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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$215-$460
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$260-$370
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$210-$390
Sailboats
Set sail with these traditional wind-powered boats
$380-$490
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$375
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Christopher
Charters with Captain Bibi on a 30ft powerboat in Grand Cayman
A group of 8 of us had an amazing time with Captain Bibi on our recent visit to Grand Cayman. The boat and crew were wonderful. Captain Bibi was very knowledgeable about stingrays and have us the opportunity to interact with one. They also took great pictures of the entire experience and the family will remember it forever. Unlike other other operators, we never felt rushed at any of the spots by any set itinerary or hard end time. We look forward to using Bibi again in the future and will never look elsewhere.
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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!
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Haven
Enjoy Cancun in 32ft Wellcraft for 6 people!
Captain Alfredo and first mate Oscar were very friendly and helpful. The boat had an ice chest full of beverages and the guacamole was delicious. Cancun has some of the prettiest water on the coast planet. Taking a ride with Alfredo and Oscar is a great way to see it.
RL
Russell
32' Boston Whaler Conquest with large cabin & AC, in lower Florida Keys
This was a great boat. Navigation was top of the line. Everything worked great for our family.
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Melissa
31ft Chaparral Yacht Charter from Cayman
We absolutely loved our trip. The captain was fantastic. Very knowledgeable and kind. He got in the water with us and taught us everything we needed to know. He even got my daughter to touch the starfish when we couldn’t get her too!! Thank you for such a great experience! You made it absolutely wonderful for our family. If we ever come back we would definitely book again.

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!
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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August 31, 2022
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December 30, 2019
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