7 Day Sailing Itinerary for Newport RI, Cape Cod, Nantucket and Marthas Vineyard

Rose Island

A 7-day sailing itinerary for Newport, Cape Cod, Martha's Vineyard, Nantucket and Cuttyhunk

A yacht charter starting from Newport offers a large number of charter yachts, plenty of moorings, excellent provisioning options, the historic town, and sailing culture. Newport is also renowned, of course, for the mansions built by many of America's leading families and for providing an insight into the sailing history of the USA. The below itinerary will allow you to explore American history and allow you to get the taste of America whilst exploring some of the wealthiest areas in the USA.

Follow our itinerary and sail to Martha's Vineyard, known as the Jaws filming location, the beautiful city of Boston or dine in some of the best restuarants on the Hamptons. The Hamptons is home to gourmet restuarants, bars, designer stores and many hikining and picknicking destinations. Be sure to go whale watching in Wetherill State Park during your yacht charter!  

Here at Boatbookings, we know everything there is to know about chartering in Newport and our team of brokers are full of knowledge about the local area! 

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Day 1 - Newport - Christie's Landing 

Embark on your boat and spend the evening in the restaurants in downtown Newport. Before you embark on your charter yacht, you might want to hire a bike and take the scenic 10 mile tour along Ocean Drive for a beautiful coastline tour. A good place for lunch along the way is the Castle Hill Hotel and Restaurant. Most of the mansions are located on Bellevue Avenue on the way to the Ocean Drive.

The Cliff Walk is a nice 3 mile path along a rocky coast that provides a rear view of the mansions on Bellevue. You can take a guided tour of many of the numerous mansions there.

The Museum of Yachting is located in Fort Adams State Park and exhibits much of Newport's storied yachting history.

Day 2 - Newport to Padanaram - 27 Miles

Newport itinerary 

Leaving Newport and heading to Padanaram, a village located in South Dartmouth, is an excellent first sail.

There are moorings in Padanaram for boats up to 60 feet which are sold on a first come first served basis, although anchoring out a bit further is generally perfectly fine.

Padanaram is a very pretty harbor and a nice place for dinner aboard. There is a yacht club and a launch service available to boats both on anchor and on moorings.

Day 3 - Through the Cape Cod Canal to "P'Town"

Today get ready for a 48 mile, 6 hour sail through Buzzards Bay, the Cape Cod Canal through Cape Cod Bay to the tip of historic Cape Cod.

Sail north to the top of Buzzards Bay, past New Bedford and to the canal. On the East is Cape Cod - North Falmouth, an excellent destination itself if you have time. As the bay narrows you`ll ultimately arrive at the mouth of the Cape Cod Canal.

The canal is a good place for lunch as you pass through this strip of water that separates the mainland of Massachusetts and Cape Cod.

Provincetown offers moorings or anchor. It is a well protected harbor from any direction.

There are lots of Whale Watching tours in Provincetown, where they guarantee sightings. You may also want to visit the Whydah (Pirate) Museum on the MacMillan Pier, especially if you have children!

Provincetown is known as the gay capital of the north east. By night you will find cabarets, side shows and music. Less open minded guests might take an early curfew, but a lot of fun can be had in this town, whether straight or gay!

Day 4 - Cruise the Atlantic Coast of Cape Cod all the way to Woods Hole

cape cod

 43 Miles or about 5.5 hours sail. Atlantic swells until you enter Nantucked Sound.

Head from Cape Cod to Hadley Harbor is a beautiful and well-protected anchorage. There are some depth constraints in the harbor, so timing your entry according to the tides may be necessary for boats with an 8 foot draft or more.

It's never very crowded here, and a perfect spot for dinner and an overnight. Woods Hole is a somewhat bohemian collection of scientists (from the world famous Woods Hole Oceanagraphic Institute), blue blood New Englanders, and vacationers. You will also see the constant ferrys to Martha's Vineyard and Nantucket.

There are some great sailors hangouts in Woods Hole. Lobster fans can even take it out, cooked for you, for a good price and take it back to your boat.

