New England and Long Island Yacht Charter Planning Guide

New England Charter - Quaint Port
A picturesque New England port

About Chartering in New England and Long Island, New York

The combination of Long Island and the famous port destinations in Maine, Massachusetts (Boston, Cape Cod, Marthas Vineyard, Nantucket) Connecticut, and Rhode Island (Newport) in New England provides everytihng from nearly endless and dunes to unbelievably quaint towns to historic ports still resonant from colonial New England and it's Native American heritage and of course world famous lobster.

New England is rugged, spectacularly beautiful and full of history and charm. Its quaint port towns, sandy beaches, romantic islands, small shops and art galleries, and fine restaurants exude understated elegance. There is a long tradition of fishing and sailing that is apparent at every stop.  You won't find a lot of flash in New England, there is a strong link all the way back to the Puritans where ostentation is not the natural way of New Englanders. They would rather let their bounteous land speak for itself, and mesmerize you with all it has to offer.

New England and Long Island Charter Locations

The famous port of Bar Harbor, Maine
The famous port of Bar Harbor, Maine

Maine - Rugged Coastline, Amazingly picturesque towns, Lobster and Blueberry Pie

Winslow Homer spent a good part of his career trying to capture the beauty of the Maine coastline - it can have a mesmerizing effect on you.  The facmous coastline was carved long ago by the ice age glaciers that left behind many inlets and estuaries that can take a lifetime to explore.

Maine mixes understated money well with it's natural beauty, where towns such as Kennebunkport, Camden and Prouts Neck serve as retreats for some of the most famous families in America. Beautiful sandy beaches and quaint fishing/lobster ports are nestled among the rocky shoreline, and you'll take more than a few pictures of classic New England Lighthouses.

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Aerial View of the Boston finanicial center and waterfront
Aerial View of the Boston finanicial center and waterfront

Boston - Freedom Trail, Beantown, Faneuil Hall

Boston from its beginning looked to the sea, and it remains a city where boating is a key part of the culture.  Today, Boston mixes an international outlook with traditions datiing back to its founding in colonial times, and of course its most famous attraction is the Freedom Trail, that takes one through many of the key events and places of the American Revolution.

A Boston stop is almost requisite for any New England Charter, to see Boston Commons, the Statehouse, the Old North Church ("one if by land, two if by sea"), Faneuil Hall and the other key attractions.  Boston offers fine cuisine, great shopping (Newbury Street), and if you're looking for traditional entertainment - try to take in a Red Sox game while you're there.  Sports are a key part of the city's fabric.

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Lovely sandy beaches and houses on the shore at Chatham
Sandy beaches and typical Cape Cod houses on the shore at Chatham

Cape Cod - Boston's understated vacationland

Cape Cod, just an hour sout of Boston, is the area where Bostonians go to get away, and often love it so much they buy their second house there. Cape Cod offers amazing beaches, bass fishing, quaint fishing towns that include Provincetown and island excursions.

Cape Cod is essentiall a long spit of sand, curled northward like a flexed arm. With all that sand, there are beaches everywhere, all with their own aspects and advantages. The west coast offers dramatic dunes and great breakers, where the northern and southern beaches are calm and offer great fishing and massive low tides to explore for shells and sand dollars.

Throughout Cape Cod are famous towns such as Falmouth, Woods Hole, Chatham, and Dennis that have a fantastic New England charm.

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Martha's Vineyard - An island with a timeless, classy feel

While closely associated with and visible from Cape Cod, Martha's Vineyard has its own identity and definitely has in Island feel to it.  The primary port for yachts is Edgartown, which is upscale and offers excellent restaurants and beaches nearby.  Martha's Vineyard is very much about its abundant beaches and dunes, and will lose you in its timeless pace.

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Nantucket lighthouse from a charter yacht
A quintessential New England lighthouse on Nantucket

Nantucket - historic whaling island, vacationland of billionaires

The remote, charming island of Nantucket, a 1-2.5 hour ferry ride from Cape Cod (depending on which ferry you take), has become the place to be for New England's well heeled.  The old whaling town of Nantucket has many quaint, timeless restaurants and shops, with original cobblestone streets and beautiful sea views.  It's a great place to rent a bike and just enjoy the dunes, grasslands, small beach towns and and ice cream cone or two!

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Newport, Rhode Island - historic sailing town

Newport is the original sailing capital of the USA, offering museums, mansion tours and a taste of old New England. It's truly a sailing lover's paradise, and was home of several classic Americas's Cup races.

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Montauk Light, eastern Long Island
Montauk Light, eastern Long Island

Long Island - Sag Harbor and the Hamptons - where New Yorkers come to play.

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New England Luxury and Crewed Yacht Charter Itineraries

A typical crewed charter would focus either on southern New England and Long Island, or northern, which would primarily cruise the Maine Coast

Northern New England

Starting from Boston, you quickly reach the delightful and historic ports along the north shore. Marblehead, Gloucester and Manchester by the Sea are all pretty ports with great New England charm and history. Continuing up the coast, you will briefly be on the New Hampshire coast, and then in to Southern Maine. Classic ports to visit are Prouts Neck (Winslow Homer), and Kennebunk Port (you can see the Bush estate).  Continuing up the coast ("Down East" in the local parlance) you will find Wiscassett, Boothbay harbor and finally Bar Harbor and Mount Dessert National Park. While you are nearly guaranteed to have a day or two of fog along the way, you will be relaxed and mesmerized by the beautiful coastline, enjoy plenty of lobster and seafood, and bring home many pictures of light houses and lobster boats!

Southern New England and Long Island

A southern New England charter normally starts in the historic town of Newport, home to many America's Cup races and some of the greatest American Mansions.  You can cruise across the Long Island sound to the Hamptons and then continue Northeastward to explore the sandy beaches and incredibly quaint towns of Martha's Vineyard, Nantucket and Cape Cod.  This is American beach culture at its finest and you will find many great local shops and restaurants featuring seafood, especially clams, mussels and lobster.  End up by spending some time in Provincetown, which has a culture all it's own and go whale watching and bass fishing on your way to Boston.

New England Charter Yachts

New England isn't as flashy as Florida or the South of France, but you can find any type of yacht you desire.

See our New England Crewed and Luxury Charter Yachts

See our New England Bareboat Charter Yachts

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