A landlubber's guide to sailing

By Katy Plasse
Published: July 30, 2009

One of the many joys of spending the summer on the Vineyard is the tantalizing opportunity to step from the safety of land aboard one of the countless sailboats bobbing in its harbors - and to take advantage of what many consider some of the best sailing conditions in the world.

Captain Greg Coogan at the helm of Welwyn, his 30-foot Alden gaff-rigged sloop. Photo by CK Wolfson

But for some, the idea of setting sail is met with hesitation. Even locals who grew up surrounded by the ocean may not know the first thing about being aboard a sailboat. What should one wear? What should one bring and leave behind? Where's the safest place to sit as to not be flung overboard?

But these uncertainties should not be cause to miss out on the beauty that is the Vineyard as seen from the sea. It's an amazing blend of peace and power when the sails are raised and the motor is shut off, and the you feel the boat come to life under you, nearly silent, powered solely by the wind. Because, even Ahab had a first time at sea.

Captain Greg Coogan, a math teacher at Tisbury School and Chairman of the Oak Bluffs Board of Selectman, owns and operates Welwyn, a 30-foot Alden gaff-rigged sloop. He's been sailing Vineyard waters for more than 40 years and he says taking people sailing for their first time is one of his favorite experiences.

"I especially love taking out people who have lived on the Island their entire lives, but never seen it up close from the water, except from the ferry," Mr. Coogan says. "It is really nice to see the Island from another angle. It's quite peaceful and very exciting."

Adding that his preferred time to sail is afternoon or early evening, when the wind is relatively calm, Mr. Coogan says, "It's a much smoother ride and there are fewer boats on the water. Also, the colors are beautiful at that time of day, muted and stark. It shows people sailing can be comfortable, and a lot of the time, that is what you are going for."

Being comfortable also dictates what one should wear on a sailboat. A "pleasure cruise" should be exactly that: pleasurable. Mr. Coogan recommends wearing layers, because although it may seem like a scorcher on land, it can be chilly on the water, especially on an evening sail when the sun is setting.

Teresa Carey, captain of the 37-foot wooden schooner, Valora, agrees. She recommends bringing lots of layers and, even on a seemingly sunny day, a waterproof jacket (known as foul-weather gear among sailors), as weather can change quickly at sea. Valora (valoracharters.com) can be booked for private charters and day sails out of Owen Park in Vineyard Haven.