Newport, Padanaram, Cape Cod, Woods Hole, Nantucket

Themes: Chic/Exclusive, Family, Historic/Ruins, Romantic/Honeymoon,

A great tour of the famous South Eastern New England Sailing Destinations. This Charter offers Whaling and Sailing History, Dunes, New England Mansions and culture.

See the sites of the famous sailing town of Newport

Itinerary provided with great thanks to Ian Fagg (SV Extraordinary)!

Newport Rhode Island is an excellent place to start your charter because of the large number of charter boats and moorings, excellent provisioning, historic town, and sailing culture.  It is a true sailor`s port, especially since the US Navy left 35 years ago, increasing the beauty and sophistication of the town.

Before you go, you might want to rent a bike and take the scenic 10 mile tour along Ocean Drive for a beautiful coastline tour. Stop off at Castle Hill Hotel and Restaurant for lunch or refreshments.  Most of the mansions are located on Bellevue Avenue on the way out to the Ocean Drive.

The Cliff Walk is a three mile path along a rocky coast that provides a back lawn view of the mansions on Bellevue, or you might want to take a guided tour of any one of the numerous mansions.

Newport`s yachting history is preserved in the Museum of Yachting located in Fort Adams State Park.

The International Tennis Hall of Fame and Museum is located in the historic Newport Casino - the site of the first national singles championship in 1881. 


Padanaram, South Dartmouth

Newport to Padanaram - 27 Miles

This is an excellent first sail for those who want to move out of Newport on day one.

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 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.

Through the Cape Cod Canal to `P`Town`

A 48 mile, 6 hour sail through Buzzards Bay, the Cape Cod Canal through Cape Cod Bay to the end point 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 stip 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.

Provincetown is 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!


Cruise the Atlantic coast of Cape Cod all the way to historic Woods Hole

43 Miles or about 5.5 hours sail

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 too 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.  Yankees Fans are advised to keep a low profile, as this is Red Sox territory. Games will be on in most every bar, restaurant and public place and baseball hats with a "B" are everywhere.  There are some great sailors bars in Woods Hole. 

There are some fascinating excursions hosted by the Institute if you want to learn more about marine life.  There are also many exclusive mansions, 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!


Sail through Nantucket Sound to the exclusive island of Nantucket

Nantucket is an island with roots in the Whaling and Fishing trades.  It has become an exclusive refuge of the rich and famous from New England and New York.

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 Augut, 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 Bass and Bluefish) are one of the most prevalent leisure choices in the town.  You will find an unrelenting number 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.

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

26 Miles - 3-3.5 hours


A recent storm took out the southern sand bar entering Edgartown, allowing the tidal current to flood back and forth through the channel at up to 5 knots.  Moorings have consequently become limited.  Anchoring outside is fine as long as the wind is not strong from the North.

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 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 are Vineyard Haven, a scenic town that also offers an antique merry go round - which the kids (and alults) will love.

Cruise through the Elizabeth Islands

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 casaul dining at a reasonable price and with panaromic views of the Vineyard Sound.  There is also a nice bakery in town.

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.

Yacht Charter

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