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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$375-$1,670
Sailboats
Set sail with these traditional wind-powered boats
$555-$1,640
Kayaks
Who says you need a motor to have fun on the water?
$120-$1,275
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$195-$1,135
Fishing Charters
Let a captain do the driving while you do the fishing
$310-$440
Diving
Explore the ocean depths with trained boat operators
$110-$115
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$185-$235

Sylvia
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
What an amazing experience provided by Israel and Darron. They were both very attentive and made sure that our cups never ran dry. A 3 hour sunset cruise filled with gorgeous views, lots of laughter and beautiful energy. I won't hesitate to reach out to this dynamic duo next time I am in Jamaica!
AA
Abbey
Luxury Private Tours, Rose Island Pigs & Turtles
We had the best time with Ashanti! He took us all around and we got to snorkel and see sea turtles! I would definitely book again!
AW
Andrew
Perfect center console for fishing and beach trips
Top notch service from start to finish. Deidrick, was quick to respond. With 8 hours notice of trip he was able to put together a great fishing trip and catching was the bonus. The staff was amazing Captain Bobby and Sin from the meet and greet the energy from the staff was welcoming if you’d seen us fishing you wouldn’t know we just met 10 minutes prior. Thanks again for great experience. Definitely will be using services again. Captain Bobby , put us on the fish until the fish stopped biting. Thanks Deidrick, Sin and Cpt. Bobby
LS
Lauryn
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
This private rum punch boat cruise provided by Main Squeeze was an absolute 10/10 experience. From the very beginning, Captain Israel was extremely responsive leading up to the trip, answered all our questions promptly, gave clear directions, and offered very reasonable pricing, which made planning completely stress-free. Transportation was perfectly coordinated, and everything ran seamlessly from start to finish. The open bar was flowing with rum punch and plenty of other drinks, setting the vibe immediately. The experience itself was next-level with jet skis, snorkeling, birthday decorations, and the ability to play our own music via Bluetooth, making it feel fully customized to our group. Huge shoutout to the incredible crew—Captain Israel ran the trip flawlessly, Darren, our lifeguard and bartender, kept the drinks coming while making sure everyone stayed safe, and David, our jet ski instructor, made sure everyone felt confident and had an amazing time on the water. The service was truly exceptional. If you’re looking for a private boat cruise that’s fun, lively, well-organized, and absolutely lit, Main Squeeze delivers. Perfect for birthdays, celebrations, or an unforgettable day on the water. Highly recommend!
LQ
Laura
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
We had an absolute blast! Would recommend to anyone! Darren and Israel were so much fun they celebrated our birthday event with us and even decorated the boat for us. They let us play our music and bring food. We snorkeled and they took amazing pictures for us. Book now!
JS
Jodie
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
Best excursion / day of our trip - Israel and Darren couldn’t of done more for us or been more accommodating and fun ! We had an amazing time for our birthday the vibe at sunset was unmatched ❤️ can’t thank the host enough for the amazing memories we got to make
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!

September 13, 2023
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June 02, 2023
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August 31, 2022
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December 30, 2019
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