Sailing/Catamaran

Cayman Islands Sailing Charters

Cayman Islands Sailing Charters If you’re dreaming of the perfect day on the Caribbean Sea, Cayman Islands Sailing Charters delivers it with ease and island charm.  Step aboard, Be Happy, you have your choice of a 46 foot Leopard Catamaran or a 37-foot Prout sailing catamaran, and let Captain Ben and his friendly crew show you the very best of Grand Cayman from the water.  Known for his easygoing personality, deep local knowledge, and genuine Cayman hospitality, Captain Ben customizes every trip to fit your mood—whether that’s a romantic sunset sail, a private family adventure [...]

Cayman Islands Sailing Charters2025-10-15T19:12:28+00:00

Red Sail Dinner Cruise

Red Sail Dinner Cruise One of the most beautiful Grand Cayman sights is the stunning sunset in the western sky. Red Sail Sports has a huge variety of activities to choose from, but listening to the wind in the crisp sails, the water lapping against the bow, while dining under a thousand stars makes this dinner sunset sail a favorite and memorable activity. They have four 65’ luxury catamarans, the Spirit of Calypso can accommodate up to 70 passengers but for this special evening, they limit the number to just 32 passengers to allow [...]

Red Sail Dinner Cruise2020-01-03T01:31:42+00:00

Stingray Sailing

Stingray Sailing Set sail with Stingray Sailing, one of Grand Cayman’s most loved and highly rated experiences — and a proud Passenger Pick!  Step aboard this beautiful catamaran and let the calm Caribbean breeze guide you toward Stingray City, one of the island’s most magical encounters. Known for its small-group feel and personalized attention, Stingray Sailing is perfect for families, couples, and adventurers of all ages.  What truly sets them apart? Their thoughtful touch — a lily pad designed to help small children (or anyone a bit hesitant) feel safe and comfortable as they meet [...]

Stingray Sailing2025-11-30T20:36:07+00:00

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Passenger Picks suggestions and advertisers are not endorsed by PassengerPicks.com or Val Kegel, but by frequent visitors of the Cayman Islands.

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