Cruising Most Commented

A century ago, 300 individual communities dotted the islands of Penobscot Bay, Maine, each independently thriving off the land and sea. Today, the town of Rockland is one of 15 remaining communities, and it takes its role of culture-preserver seriously.


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Boat shows are the ideal place to scratch your sailing itch. There, you can see what’s new in boats, gear, electronics and apparel, all while being surrounded by like-minded sailors. However, it’s rare you actually get to go sailing at a boat show, much less learn to sail. 


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An Englishman I met in British Columbia once told me that sooner or later every sailor falls in love with an older woman. His name was Duncan, and the moment he saw my boat, Drummer, he was awash in longing...


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We have an inflatable globe that hangs in our saloon, and it is ruining my life. It is an innocuous-looking thing: the different countries are decked out in cheery purples and oranges, and a there’s jagged Sharpie line showing our route from the Chesapeake to the South Pacific. But somehow, whenever talk turns to the future, the globe jumps off its perch and into someone’s hands. Mesmerized, we turn it and turn it, trying to take in every country, every possibility, every tiny harbor. And we begin to play an endless game of And Then We Could.


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How and why one sailor went from bluewater cruiser to creek crawler


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