Southern New England - 4 day Itinerary
Day One 0900: Depart Newport 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 luncheon 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.
Day Two 1000: 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
reknowned 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 tranquillity.
Distance 35 miles.
Day Three 0930: 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.
Day Four 1030: Today we depart Cuttyhunk and head westwards again, back to Narragansett Bay and Newport. Depending on the time available a nice luncheon 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.
Southern New England - 8 day Itinerary
Day One 1200: Depart Newport for Block Island - Great Salt Pond - Distance 23 miles.
Day Two 0900: Block Island to Martha's Vineyard - Edgartown Harbor, via luncheon stop at Tarpaulin Cove - Distance 60 miles.
Day
Three 1000: Edgartown to Nantucket - Distance 25 miles.
Day Four: In Nantucket.
Day Five 1000: Nantucket to Woods Hole - Hadley's Harbor - Distance 33 miles.
Day Six 1030: Hadley's Harbor to South Dartmouth - Padanaram Harbor, via luncheon stop at Quick's Hole - Distance 20 Miles.
Day Seven 1200: Padanaram to Cuttyhunk - daysailing on Buzzards Bay offers many choices, depending on wind and weather - Distance, straight line, 12 miles.
Day Eight 1000: Cuttyhunk to Newport - Distance 25
miles.
