Come Sail With Us

Cayman Islands Sailing Charters offers a private charter experience like no other in Grand Cayman. On our catamaran you will visit your choice of top destinations in ‘island time’ style. We pride ourselves on offering a personable trip, tailored to your needs. So you can savour the relaxing experience of sailing in the clear blue Cayman waters.

We have flexible packages to suit everyone.  Here are some examples of groups we have welcomed on-board previously:

  • Families, friends and travel companions.
  • Wedding parties
  • Sailing enthusiasts interested in blue water sailing.
  • Private groups of cruise ship passengers.
  • Corporate team-building groups.

Our Packages

Click on a package below to find out more about it
Snorkeler on the surface from below

Bio-Bay Tour Package

Investigate one of Grand Cayman’s natural wonders with our Bio-Bay Tour Package! An incredible, private experience for all ages which ...
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Catamaran Be Happy in Grand Cayman

Full-Day Sail Package

Our full-day sail package is our most popular option, guests can maximise their time exploring the best Grand Cayman offers ...
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Captain Ben is helping a little girl steer the Catamaran

Half-Day Sail Package

Our Half-Day Sail Package is perfect for smaller groups, first-time visitors and families, who want to experience Grand Caymans finest ...
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Guests on a sunset sail with Cayman islands sailing charters

Sunset Sail Packages

Our Sunset Sail Packages are the best way to end a day in paradise: on the water enjoying a beautiful ...
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Holding a Stingray at Stingray City with Cayman Islands Sailing Charters    

Mission Statement 

At Cayman Islands Sailing Charters we offer personable, private sailing charters tailored to your specific needs at competitive prices.

Visit Grand Cayman’s most famous attractions and its more hidden ones. As our guest you can enjoy sailing, snorkeling, paddle-boarding and scuba diving on our 37′ Prout Catamaran “Be Happy”, skippered by a U.S. Coast Guard Captain.

Join in and learn how to sail, or sit back, relax and unwind on your private sailing trip in and around Grand Cayman. Savor the peaceful sound of the wind on the sails, the blue water lapping against the sides of the boat and take in the gorgeous views. With Cayman Islands Sailing Charters you will have the very best day!

Our boat is your boat, come Sailing in Grand Cayman with Captain Ben!

Find out more about the different packages we offer
Contact Us to find out more