At Cayman Islands Sailing Charters our crew offer the ultimate personal sailing experience. We want our guests to feel like it is their boat for the day. Come and meet the crew who want to make your private sailing charter an unforgettable experience!


Our 37′ Prout Snowgoose Catamaran

Cayman Islands Sailing Charter Catamaran

“Be Happy” is a classic 80’s catamaran, built  for comfort and speed. With the Cayman trade winds she can reach up to 10 knots under sail. She comes fully equipped for a fun day on the water; on board you will find a stereo, snorkeling gear, fresh water shower, large ice chest, marine toilet, and much more! with lots of space to move around and plenty of places to sit, let us and ” Be Happy” show you a great time on the water!


Captain Benjamin P. Wilson

Cayman Islands Sailing Charter crew, Captain BenBorn in Merritt Island Florida, Captain Ben Wilson is a watersports connoisseur. He has been in the watersports industry for over 10 years and in the Cayman Islands since 2014.

Captain Ben holds a US Coast Guards 50 ton Master Captains License as well as a PADI Open Water Scuba Instructor!

Before Captain Ben arrived in Cayman he has traveled the world; From sailing the BVI’s  to Driving speed boats in Thailand, and Teaching Scuba in Hawaii. Captain Ben Wilson is fully certified, insured and compliant with all regulations. At Cayman Islands Sailing Charters passenger and boat safety is paramount.

Additional Crew

Rose Massingham

Cayman Islands Sailing Charter Crew, First Mate Rose

This Cayman Islands Sailing crew member is a wildlife expert, and handy first mate. Rose was born in England but prefers the sunny Caribbean. 

Rose has a Degree in Zoology, a RYA 2 powerboat driving licence as well as being a qualifed PADI Divemaster. 

A true water baby it is no wonder Rose ended up in the Cayman Islands, she has been here for three years so far, first coming to island as an underwater photographer. With Rose on board you will be sure to have an informative and interesting charter!