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Cayman Islands Sailing Charters offers you a personable, private sailing charter, tailored to your specific needs at competitive prices. Visit Grand Cayman’s most famous attractions, and its more hidden ones, and you can enjoy sailing, snorkelling, paddleboarding and fishing on their 37’ Prout Catamaran ‘Be Happy’, skippered by a U.S. Coast Guard Captain.

What to Expect

Our family did the half day cruise. Captain Ben was delightful! He took us snorkelling and we saw beautiful sea life, he gave us a great tour of the Sting Ray Sandbar and we just had a beautiful day sailing! We had so much fun we went back for the evening bio-bay sail, the next evening for a gorgeous sunset, which was incredible!

The M

Capt Ben was great - took us out for a 1/2 day - starfish point, sting ray city, snorkelling. A beautiful world underwater! Nice cruise under-sail to end the day. Gave us good recommendation for other island activities.

George C

This was an unbelievable experience and beyond our expectations! Captain Ben had excellent communication from the time we booked our excursion to the start of it! Very accommodating with our family of 8. Captain Ben was so knowledgeable, friendly and interactive with our family getting everyone involved, we loved spending the afternoon with them! Stingray City Sandbar was breathtaking! Learning all about these amazing creatures you just simply fell in love with them. Starfish Point was where we learned and held these slow crawlers starfish which are amazing. We definitely will be returning customers next time we're back in Grand Cayman! Thank you for making one of the best days of our lives!!

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  • Personalised private daily boat charters for up to 20 guests from 2 to 8 hours
  • Choose from a full day, half day, sunset sail, sunset dinner cruise or Bio Bay tour
  • Experience Stingray City and snorkel the Coral Gardens and the Barrier Reef. Visit Starfish Point and the mangrove forests around Booby Cay. Try fishing too!
  • Discover Bioluminescence Bay at night
  • Trips include fresh fruit, light snacks and bottled water


Full Day Sailing Charter

With a full day’s sail, which is up to 8 hours for a maximum of 20 people, guests can maximise their time exploring the best that Grand Cayman has to offer.

Recommended for all ages

Up to 8 hours
From US$1250

Half Day Sailing Charter

For groups of up to 20 people enjoy a half day/ four-hour sailing package where you can visit two or three locations including Stingray City Sandbar, Starfish Point, a snorkel spot, Rum Point, Booby Key Mangroves and more!

Recommended for all ages

Up to 4 hours
From US$750

Sunset Sail

Catch the best sunset view out on the open sea.

Recommended for all ages

2 hours
From US$400

Bio Bay Tour

Experience the gorgeousness of swimming in bioluminescence in Cayman’s famous Bio Bay.

Recommended for all ages

3 hours
From US$500

Sunset Dinner Cruise

Enjoy a beautiful Cayman sunset and a delicious dinner.

Recommended for all ages

2 hours
From US$500


George Town Yacht Club
George Town, Grand Cayman

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