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Desirable Destination: Massachusetts

Timeless Beauty | June


Quite honestly, I enjoy cruising just about anywhere in Massachusetts during the summer, which is one of the reasons I’ve been doing it my whole life. (I was also born and raised there, but that’s beside the point.) From the quaintness of Martha’s Vineyard and Nantucket to the historic-laden shores of Plymouth (where the Pilgrims landed), Salem (the site of the famous witch trials), and Boston (home of the 2004 world champion Red Sox), Massachusetts offers activities for a range of interests that continue to draw boaters each year from all over the globe.

But if you’re looking for something off the beaten path from the aforementioned tourist-heavy destinations, or if you are just looking for a quick weekend escape, set your course for the Elizabeth Islands and head on over to Cuttyhunk. You’ll feel as though you’ve stepped into a land that time forgot.

“Cuttyhunk” loosely translates to “land’s end” in the language of the Wampanoag Indians, who were the first visitors to the island. It is the westernmost island in the Elizabeth Island chain and has a land area of about one square mile.

Anytime during the summer is a good time to visit, but if you ask me, mid-June is the best. It’s not yet high tourist season, the fish are aplenty, and the weather is as perfect as New England weather gets: warm days, cool nights.

If you want lots of action and a bustling nightlife, Cuttyhunk is not the place. Only about a third of the island is settled; the rest is rolling hills of bayberry and grasses, with deer-strewn paths for hiking and ocean views as far as the eye can see. The island has 59 year-round residents, only a few buildings that make up its “downtown,” golf carts in lieu of cars, and no nightclubs. It has a small beach, a marina, a lighthouse, a handful of restaurants, two small inns, and only one schoolhouse. But the allure of Cuttyhunk is not about having activities or a busy sightseeing schedule. Rather, a visit to Cuttyhunk is more about settling into a state of mind, where doing nothing but curling up with a good book and a glass of lemonade or simply enjoying a warm breeze and views of Vineyard Sound with your family are the things to do. It’s comes as little surprise, then, that the peaceful island’s motto is, “If you can’t relax here, you can’t relax.”


Even so, if you’re looking for on-the-water action, Cuttyhunk delivers: Its nearby fish-laden rips and shoals continue to lure anglers from near and far, especially in June, when the blues are running rampant and striper season is on fire. In fact, Cuttyhunk once held the world record for the biggest sport-caught striped bass until 1973.

A visit to the island wouldn’t be complete without a trip to the famed Cuttyhunk Fishing Club Bed and Breakfast, which, as the story goes, was founded in 1864 by a few members of The West Island Club in Sakonnet Point, Rhode Island, who had become dissatisfied with that club’s regulations and went looking for a new place to start their own fishing club. The establishment is still in business today and offers eight charming Cape Cod-style guest rooms and stunning views of Vineyard Sound.

Whether you visit alone or with the family, whether you stay for a night or the summer, the rustic charm and solitude that Cuttyhunk offers is sure to hold a special place in your heart. It certainly has for me.

Desirable Destinations

January: British Virgin Islands
February: Great Abaco Island / Bahamas
March: Little Harbor Cay / Bahamas
April: Los Sueños / Costa Rica
May: Monaco
June: Massachusetts
July: Washington, D.C.
August: British Columbia
September: Montauk, Long Island
October: Hudson River, New York
November: Half Moon Cay / Belize
December: St. Barts

This article originally appeared in the December 2006 issue of Power & Motoryacht magazine.