Destinations & Sample Itineraries
New England: 4-night yacht charter sailing itinerary
by Tom Rowe
Depart Newport at 9am for Martha's Vineyard. Sailing out the scenic East Passage of Narragansett Bay and then turning east, along Ocean Drive, you will pass a number of the grandiose "Summer Cottages" which proliferate along the waterfront. Depending on the weather there are several delightful lunch stops available in the Elizabeth Islands. The pristine beach and protected anchorage at Quick's Hole on Nashawena Island is a favorite. After a leisurely swim and lunch, continue on past Nobska Point and West Chop to Edgartown, where you will arrive in the late afternoon. The protected anchorage, moorings, launch service, facilities ashore and classic New England atmosphere of the town make Edgartown a must see destination on everyone's itinerary. This would be a good night to dine ashore as the variety of restaurants available is extensive. Distance 55 miles.
After a relaxing breakfast aboard set sail for Tarpaulin Cove on the South shore of Naushon Island, another of the classic picnic stops in the Elizabeth Islands. A brisk afternoon sail across Buzzards Bay brings us to Padanaram Harbor, home of the New Bedford Yacht Club and the world renowned Concordia Yacht Yard. There is limited shopping ashore, yet the center of town is but a short walk from the launch and who knows what treasures may be found. Dinner this evening is definitely aboard, where you will enjoy the chance to view the sunset in unsurpassed tranquility. Distance 35 miles.
Another leisurely start to the day has us setting sail for Woods Hole and Hadley's Harbor. This is an easy sail and allows us to enjoy the prettiest harbor within 100 miles; but, we must get there early as there is limited anchoring space available inside. After lunch the Sou'wester usually perks up and it affords us the opportunity to have a spanking sail down the bay to Cuttyhunk, a quaint island village, at the western end of the chain separating Buzzards Bay from Vineyard Sound. Going ashore you will be struck by the feeling that you're going back in time to the turn of the century or before. Cuttyhunk has several inns where the dining is family style and concentrates on the wholesome, simple specialties of New England Cooking. Distance 35 miles.
Today we depart Cuttyhunk and head westwards again, back to Narragansett Bay and Newport. Depending on the time available a nice lunch stop is at Third Beach in Middletown, a few miles up the Sakonnet River, back in Rhode Island. If we're pressed for time and a stop isn't possible, we should be back in Newport no later than 2:00 in the afternoon, having had a brief glimpse of the best that Southern New England has to offer. Distance 25 miles, nonstop.
Remember, there are many variations to this sample itinerary. Your charter will be customized to fulfill the dreams of your charter party. That's the beauty of a crewed charter yacht sailing vacation.