Private Sailing Charters in the Cayman Islands

Enjoy a unique Cayman sailing experience aboard the 47’ Beneteau Oceanis
“Splendour in the Wind”

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Come as you are, it’s an all-inclusive sailing experience with snacks, refreshments, floaties,
and snorkeling gear ready to go.

Swim with stingrays and feed them a treat (we bring snacks for them too!).

Choose one of our Cayman boat charter packages, or create your own personal sailing experience.

“What an amazing time! A group of 13 of us chartered a sail and experienced the trip of a lifetime.”

Trip Advisor Review

A Cayman Island Boat Charter Like No Other

Choose Blue Sky Sailing and get ready for the Cayman sailing experience of a lifetime. Depending on which charter you prefer, you’ll visit Stingray City to swim with the rays, you’ll explore coral reefs teeming with marine life and enjoy a stunning sunset over the beautiful Caribbean Sea. Or you can design your own sailing adventure.

What Makes Blue Sky Sailing Unique?

You’ll sail in the capable hands of professional sailing Captain Orneil, a native Caymanian who can take you places only the locals know about (you can’t even find them on a map!). You’ll be on board Splendour in the Wind, a modern, spacious, fully-equipped sailing yacht all decked out for your comfort with bean bag chairs, staterooms and lounging areas fore and aft.

Go Beyond the Reefs – You can either customize your Cayman yacht charter package, or create a sailing experience that’s entirely yours, and even ask Captain Orneil to take you beyond the reefs to enjoy the thrill of open water sailing in the deep blue Carribean Sea.