There’s a reason New England sailors are so dedicated; New England is simply one of the world’s best cruising grounds. The southern side of Cape Cod and its off-lying islands—Nantucket, Martha’s Vineyard, the Elizabeth Islands and Block Island—are a cruiser’s dream. The weather is usually benign, there is almost always a sailing breeze, there are plenty of anchorages and, in a cruising area encompassing Rhode Island’s Narragansett Bay and Mystic in Connecticut, there is plenty to do ashore.

Leaving Newport early one sunny June morning, we sailed close-hauled past the shoreside mansions and then eased sheets as we passed the Benton Reef buoy. Reaping the blessings of a good breeze and a fair current, we were relaxing on a mooring in Cuttyhunk by early afternoon—and lunching on oysters and clams, thanks to the Raw Bar boat that you can hail on the VHF.

Another beautiful day of sailing, averaging 6 knots in a mild southwesterly, saw us anchored in Vineyard Haven the following evening and dining ashore. Next day we rented bikes and spent a happy few hours pedaling around the island. That night we discussed the possibilities for the remaining four days of our charter and, with northeasterlies in the forecast, the vote was unanimous—we would depart at dawn and take advantage of fair current and a following breeze to head for Block Island, 45 miles away.

Block Island’s Great Salt Pond is well sheltered and through the boat shied to the gusts next night like a skittish horse, she was snug on her mooring. After that, with the week was nearly over, we elected to spend the next two nights in Narragansett Bay, one in Wickford and one in Newport, before reluctantly handing the boat back.

I’ve sailed this area many times since, but the memories from that first experience are still vivid and help to pull me back there at least once every summer.

AT A GLANCE

Getting there: With T.F. Green airport close by in Providence, RI and Logan Airport not much farther away in Boston, the area is extremely easy to get to.

When to go: The season starts in mid-May, though New Englanders count themselves lucky if their boats are in the water by Memorial Day. September is my favorite month for New England sailing; the crowds are gone, and the weather is still good.

Where to go: Cuttyhunk, Martha’s Vineyard, Block Island, Newport.

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Check out the whole article at https://www.sailmagazine.com/charter