Written by Missy Johnston

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Enjoy the quaint islands of New England along with historic Newport, Rhode Island, and Old Mystic Seaport, a living museum of a busy seaport of yesteryear. This is an itinerary filled with local color, local character, and local colonial history while cruising through waters filled with fish, shellfish and the famous Maine Lobster. Visit Nantucket, Martha’s Vineyard, and Cuttyhunk Islands when cruising in southern New England on this private yacht charter itinerary.



Day 1: From 1851 to 1983, the USA retained yachting’s prestigious America’s Cup. The most famous races took place off Newport, where sailing is the No. 1 sport. The Museum of Yachting (Fort Adams State Park) tells the tale, while the International Yacht Restoration School (449 Thames Street) continues the tradition. Newport’s naval connection includes the Naval War College; whose museum focuses on naval strategy. Past the magnificent harbor and only a few steps from any of the city’s marinas, visitors will find fabulous mansions, colonial architecture and history, great music, trendy boutiques, and the International Tennis Hall of Fame. Newport is a living historical panorama from the earliest settlers in New England to the great mansions built by 19th century industrialists. There is drama on every step of the Cliff Walk and turn of Ocean Drive and spectacular beauty found in the beaches and harbor.

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After boarding, cruise to Sag Harbor, a large protected natural harbor, and as such was a perfect location for the colonial New England settlement, Sag Harbor Village, to burgeon on the surrounding shores. Today the Sag Harbor Village District is on the National Register of Historic Places surrounding a still well protected harbor, now mainly in use by visiting yachtsmen. Originally settled in the early 1700’s, Sag Harbor is said to have been named after a local tuber vine grown by the native Indians, the Metoac Algonquins, called the sagabon. By 1789, Sag Harbor had grown to be an important international port and a particularly important whaling ship port from whence whaling ships could head out to the greater Atlantic Ocean on the hunt for whales. The whaling industry hit a peak in the 1840’s in Sag Harbor, however not before making a big enough impact for the port to be mentioned several times in the famous whaling novel “Moby Dick”. While there, be sure to visit the Sag Harbor Whaling Museum, now housed in the original 1840’s Masonic Lodge, designed by Minard Lafever.
Today, Sag Harbor is a sleepy historic village which surrounds a large harbor, peopled by a generally upscale community as real estate in the area is at one of the highest values in the U.S. Relying in the summertime on tourism and local visitors that might be enjoying summering in “The Hamptons’, Sag Harbor has chic boutiques and specialty shops, and restaurants that feature local fresh seafood. Nearby are the many beaches that have made the area a destination for summertime fun. Overnight in Sag Harbor.

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Day 2: Leave early for Mystic Seaport, one of New England’s most popular attractions. In and around this meticulous recreation of a 19th-century seaport community, you can watch craftspeople at work, go aboard the Charles W. Morgan, the last remaining wooden whaling ship, and cruise on the river in a coal-fired steamboat and much, much more.

Mystic Seaport Village, a living museum, is comprised of over 30 New England trade shops and businesses, each in original historic buildings moved from various New England seaports. A bustling recreated seaport from the late 1800’s, each day Mystic Seaport comes alive with actor’s role playing as industrious New Englanders, dressed in period clothing, working trades and businesses that were all part of a prosperous New England port town. Visit the sail loft, where the sailmaker is repairing and making new sails for the Mystic Seaport vessels. Visit the ropewalk, where natural fibers are being twisted to form rope, which is a never-ending supply needed for sailing vessels.

Pop into the Ship Carver’s shop where fine figureheads are being carved to grace the bow of the various vessels. The “towns people” are well versed in their trades as done in the late 1800’s, and each has a story and tale to tell of their lives and loves in this historic seaport town.

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Day 3: Cruise from Mystic Beach to Nantucket. In the afternoon cruise around to Jetties Beach and anchor to enjoy the beach and water toys for fun in the sun. Twenty-six miles off the coast of Cape Cod, Massachusetts is the tiny island of Nantucket. Just 3.5 miles by 14 miles in size, this crescent-shaped New England island offers over 100 miles of pristine sandy beaches, all of which are accessible to the public.

Originally a booming whaling port, Nantucket Town has been named a National Historic District and has architecturally changed little since the 19th century, as seaside cottages, large Sea Captain homes, and old-fashioned lamps still line its streets. Whaling was a major industry in colonial New England including on this island and financially left an enormous stamp, as both Sea Captains and sailors flocked to Nantucket for the highly dangerous but financially lucrative, (for the lucky), hunt for whales. At the end of the 19th century an increase in size of the whaling ships marked the end of Nantucket as a whaling and financial center, as the larger ships could no longer access the harbor. The industry soon moved to the bigger harbor of nearby New Bedford. With the loss of the whaling business, Nantucket slumped into sleepy island life, locked in time, in the heyday of the 19th century. Return to the harbor late afternoon to anchor overnight.

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Day 4: Stay a second day to explore Nantucket. The Nantucket Whaling Museum is downtown and well worth visiting, with excellent displays including the everyday life of a whaling man. Take time to visit this museum and then wander the streets of Nantucket lined with the homes of the whaling wealthy from the 19th century. Look up along the roofs for the iconic widow’s walks, a high perch from which to search for the return of whaling ships into Nantucket Harbor. The town ringing the harbor is still laid out as it was when whaling ruled this island, with the same cobblestone streets and brick sidewalks, trod on by centuries of islanders.

Enjoy the wide sandy beaches, as beautiful as any in the world. Swim in the still, sparkling waters of Nantucket Sound to the north, or brave the mighty Atlantic along the island’s south shore. Let the pounding surf, and clean, salty air restore you. Take in the boutique shops, and explore the art galleries and museums. Celebrate Nantucket’s cultural offerings including theatrical performances, music, art, film, and literature. Sign up for a guided tour of the island or pick up a picnic lunch, and set off to discover Nantucket for yourself.

