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Kayaks
Who says you need a motor to have fun on the water?
$150-$1,435
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$585-$1,800
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$180-$1,085
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$180-$600
Sailboats
Set sail with these traditional wind-powered boats
$900-$1,800
Diving
Explore the ocean depths with trained boat operators
$115-$600
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$275-$450
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Amanda
31 Foot SeaRay from Cayman
We had the most amazing day with this crew! My kids said it was the best day we had on vacation. They got to swim with stingrays, play sand volleyball at rum point and snorkel! Amazing experience!
Angie
Hatteras 55’ Sportfish Motor Yacht in Ocho Rios!
This was such a fun experience for our group! Vaughn and his crew are friendly and welcoming. From taking us to the private beach to helping g with all of our requests it was great!
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.
AK
Ashley
31 Foot SeaRay from Cayman
We had such a great day and really enjoyed the relaxed experience. Yarick took us to some great snorkeling spots, stingray city, and even made us some ceviche. It was really easy to relax and just let the day unfold. Thanks again for making it a really memorable afternoon!
MM
Maurine
31 Foot SeaRay from Cayman
Nick was an amazing captain! We had so much fun today fishing and exploring Stingray City. He was great with our 4 year old. Highly recommend to families coming to visit Grand Cayman.
Ericka
Hatteras 55’ Sportfish Motor Yacht in Ocho Rios!
5 out of 5! The vessel is beautiful and well maintained. The crew was nothing short of amazing. Everyone was attentive and helpful. We had an unforgettable experience. Thank you Vaughn! We will certainly book again when we return to Jamaica.
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!