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The sparkling waters and stirring breezes of Newport, Martha’s Vineyard, and Buzzards Bay are calling. We’ve reserved two beautiful sloops for a week of sailing, sunning, swimming, and touring one of the U.S.’s premiere cruising areas.

We’ll visit several great harbors. We’ll have some good, long sailing days, and balance them out with a full day on moorings in Edgartown.

We will meet our boats in Jamestown, on Conanicut Island across from Newport on Sunday, August 21st.

On Monday, after a morning briefing with Dream Yacht Charter, we’ll set sail for Cuttyhunk, one of the Elizabethan Islands. Cuttyhunk is the only one that’s publicly accessible, the rest are private property. We’ll take moorings outside the tiny harbor (or a brave skipper can try looking for room inside) and use our dinghies to visit ashore. We can pick up fresh seafood in town, or even order it delivered right to our boats.

Tuesday morning we’re off to Edgartown on Martha’s Vineyard. Edgartown has been a bustling port town for three hundred fifty years. Its whaling roots are evident in the names of the bars and restaurants, as well as at The Carnegie, a museum on Water Street. Edgartown’s launch service starts early and runs into the evening.

Stick with us now – our exact plan for the rest of the week depends on space availability in a couple great destinations where we can’t make reservations until April and May.

On Wednesday, there are two possibilities. We could spend the day on the mooring in Edgartown, which will afford us the chance to take a land tour, enjoy the museum with its limited opening hours, and take advantage of the harbor’s free pump-out boat. Crews can pick from many restaurants for dinner ashore, too. Alternatively, we’ll drop our moorings on Wednesday morning and sail up the coast of Martha’s Vineyard to Vineyard Haven, another one of the island’s amazing port towns. We can anchor, take a mooring, or even rent a slip in one of the marinas for an easy visit to the town. This brings us closer to our final night’s destination.

If we spent Wednesday night in Vineyard Haven, then Thursday’s sail will take us back to Buzzards Bay and the mainland harbor of Padanaram, home of Concordia Boats. We’ll anchor or get moorings and get ready for our return trip on Friday. If we spend all of Wednesday in Edgartown, on Thursday we will sail around the north coast of the Vineyard to tiny Menemsha Harbor, where we’ll spend our last evening.

All of these ports are fantastic examples of New England charm and we’ll have a fantastic time no matter where we go. And finally, always remember that on every trip, weather conditions are the final arbiter of our itinerary choices.

After a great final sail back to Jamestown, we’ll return to our moorings on Friday afternoon. Departure is 9:00 a.m. on Saturday morning, so crews can decide whether to visit Newport for fuel before returning to the mooring, or make an early morning run before final departure.

Our Fleet

Our boats are a Sun Odyssey 410 and a Dufour 430GL. Because of its size, we’ll have eight on the 430, but just six on the 410. The 410 has three double cabins and two heads with sleeping space in the main salon. The 430 has three double cabins and one cabin with bunk beds, sleeping space in the main salon, and two heads. Both boats come with dinghies and they have bow thrusters. Additional boats are not available, and demand for this trip is expected to be high.

SunOdyssy 410

Dufour 430GL

The cost of this trip is $880.00 per person (Skippers and Trip Leader - $451.00, Asst. Trip Leader - $665.00). The price includes charter fees, dinghies, and two nights' slip fees. Provisioning, fuel, pump-out, any additional mooring or slip fees, and other incidentals are additional and will be handled by each boat’s crew. A $100.00 deposit and Release of Liability and Zero Tolerance Form  must accompany your Reservation Form.

Please make your check payable to The Sailing Club, Inc. and mail it, along with your completed reservation and release forms, to Mia McCroskey at the address below. Reservations will be processed beginning April 4, 2022 with a random draw of those received by that date. All reservations received after that date are on a first come, first served basis. A final payment of $780.00 is due on July 7, 2022. The Club’s standard thirty-day cancellation policy applies for this event. As mentioned here, confirmed participants should make their own decision regarding travel insurance.

A pre-trip meeting will be held about a month before the trip, at a time and place to be announced. All crewmembers should make every effort to attend in order to meet your crewmates, plan your meals, and make travel plans.


Trip Leader

Assistant Trip Leader

Mia McCroskey

19 Manor House Drive Apt K12

Dobbs Ferry, NY  10522


Joel Mack

5905 Spruce Mill Drive

Yardley, PA  19067



Please note that sailing conditions are dynamic, that your safety, and that of your crewmates, depends on your good physical health and agility.


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