Sailing Where the Wind Blows: Chartering

This sailing club travels light and goes where the wind blows.

Going where the wind blows and, more importantly, where we can get charter sailboats! The Sailing Club, Inc. owns no property, no boats, no building, not even a gavel! We rent what we need and have traveled all over the world utilizing safe and well-maintained sailboats as bareboat charters.

Jack Buckley, late member of The Sailing Club, Inc.
The late Jack Buckley sailing with Old Glory flying in the background. Buckley was a member of The Sailing Club, Inc. which charters boats in a wide variety of locations.

Our own club-trained and certified skippers and first mates work with crews of five or six people, teaching them what they may not know and encouraging those who know how to sail. Every trip is a chance to learn new skills or improve old ones.

Over the years our club members have sailed in the Chesapeake Bay, the Netherlands, France, England, Canada, multiple islands in the Caribbean, the Great Lakes, Maine, Hawaii, and the Outer Lands of New England.

Our club members are varied. They come from different backgrounds and different boating experiences, but they have two things in common: they know how to get along with others and are willing to learn new skills. Often our club members are folks who have sailed in the past but have been away from it for a while. Others have never set foot on a sailboat but really want to learn. Those that stick with the club-provided training reap wonderful rewards.

Sharing space on a 42- to 46-foot sailboat is not everybody’s cup of tea. However, most club members find that after the first night, things get a lot easier. The camaraderie created as part of a crew working on daily tasks has a way of smoothing out any rough moments. Likewise, celebrating a successful sailing afternoon while at anchor or at a dock with your crew creates good memories and lots of photos.

Learn more details at

By Mary Ann Gordon

Charter Directory

Chartering articles