The Boston Bon Vivant

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Sailing on the Adirondack III

There is no better way to while away a gorgeous summer evening than setting off to sea at sunset aboard a classic wooden schooner.  As the sun dips below the horizon and her wind-filled sails carry you forward, you'll be transported back in time to a long-ago era when hundreds of tall ships, brigantines and sloops dotted the Massachusetts coastline.


During the years before the American Revolution, Boston was the premier shipping and trading port in North America, and hundreds of tall ships brought supplies in and out of her harbor on a continual basis.  Today, historic schooners such as the Adirondack III still cruise the harbor, offering locals and visitors alike the chance to experience turn of the century yachting while taking in the spectacular views of the city's modern skyline. 

Although we have lived here for fifteen years, we never tire of the opportunity to leave everyday life behind for a few hours and enjoy the simple pleasure of sailing on the open sea.  Day, sunset and evening sails are offered daily from May through October 16th.

Measuring 80 feet in length, the Adridontack III is modeled after 1890s style pilot schooners.  An all-wooden vessel with a white glass overlay hull, she boasts mahogany rails, two towering Douglas Fir masts and nearly 2,000 square feet of sail. 

When traveling by air, land or sea, this Saint James dress is my absolute go-to; it dries quickly, is UV-resistant and unfailingly refuses to stain, shrink or wrinkle.  Pairing it with a navy skirt and grey blazer makes it office appropriate by day, and I can go from the boardroom to the boathouse without skipping a beat!


We've gotten to know the crew over the years, and First Mate Brennon is always kind enough to let me sneak on to the bow and help set the sails!

Built as a working replica of an 1890s coastal schooner, the 67 foot Liberty Star also offers a variety of sailing cruises on the Boston Harbor.