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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$335-$1,520
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 Charters
Let a captain do the driving while you do the fishing
$150-$500
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150-$500
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
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$310
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$665
RM
Renee
46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included
I had an absolutely amazing time! I was well taken care of and pampered! Everything was wonderful from start to finish - great communication, amazing and attentive staff, delicious food, excellent service, beautiful decorations and a yummy surprise birthday cake! What a memorable birthday! Thank you all again!
SL
Skylyn
Private Pink Luxury Yacht in Montego Bay
My family and friends rented this yacht (8 people) it is our first time in Jamaica and we had a wonderful time. They were so accommodating great food and drinks and we had a blast. Highly recommend!!!
KH
Kayla
Luxury Cabin Cruiser Yacht for Charter
Captain J and Sam were incredibly accommodating from start to finish! We had 2 girls who get seasick easily and they made adjustments to ensure they were comfortable. They also made my birthday feel super special with drinks and cupcakes! I’d book again and again.

Mark
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
We had a great time on our boat cruise. From booking to docking, Israel and his first mate were professional, The cruise was educational and fun. Thank you for showing us a marvelous time.
DP
Dean
Enjoy cruising Montego Bay Coastline on a 30' SeaRay Yacht w/unlimited Rum Punch
5/5 all around, had a great time for a sunset cruise.
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!
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!

August 01, 2023
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November 23, 2022
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October 03, 2022
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April 14, 2022
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December 11, 2020
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December 29, 2019
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Boat Rentals
Jamaica
St. James Parish