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A Grand Cayman Private Charter With Five Star Charters Is The Perfect Way To Set Your Spirit Free

Five Star Charters’ Grand Cayman luxury private charter is ideal for couples, families and friends seeking a magical, first-class experience on the glorious crystal clear blue waters in The Cayman Islands. Our team will greet you as you board our luxurious 48’ Sea Ray Sundancer cruiser.

This pristine yacht provides all of the comforts of home including an air-conditioned cabin for when you want a break from the sun. All you need is a bathing suit - we’ve got the rest covered: beach towels, sunscreen, sun gear, snorkeling gear, jet ski, light snacks, and cold drinks.

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Your Five Star Experience

We offer half-day (4 hours) and full-day (7 hours) charters for you to customize with the perfect blend of activity and relaxation. A Welcome Aboard Five Star Charter Signature Cocktail, rum punch (non-alcoholic versions available upon request), bottled water, soft drinks and delicious hors d'oeuvres are included with every cruise. Learn More >


Be the first to greet the stingrays at Stingray City Sandbar with this early morning cruise.
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A half-day cruise customized with just the right levels of activity and relaxation.
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Let go

A full-day cruise tailored to be your perfect Five Star day on the water.
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The Five Star Experience

I can’t recommend Five Star Charters enough. From the moment we stepped on board, our every need was anticipated and taken care of. It really was a Five Star luxury experience. I left feeling so relaxed and the children couldn’t stop smiling. Read more >


Our group included two seniors, three sons in their 40's and their wives, partners and grandchildren...Everyone agreed, this was one of the most wonderful things we have ever done as a family. Thank you "Five Star." If we could give you ten stars - we would. Read more >

Mark C.

We are beyond blown away with the luxury, the quality of the trip and the staff! We felt like ROCKSTARS! P.S. How do you add stars to your 5 star charter? We LOVE you guys. Read more >


Five Star charters is AMAZING! The boat is beautiful and luxurious, we felt spoiled (in the best way) the whole time by the amazing crew...I will forever recommend this company and crew to anyone visiting cayman. A can’t miss. Read more >

Jane S.

We charter often and the crew was totally professional, knowledgeable, and super nice. We will hire this crew and boat again without hesitation...Great boat and crew! Read more >


Five Star should change their name to 100 star charters!! From the minute you start to plan the charter until the last person gets off the boat, the whole team are on point! Fabulous food, fabulous drinks, so many activities set up for us all to use (our floating bar was a highlight!). So many personal touches and little surprises! Read more >


The crew were absolutely amazing and very doting on our every need. Not a thing was missing and we were able to snorkel and dive in some of the best places. Having been to Grand Cay a few times already I was surprised at their knowledge of the "off the beaten path" places that were so nice. They even did up the boat with a Happy birthday banner and got me cake as well! Can't wait to visit again. 🙂 Read more >

Lance S.

Five Star Charters is luxury at its finest. If you want a high-end, personalized experience, Five Star is the way to go. There is no comparison to other charter companies in Cayman...trust me, we’ve been on almost all of them. Before my family and I even stepped foot on the boat, we had great expectations, however, when we got there, we were absolutely blown away. Five Star Charters is truly the best of the best. Read more >


By far, this was the highlight of our trip. Our only regret was not booking a full day trip with them!! Next time, we will definitely not make that mistake. Look no more, seriously. Book with Five Star Charters!!! Read more >

Natalie A.

WOW! Highlight of our vacation in Grand Cayman! The perfect combination of professionalism and friendliness! We were eleven women of ages spanning from 36 to 64 with a wide range of abilities and levels of adventurousness. The fabulous crew handled every single one of us beautifully! Thank y’all for a lovely, lovely afternoon! Read more >