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The Perfect Off Season

On the first day of our charter we sailed to Cuttyhunk, Massachusetts, a charming island at the tip of the Elizabeth Islands between Vineyard Sound and Buzzard’s Bay. We dinghied ashore and bought fresh cod from a fisherman whose wife had lived on Cuttyhunk her entire life. We moseyed on to a general store, where Jaci, one of our crew, bought the Sunday Times and cut out the crossword

On the first day of our charter we sailed to Cuttyhunk, Massachusetts, a charming island at the tip of the Elizabeth Islands between Vineyard Sound and Buzzard’s Bay. We dinghied ashore and bought fresh cod from a fisherman whose wife had lived on Cuttyhunk her entire life. We moseyed on to a general store, where Jaci, one of our crew, bought the Sunday Times and cut out the crossword puzzle.

The four of us on the trip, Matt, Tyler, Jaci and I, met through college sailing. Matt and Ty and I were teammates at Northwestern and Jaci sailed for Notre Dame, but we’d endured enough Midwest regattas, waiting for the wind to blow or the ice to melt, to graduate with close bonds. Now trying our luck at the real world—the gals in Boston and the guys in Chicago—we were eager to reunite doing what brought us together in the first place: sailing.

Jaci’s little puzzle was our companion for the rest of the trip. It sat on the mahogany dining table of the Jeanneau 54DS we’d chartered from Bareboat Sailing Charters out of Newport, Rhode Island. Between quiet marinas, spectacular sails and idyllic towns, we’d gather around and scratch our heads, willing more answers to come. Slowly, they did. As the little white boxes filled up, so too did the memory cards on our cameras as we discovered the delights of sailing through an Indian summer in New England.

Welcome to the Club

“I’m warning you,” said Brian Blank of Bareboat Sailing Charters as he introduced us to the boat, “once you spend a week on this gal, sailing will never be the same again.” The first time we saw Club Carp was at Fort Adams State Park, where she was docked at the most convenient spot possible—adjacent to a parking lot and minutes from the open sea. Club Carp, or “The Club” as she came to be affectionately known, was a classy broad. Belowdecks, she sported white leather coaches, a well-equipped and spacious galley, a comfortable nav station and three full heads (plus a fourth shower). The aft stateroom had enough storage and sleeping space to make you forget you left home.

Underway, she sailed with a grace that shone in heavy winds, but at 55 feet long and 16 feet wide, she was a little intimidating. Over time, the bow thrusters and powered winches helped us settle in and we found her a joy to sail. At times, she even made us swoon.

As soon as we cast off from Newport and sailed east toward Cuttyhunk, Matt at the helm, The Club locked into a sturdy September breeze. That first afternoon on Cuttyhunk was warm and sunny and allowed us to explore the small community thoroughly, not that it took very long. Cuttyhunk is one big hill with one winding road, one school, one church and a year-round population of around two dozen souls. As we walked up the hill, we passed by weathered-shingled houses with white trim, each one built in the fashion of a sleepy fishing town. Up and over the hill we discovered a striking view of the sun setting on Gosnold Monument, which we watched from some abandoned World War II bunkers, now overgrown with tall grass. Back at The Club in Cuttyhunk Pond, we dug into the local cod, each bite fresh and satisfying.

The next morning we sailed through Quicks Hole for Menemsha, a fishing village at the southwestern end of Martha’s Vineyard. Temperatures were in the high 70s, so Matt rigged up a halyard swing and we leapt off the bow pulpit and swam ashore for some beach volleyball, finding it hard to believe it was actually September. Menemsha is a quintessential fishing village, where lobster pots and buoys are perfectly acceptable landscaping pieces. The shops and restaurants are quaint, and in the evenings a modest crowd gathers on the beach to applaud the beautiful sunsets.

The Joys of the Off Season

Martha’s Vineyard, Block Island and the islands in between are well-loved New England attractions, but visiting these tourist havens in high season can be a double-edged sword: the weather, cuisine and sight-seeing are prime, but so are the crowds. When Blank arranged our charter for the last week of September, he couldn’t have chosen a better time, as we got the best of both worlds. Most shops and restaurants were still open (though many were closing within the week) and not a day went by without a thorough sun-soaking. It felt like summer had never ended.

Indeed, save for the lack of other tourists, it hadn’t. From Menemsha we had a beautiful sail around the northern shore of the Vineyard to Oak Bluffs, with The Club cutting through the waves under a cloudless sky. Over the next three days we enjoyed a grand exploration of Martha’s Vineyard, an island that was born to be vacationed on. Here the shopping, restaurants, bars and beaches are second only to the spectacular sailing.

To see everything this nautical community has to offer, it’s best to rent a car. We took one out of Edgartown where Doris Clark, a Vineyard native and president of marthas-vineyard.com, came along to give us a tour. En route to Gay Head lighthouse, an iconic landmark, we stopped at the Orange Peel Bakery, where two native Wampanoag cousins baked us fresh oatmeal cookies from a stone oven. We purchased them on the honor system—picking what we wanted and putting what we owed in a bucket while the two cousins stayed busy with their ovens out back. Every Wednesday, the bakery hosts a pizza party where visitors and locals provide a potluck of toppings and the bakers provides the delicious crust, all of which is enjoyed while swapping stories around the fire.

In Oak Bluffs, we discovered a mesmerizing place: Martha's Vineyard Campmeeting Association, a collection of multi-colored cottages with intricate trim and well-manicured lawns packed tightly around a massive tabernacle. The community was created in the 1830s when families began staking out the same camping spots year after year for their annual Methodist revival meeting. Eventually they began building the cottages, which they painted outrageous colors and passed down to their children. Clark explained that almost every house in the campground has been in a family for generations, and that even the most modest ones now sell for around $1 million.

That night, we had a fantastic dinner at Coop de Ville in Oak Bluffs, where we enjoyed delicious lobsters while seated at a picnic table in the sand. The open-air dining room had a beach bar feel, but with five-star cuisine, and the service was great. After dinner, we stumbled upon a saxophone player in the streets and Tyler convinced us to join in the impromptu dance party that had gathered around him.

We topped off our Martha’s Vineyard experience with a day at South Beach, a bike ride around the island and a fantastic encounter with the Edgartown harbormaster, who has one of the friendliest faces on the Vineyard.

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