Paradise Connections Yacht Charters Sample Itinerary for 7-night New England Crewed Yacht Charter Sailing Vacation

Destinations & Sample Yacht Charter Itineraries

New England: 7-night crewed yacht charter sailing itinerary

by Tom Rowe

MAP of New England

Day 1

Sail to Block Island, Rhode Island. This is approximately a 3 to 4 hour sail depending on the weather. A beautiful island – a nice place to rent bicycles or mopeds and explore. Go to the Mohegan Bluffs and enjoy the view.

Day 2

Sail to Edgartown, Martha's Vineyard. Edgartown has become a fashionable summer enclave for upscale city folk looking to be close to big water when the hotel season starts its engine. It's an old fashioned looking village whose narrow and leafy streets are fringed with gracious historic homes named after their original, seafaring owners. Sailing is a passion here. In mid-July the Edgartown Yacht Club sponsors the modestly-if not definitely-week-long race named "The Regatta". The ocean sailing competition (open to the public) draws more than 100 boats that range from 19 feet to 60 feet.

For those not up to such a tasking challenge, the village is thronged with beaches. Lighthouse Beach is off the entrance to Edgartown Harbor, to starboard; and between Oak Bluffs and the village is the state beach, running for two miles. Both beaches, as you might well expect, get very crowed during the summer.

On Chappaquiddick Island, between the other beaches, is the Cape Pogue Wildlife Refuge. Summer people aren't crowds in this area, so it's a fine place to lose yourself if you're up for an invigorating, scenic hike.

On the mainland - the main island, that is - is another choice hiking ground, especially if you're an avid birder. The Felix Neck Wildlife Sanctuary is a 200-acre tract owned and operated by the Massachusetts Audubon Society. By the summer the nature trails are ripe with wild blueberry, blackberry and beach plums.

Rent a bike and visit the beaches at Gay Head where you can take a clay bath.

Day 3

Sail to Nantucket. You may want to spend a few days here, if you can. Nice shopping, wonderful restaurants and a lovely island.

Rising 100 feet above the sea, Nantucket is fifteen miles long and lays three miles wide at its widest. It is amazing how busy it gets on a dot of land in the Atlantic.

Although there are a surprising number of cars, most people rely on bikes or mopeds for transportation. Nantucket, as you might expect has a great deal to offer in the way of interesting historical sights, and finding your way to them in this town of shaded side streets should prove to be equally enjoyable, if not outright adventurous.

Undoubtedly, one of the more popular stops is the Whaling Museum on Broad Street, just up from Steamboat Wharf. Originally a factory for refining Whale oil, the museum has all the tools of the trade, as well as a full-sized whale skeleton, a whaleboat, and an unparalleled collection of scrimshaw. Lecture tours of the exhibit are offered also.

Besides the shops and galleries that jam the town, fishing charters are one of the most prevalent leisure choices in this town. You will find an unrelenting number of operations to choose from at Straight Wharf.

Swimming and surfing are, of course, favorite activities, and most of the beaches are pleasant for both-particularly Surfside and Nobadeer beaches, while the waves at Sconset can get dangerous. Cisco is a narrow, hence less popular and less crowded.

But being bicycle bound you may also want to explore what the wilder portions of the island have to show you. The picturesque bike paths are outlined clearly. The area is protected by the Nantucket Conservation Foundation which owns more than 7,700 acres of land, chock full of deer, marsh hawks, and the rare broom crowberry.

Day 4

Spend another day in Nantucket.

Day 5

Head to Woods Hole. What's nice about visiting Woods Hole-assuming you can find a place to leave your boat-is that the town, though crowded, is compact and everything can be reached on foot, especially from Eel Pond, at the heart of the village. From the entrance to Eel Pond, at the Water Street Bridge, we'll take a clockwise tour:

Depending on the time of year, you may see one of the 125-foot schooners, the R/V Westward and R/V Corwith operated by the Sea Education Association (SEA) tied up at the main wharf, as you head west on Water Street.

The Community Hall at the Water Street Bridge is a century-old building where you'll find a bulletin board of current events in town. A couple of blocks west is the Yalden Sundial, which, it's claimed, is accurate to within 30 seconds. Here you can synchronize your crew's watches and get a great view of Woods Hole Passage and the Elizabeth Islands at the same time.

Nearby, to your right on the aptly named MBL Street, is the privately operating Marine Biological Laboratory. Limited tours of the laboratories themselves are available with prior arrangements. At the end of Water Street is the popular Woods Hole Aquarium next to the entrance to the National Marine Fisheries Service facility. It's home to 150 species of sea life and a lively pool of Atlantic seals who are always a big crowd-pleaser – particularly at their two daily feedings.

Day 6

Sail to Cuttyhunk. Cuttyhunk is the most populated of the Elizabeth Islands, and the only one that has a year round community-albeit only 40 people. Many of the families have been here for generations and make their living from the fishing or the tourism industries, which increases the population to about 400 people during the summer. The nearly self-sufficient community shares the island (2.5 miles by 0.75 miles) with deer, rabbit, muskrats, and pelagic seabirds. The waters off Cuttyhunk are superb fishing grounds for striped bass, many of which have been logged as world records.

Cuttyhunk is a dry island (meaning no liquor is sold there), so you'll have to bring your own thirst-quenchers if you want something strong to drink. The Allen House offers casual dining at a reasonable price and with a panoramic view of Vineyard Sound. There's also a bakery in town (sensibly called the Bakery) that serves breakfast and lunch items along with pastries and other goodies.

Day 7

Return to Newport in the morning.

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.

Go To Top

HOME > Destinations & Sample Itineraries > New England: 7-day charter