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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$300-$1,345
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$90-$1,535
Sailboats
Set sail with these traditional wind-powered boats
$285-$1,600
Fishing Charters
Let a captain do the driving while you do the fishing
$125-$550
Kayaks
Who says you need a motor to have fun on the water?
$75-$540
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$150-$1,365
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
JD
Jepera
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
This was an amazing experience. Mr. Israel was awesome and made us feel very comfortable. His hospitality was great. I will definitely be back. The boat was perfect for my birthday.
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!
Michelle
31ft Chaparral Yacht Charter from Cayman
We had an incredible time visiting Stingray City and snorkeling! From start to finish, the experience was seamless, professional, and full of unforgettable moments. The crew was friendly, knowledgeable, and clearly passionate about what they do. They made us feel safe and welcome right away, and their enthusiasm was contagious. They provided great instructions and fun facts about the stingrays, which made interacting with these amazing creatures even more special. Stingray City was everything we hoped for – surreal, thrilling, and beautiful. Getting to stand in crystal-clear water surrounded by gentle stingrays was a once-in-a-lifetime moment. Afterward, the snorkeling stop was just as amazing. The water was so clear, and we saw tons of colorful fish and coral. The guides even pointed out hidden sea life we would have missed on our own. The boat was clean, spacious, and well-equipped with everything we needed. It felt like a private, VIP experience. Whether you’re a first-timer or a seasoned snorkeler, this tour is a must-do in Grand Cayman. Highly recommend – they delivered an experience we’ll never forget!
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.
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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December 30, 2019
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