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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$300-$1,495
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$130-$1,665
Sailboats
Set sail with these traditional wind-powered boats
$475-$1,720
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$155-$495
Kayaks
Who says you need a motor to have fun on the water?
$95-$455
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$245-$1,310
Diving
Explore the ocean depths with trained boat operators
$60
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$675
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$310
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

Inyene
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
Isreal was amazing! The boat was perfect for my friends and I. He even decorated for my birthday which was such a sweet touch. He provided snacks and beverages. Our favorite part was snorkeling and learning about the wildlife. It was the highlight of our trip and I would recommend!

Amani
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
I want to think Israel and his partner for hosting me and my sister for my 24th birthday on this beautiful yacht. It was set up so nicely & it was such a dream. I just want to also thank Israel for his patience, humanity and his professionalism while it rained on the actual time I was supposed to go out on the waters. Israel waited for the rain to stop to accommodate me and my sister. He was not money hungry and neither was he being impatient and trying to rush me and my sister. While me and my sister went to go grab a bite while it was pouring. Israel made sure to come up to the restaurant and check on us girls. When the rain stopped we immediately went on the boat , got a chance to play in the water and let’s say Israel was an awesome DJ!! lol I got amazing pictures. This was my first time in Jamaica February 2025 and I felt very welcomed . I said this plenty of times, but again thank you so much Israel for making my birthday the best birthday.
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william
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
Top notch from pick up/drop off, to the 3 hour tour. They nailed it! Beautiful water, they took our pictures without us having to ask & showed us the beautiful coastline. Great swim & beach stop was perfect! Seeing the flights coming in for landing was a great surprise! They even provided us with a light lunch and were eager to serve! Anticipating our needs every step of the way. I even got great treatment after scraping my leg while swimming. GENUINE TEAM! Music, food, service we can't say enough good things about them. Don't hesitate just BOOK THEM xoxo Ike & Pennie from WV/Chicago
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!