About Captain Rick

Captain Rick Hubbard has been sailing since he was nine years old. He learned to sail in dinghies at YMCA camp in North Carolina and went on sail other small boats through his high school and college years.

In 1987, Rick moved to Hilton Head Island, SC, and began teaching sailing at Island Water Sports, South Beach Marina. He taught on 19' Flying Scots and J-24's. He also sailed various other larger sailboats.

In the early 1990's, Rick became a USCG-Licensed Captain and began work as Captain of the Sailing Yacht "CHEERS" a 47' Morgan Nelson-Marek day-sail boat located at Harbourtown Marina. Rick worked as a Captain on this boat for several years and during this time made his first charter trips in the Caribbean.

Rick fell in love with Caribbean sailing and has continued to organize charter trips nearly every year since the early 1990's. He has sailed extensively in the British Virgin Islands and The Grenadines as well as St. Martin, St. Barts, Statia, Guadeloupe, Dominica, The Saints, and Belize.

Rick enjoys not only the work of sailing but also the people who sail with him. Rick teaches, entertains, and inspires his crew along the way as they sail to beautiful and exotic locations.

Our Policy

We invite everyone to Sail With Captain Rick.

We do not discriminate on the basis of race, creed, color, nationality, religion, gender, or sexual orientation. However, we strive to assemble compatible and congenial crews generally attempting to build trips from groups of people with similar interests and backgrounds.

Our personal interest is in being ecologically sound, instructive, and inspiring. We do not tolerate drunkenness or inappropriate behaviour. Come to enjoy the beauty of the islands, the pleasure of the sailing, and the friendship of the people.

We enjoy family groups and work well with children (suggested age for sailing cruises is six year-olds and older who know how to swim). We are comfortable with a variety of lifestyles and interests. Feel free to communicate if you have any concerns.