Five good reasons to weigh anchor and experience the joy of sailing

Imagine it: Sunlight sparkles on the water, the canvas overhead is stretched taut, saltwater sprays up and outward, and the only sound comes from the wind driving you forward across the bay.

A sailboat headed toward the protected harbor of Cuttyhunk.

The joy of sailing lies, in part, in the rich array of sensations to be experienced when you weigh anchor. There’s an aesthetic appeal to exploring Buzzards Bay by sail that can be hard to fully appreciate unless you’ve tried it for yourself. And you should try it.

Sailing is far more accessible than you may realize. There are a variety of clubs and organizations from Falmouth to Dartmouth that offer beginner lessons and access to boats. In fact, the Coalition’s Onset Bay Center offers instructional sessions for children, adults, and families, and it periodically makes our fleet of RS Quests available (for a small fee) to adults who know how to operate the boat safely.

And the appeal of sailing goes well beyond the aesthetics of the experience. People love it for all sorts of reasons. There are at least five great reasons to raise the sail for your first journey, or if you’re already a sailor, to get out on the water as soon as possible.

Totally flexible

Weatherly Dorris and her daughter, Charlotte (at the helm), sailing on Buzzards Bay.

First, sailing can be many different things, depending upon your interest, said Quentin Chafee, the on-the-water program manager at the Onset Bay Center. “One of the coolest aspects of sailing is that it’s not just one thing. It’s very adaptable,” he said. “It’s a sport, it’s a recreational activity, it’s a pretty reliable form of transportation, and it’s even a home for some people.”

A former collegiate sailing coach, Chafee said that many people, particularly children and teenagers, get hooked on sailing by getting involved in organized races at local yacht clubs. Indeed, that was his experience. “I was introduced to racing and that’s where I started falling in love with the sport, working my way up through the junior sailing club. I caught the bug when I started racing and never gave it up since then.”

Location, location, location

The old adage about real estate applies to sailing. Location matters, and we just happen to live in one of the best places for sailing in North America. The bay is perfectly designed for sailors. Its 93 miles of coastline contains more than 30 harbors and coves, offering numerous options for exploring. And important for a sailboat, Buzzards Bay is reliably windy, with a prevailing south westerly breeze

“Buzzards Bay is magical. It really is. You take it for granted when you grow up on it. But when you see other places you see how special it is,” said Weatherly Dorris, who runs the Quissett Harbor Boatyard with her family.

Soak in the serenity

If you’re looking for an opportunity to unplug, you should know that sailing can bring something like serenity. It requires close attention to the environment—the wind, the water, clouds building on the horizon, the shape of the channel ahead and the possibility of rocks and shallows. The realities of the experience take you away from everyday worries about the past and the future by commanding your attention … right now.

“Sailing is one of those activities where you are called to be ‘present,’ paying attention to what you are doing,” said Hilary Vineyard, a member of the Coalition’s Board of Directors who has been sailing since childhood. “There are so many things to experience. It’s like a really good meditation class. To be fair, there are plenty of people out there racing, which is a different experience altogether.”

Savor the sense of freedom

Sails at sunset, as seen on the bay and reflecting on the hull of a Herreshoff sailboat. Photo by Charlotte Dorris.

Buzzards Bay and Vineyard Sound offer plenty of small coves and bays that can be explored in just a few hours, as well as destinations that are suitable for all-day and overnight trips. And of course, you can always go further.

“You get the feeling you could go wherever you want under your own power. If I wanted to sail for a few hundred miles or across the Atlantic,” said Dorris, a former member of the Coalition’s board and the current commodore of the Quissett Yacht Club. “There’s something about sailing that you’re not reliant on fuel. With sailing you delight in the winds that will make your boat go a little bit faster.”

Great with a group

While it’s certainly true that sailing can be a solo pursuit, it’s a perfect activity for a family or group of friends. Vineyard, who has been on the water her whole life, fondly remembers family trips with her grandfather up the Maine coast.

Andy Herlihy, executive director of Community Boating Center in New Bedford, said that the organization’s sailing programs are designed around the relationships between instructors and students. “I really think the biggest factor is our staff and how they approach sailing in a safe, fun way,” he said. “If you make it fun for kids, they eat it up. It’s not necessarily the best sailors who make the best instructors. It’s about the focus on engaging the kids.”

The learning that takes place while sailing goes beyond maritime skills, he said, embracing life lessons about leadership, attention to detail, and teamwork. And it’s not just for kids, he added.

“Sailing is one of those sports where you’re always learning. There’s always something new to be learned,” Herlihy said. “Every time you go out it’s different. One of my coaches growing up would always say, ‘Every time you get in a boat you should learn something.’”


Discover a whole new world out on the waters of Buzzards Bay and Vineyard Sound. Chart your course with our resources on where to go and how to get there.