Schooner Eastwind charts familial course in Boothbay Harbor

Posted June 28, 2014, at 7:04 p.m.

BOOTHBAY HARBOR, Maine — The schooner Eastwind travels eight knots into a headwind. At the helm, Herb Smith quietly charts a course for Burnt Island.

“Take that tight in Doris,” he calls out to his wife as the 65-foot vessel glides peacefully out to sea.

From the bow, their son Tom scrambles back to assist.

It’s another day at sea for the Smiths, who have been charting schooners on Boothbay Harbor since the early 70s. During that time, the couple have owned and built six sailboats, three of which they crafted by hand from wood.

The history of this seafaring family is similar to this sea-girt town where English fishermen settled in the mid-1600s. The self-proclaimed “Boating Capital of New England” has been their sailing home for decades.

As the Windjammer Days Festival heralds the start to summer this week, schooners from the Penobscot make their way into Boothbay Harbor with majestic sails unfurled. Docked on Pier 6, The Eastwind, built in 1999, is the newest in the Smith’s small fleet.

Tom, who sailed around the world twice with his family, purchased the charter with his wife Jennifer six years ago, thereby extending the tradition for another generation. This summer Herb, 73, is back as captain.

Making his first sailboat at age 13 and teaching himself the hard way, on a sailfish in Old Orchard Beach, the former Disney cinematographer is a classic do-it-yourselfer.

Looking out to sea and pointing out a seal and later a porpoise, he is clearly at home at the helm. What is it about sailing that buoys his spirits?

“You can get on a boat and you can escape. You think all your problems are gone, except you bring them with you,” said Herb. “It’s an adventure, it’s a dream.”

That adventure began when the couple met 44 years ago, and their love of sailing bloomed.

Herb convinced a master boat builder in Portsmouth to teach him to build a schooner. The couple got married on their first boat, the Appledore 1. But that ship almost didn’t sail.

“He broke up with me once because he said he had no time for boat building,” said Doris, a Kittery native and daughter of a lobsterman. “If we were going to be together, it was all about the boat.”

To cement the bond, she became a skilled shipwright and able sailor.

“He’s the captain, I’m the crew,” she said, lowering the boom.

They have written two books about their adventures, “Sailing Three Oceans,” and “Dreams of Natural Places.” The books log and chart their trips with photos of a more innocent time of travel.

“There is a subtlety to it, in the balance of forces that are engaged when a schooner is sailing. It’s moving entirely by wind with the ballast and the hull keeping it in check,” said Tom, 37, whose sisters also circumnavigated the globe. “Everything is sensitive to the wind and the angle that you are at and your destination.”

Though dreamlike, living on a boat was not always peaceful. The family had to worry about rogue waves, white squalls and pirates.

“[But] they weren’t pirates with guns,” said Doris, as they are today.

Many times money was tight, they bartered canned ham and clam chowder with natives in the tropics for fruit.

One time, off the coast of Africa, they had to sell their boat for a down payment to make it back to Maine.

“We were young and ignorant. When you are young, you don’t realize it was that hard. Today, knowing what I know now, I wouldn’t do it. It was different back then. It was a different world,” said Doris. “The oceans were virtually empty because people weren’t doing trips back then.”

They favor Boothbay Harbor for its rich and varied scenery. But they have rounded Cape Horn and know firsthand what the sea can do.

“Out there is a lot different,” said Herb, pointing to the mighty Atlantic Ocean beyond the bay. “It’s like going over Niagara Falls in a barrel. Everyone gets seasick, even me, but you get used to it.”

Fast forward four decades and the family intends to continue the legacy.

The schooner Eastwind sets sail four times a day from its dock off Commercial Street. Two-hour tours thread among the inner and outer harbor islands.

On a good gust of wind, Tumbler, Mouse, Squirrel and Burnt islands come into view. The white oak and cedar schooner, modeled after a Gloucester fishing vessel, is also available for six-hour trips.

“It’s a very lovely story. We hope we can keep the business alive for as long as possible,” said Jennifer Smith, who left a career as a business consultant to keep Eastwind forging ahead.

“They have had a fantastic life,” she said. “They have persevered; they have made their own path.”

For information about the schooner Eastwind, visit