We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$590-$1,800
Kayaks
Who says you need a motor to have fun on the water?
$150-$1,435
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
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$100
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!
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.
Darren
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
Israel and Darren were amazing hosts for our day on the water around MoBay. Highly recommend! Great communication with booking, on time pickup, and great rum punch and stops along the way… Book them for a great day on the water!
JR
Jenna
31ft SeaRay Sundancer Luxury Boat Chartering in Grand Cayman
The crew was amazing! This experience was so magical. We got to swim with sting rays, see star fish, visit rum point, and drive the jet ski around at sunset. We had two young kids on the trip, and both members of the crew were incredibly accommodating, helpful and patient. Most people on the trip said this excursion was the overall highlight of our Grand Cayman trip. 10/10 recommend!
DS
Dakota
Glacier Bay Private Boat Charter Tour in Turks and Caicos
I would highly recommend this experience—10/10! My friends and I had an amazing time celebrating my 30th birthday. Cheno was an excellent captain, making the trip even more memorable with his island knowledge and delicious rum punches. We got to visit several incredible spots, and I even had the chance to swim with dolphins!
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!