, FL
Great experience. Our first time to crab island. Captain Gentry even was patient with an unfortunate event of my husband losing his wedding ring! Gentry quickly provided us masks to help find it. Let us play our music. Was a very good experience. Ps…we found the ring!!
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Nicole
45' Hatteras Private Luxury Cruising Yacht in Destin, FL
Matt was an incredible host who provided our group with a memorable charter experience for my sister's bachelorette. Captain Ron and Crewmember Lisa went above and beyond for us. The trip started out with us docked due to the rain, but they did everything they could to make us comfortable. Once the rain cleared and we were out on the water, they made sure to provide us with every opportunity we wanted from docking out on Crab Island to seeing dolphins. I would recommend anyone looking for some fun on the water in Destin to reach out to Matt and his team.
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!