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Day 5: Cruise to Edgartown on Martha’s Vineyard, 22nm from Nantucket. This popular summer resort of Martha’s Vineyard was once a boomtown. Between 1820 and 1860 Edgartown thrived on the profits from New England whaling, and the grand Greek Revival and Federal mansions testify to the wealth garnered by whaling captains. Today, some are inns, others restaurants, while most are still private homes. Edgartown, is the most popular and well known town on the island. The Edgartown Yacht Club sits as a welcoming beacon at the opening of the harbor after the Chappaquiddick ferry landing. Named after the young son of King James II of England that died in 1671, Edgartown has been in existence since 1642 with historic buildings clustered along cobbled streets many featuring the famous New England architectural feature of the Widow’s Walk. The channel entrance by yacht into Edgartown opens into Katama Bay, which is a large bay with mooring balls and some anchorage for visitors. There is very little dockage, and most yachting visitors use a mooring ball, and either the ship’s tender for shore access or the harbor launch or water taxi service. The south end of Katama Bay has a barrier beach that sometimes connects the neighboring island of Chappaquiddick to Martha’s Vineyard. In 2007, a storm blew a hole in the barrier beach disconnecting Chappaquiddick Island from Martha’s Vineyard, and causing a 3 knot current to now run through the harbor. Head ashore to explore this village. Overnight.

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Day 6: Cruise to the tiny island of Cuttyhunk, perhaps stopping at one of the Elizabeth Islands to enjoy a virtually deserted beach for swimming and water sports.

Cuttyhunk is a quiet very peaceful island with a year around population of 80 that can swell to 400 in the summer. Cuttyhunk has been an important island in the history of New England. English explorers made landfall in Cuttyhunk in 1602, 6 years before Plymouth Plantation was founded on the mainland. In 1602, Bartholomew Gosnold, exploring the area with his men on board “The Concord”, built a fort on Cuttyhunk and stayed for a month, before returning to England. Cuttyhunk was in private ownership for several centuries, owned for two hundred years by the Slocum family. In 1858, the Slocum family sold the island and the town of Gosnold was established and prospered.

South of Cuttyhunk are the treacherous rocks of the Sow and Pigs Reef, which is a hazard to yachtsmen today; the most notable accident the 1992 grounding of the ocean liner “Queen Elizabeth”. The residents of Gosnold in the 1800’s developed a very lucrative business guiding whaling ships in from the Atlantic to New Bedford through these treacherous waters; guiding at the height of this business as many as 11 ships a day.

However, these same treacherous rocks are also an excellent striped bass fishing location. Many world record striped bass have been pulled from these waters, and today this area remains a top striped bass fishing spot. In the last half of the 19th century a very upscale fishing club was established on Cuttyhunk by powerful and wealthy men from New York City. From here on, the island was buzzing with activity into the early 20th century, with a firework display every Fourth of July.

Cuttyhunk is a mile and a half long and half a mile wide. At the eastern end of the island is an excellent natural harbor, which in the summertime offers haven for visiting yachts. There are also mooring balls available at the mouth of the harbor. Half of the island today is set apart as a nature preserve, and home to a wide variety of birds.

Shellfish farming takes place on the southern end of the island and striped bass fishing continues to be a large draw, however the real draw is the beauty, peace and quiet offered by this small little island. However check the local market for freshly caught sea bass, and you may see enterprising boys in little Boston Whalers touting their fresh shellfish for sale to visiting yachtsmen on yachts in the harbor.

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Day 7: Return to Newport, and pickup a mooring ball or dock in downtown Newport, for today is the day to explore Newport. Time spent enjoying the interactive audio and video exhibits in the Brick Market Museum of Newport History, touring The Redwood Library, America’s oldest library, or Touro Synagogue, America’s oldest synagogue, just a block or two from the Old Quaker Meeting House, and the White Horse Tavern, claimed to be the oldest continually run tavern in the United States is time well spent. Wander off the beaten path and stroll some of the quieter streets on Historic Hill and the Point and your eyes will be opened to a side of Newport that you never knew existed, a once busy colonial harbor town larger than either New York City or Boston, shut down, and locked in time by a British blockade during the Revolutionary War.

No other city in America has more restored colonial-era homes and buildings, almost 200, all protected by the National Register of Historic Landmarks. Within blocks of the historic colonial districts are the fabulous mansions of the 19th century wealthy, lined up along Bellevue Avenue. These paragons chose Newport as their place to “summer” in grandiose “cottages”, built as a statement of personal achievement and wealth. Enjoy guided tours of many colonial buildings and grand mansions and learn much about the lifestyles, tastes and diversions of those that called Newport home during the various centuries of city existence. Each guided tour is unforgettable highlighting the real-life of real people whose names are part of American legend: Commodore Perry, Vanderbilt and Astor, Doris Duke, and John F and Jackie Kennedy. There are also guided tours of the lives of those not so famous; showcasing the Downstairs existence of the Upstairs-Downstairs world of a 19th century upscale mansion. Ashore around the harbor are chic shops and boutiques and many restaurants and watering holes.

Enjoy nightlife as Newport is an active little village with shops open late. Take an evening stroll down docks such as Bannisters humming with activity until close to midnight.

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“The Breakers”

Day 8: In the morning after breakfast disembark your yacht and perhaps arrange for a limo to drive around Ocean Drive, stopping at “The Breakers” for a tour of the famous Vanderbilt Gilded Age Newport “Cottage” before heading to the airport, ending a great southern New England yacht charter, seeing all there is to see.