This is Red Sox territory - during the summer games will be on in most every bar, restaurant and public place and baseball hats with a "B" are everywhere.

There are some fascinating excursions hosted by the Institute if you want to learn more about marine life. There are also many exclusive mansions you can see from the waterfront, mostly built in traditional New England style, with old cedar clapboards and white trimming around the windows. Understatement is important here, even if the houses are immense!

Day 5 - Sail through Nantucket Sound to the exclusive island of Nantucket

Nantucket is a beautiful, quaint, and still largely undeveloped island with roots in the Whaling and Fishing trades. It has recently become an exclusive refuge of the rich and famous from New England and New York because it offers privacy, understated beauty, fishing and boating, and great summer beach life.

Moorings are available from Nantucket Moorings or you can anchor north of the mooring field. Dockage needs to be booked well in advance for July and August, and approximtely 3 years in advance for July 4th weekend.

Nantucket Town is charming and ageless, with many cute shops. There is a Whaling Museum on Broad Street. It originally was a factory for refining whale oil, and exhibits all the tools of the trade including a full sized whale skeleton and and unparalleled collection of scrimshaw (etchings on whale teeth originally done by sailors to while away the hours).

Fishing charters (for Striped Bass and Bluefish) are one of the most prevalent leisure choices in the town. You will find plenty of operations to choose from at Straight Wharf.

Swimming and surfing are also activities of choice, and most beaches are pleasant for both, particularly Surfside and Nobadeer. The town of Wauwinet, with the exclusive Wauwinet Inn, is also a nice location. Originally called the "Haul over" because whalers could haul their boats from the sea to the bay over the narrow strip of sand, it offers both and Atlantic beach with large waves, and a protected beach on the bay, good for gathering shells and waterskiing.

Nantucket is a great island to tour on bike. You can rent bicycles in the town and follow the well-marked bike paths that are protected by the Nantucket Conservation Foundation. You will see deer, marsh hawks and the rare broom crowberry.

Day 6 Sail to the quaint and `preppy` island of Martha`s Vineyard

26 Miles - 3-3.5 hours

The town is very pretty with its tree fringed streets, shops, boutiques and restaurants. You will see preppy dress everywhere, including the famous whale belts, and at night you will be serenaded in the street by acapella singers from Yale and other New England universities.

Try the Martha`s Vineyard Clambake Company for a clambake picnic done New England style. Note, both "Steemahs" (Steemers) and "Kohawgs" (Quohaugs) are types of clams, spoken in the famous Boston Accent (don`t say the "R"s).

Chappaquiddick Island, across from Edgartown offers the Cape Pogue Wildlife Refuge. It`s not crowded here, so it`s a fine place to lose yourself if you`re up for an invigorating hike. If the name sounds familiar, this is the site of the infamous and tragic Teddy Kennedy car plunge off the bridge.

Alternatively, on the mainland is the Felix Neck Wildlife Sanctuary, a 200 acre tract owned and operated by the Massachusets Audubon Society. In the summer nature trails are fipe with bleberry, blackberry and beach plums.

You may also want to visit the quaint town of Vineyard Haven, a scenic town that also offers an antique merry go round that the kids (and adults) will love.

Boats to charter in Nantucket and Martha's Vineyard offer you an opportunity to experience the individuality of of this area like no other!

Day 7 - Cruise through the Elizabeth Islands to Cuttyhunk

Newport sailing

 Sailing duration: 25 miles or 3+ hours sail.

Cuttyhunk outer harbor is open to any wind from the North but protected from Southerlies. The inner harbor offers complete protection and moorings but is limited to boats of 60 feet or less and a maximum 8 foot draft.

Cuttyhunk is the most populated of the Elizabeth Islands. It is a dry island (no alcohol sold) so bring you own if you want it! The Allen House offers casual dining at a reasonable price and with panaromic views of the Vineyard Sound. There is also a nice bakery in town.

Return to Newport

Leaving early from Cuttyhunk it is possible to be back in Newport by 1 pm. Cuttyhunk to Newport is a 25 mile sail - approximately 3 hours.

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