Boston to Maine, United States

What is it that called to the first settlers to stay and eke out a living from the land, battling harsh winters and Native Americans who didn’t want to give up their land or their way of life? What is it that makes the people living in this region so fiercely independent? Is it the weather during the summer, with the bright sunny days that seem to last forever, or when the fog rolls in and wraps itself around you with its dark cottony silence, or even the days of cold, slashing rain, when you can finally curl up with a good book and not feel guilty about it? Is it the coastline that varies from beaches to craggy cliffs, from cozy harbors to off-shore islands, with lighthouses scattered to guide you along the way? What ever it is, once experienced, it will call to you to return again and again.We will explore from Boston to the mid-coast of Maine. Since the voyage begins in Boston, you might want to take the opportunity to visit nearby Marblehead and Salem. Marblehead, with its rocky beach and magnificent harbor, historic homes and narrow streets, is New England as you imagined it when you dreamed of taking a New England charter holiday.

Salem is also a quick hop away, and since you are in the area, you will want to include it on your “must see” list. Just realize that Boston has grown around it, and it is not the colony of the 1690s that you read about in your history books. The Salem Witch Museum is great fun for young and old alike, and the actors do a magnificent job in bringing the Witch Trials of 1692 to life with lessons relevant to contemporary issues of human rights and tolerance. Time permitting, the House of the Seven Gables that was featured in Nathaniel Hawthorne’s 1851 novel of the same name is nearby and the tour there is excellent also. If you didn’t read the book in your freshman high school English class, never fear, there is an audiovisual program to fill you in on the plot.

Back to your charter yacht, and it is now time to head north and explore New England as it was seen by the first European settlers – from the deck of a vessel! Leaving Boston behind, you will go through Boston Harbor Islands State Park. This is an archipelago consisting of 30 islands, most of which are undeveloped. Georges Island is the visitor and transportation hub of the park; if you are not on your own yacht the only way to experience the islands is via the ferry from Boston.

Cape Ann is home to artists, who come for the unique quality of the light, and to generations of fisherman who have used it as their home port as they fished the Banks. Most recently the movie “Perfect Storm” portrayed Gloucester and its fishing community. Gloucester and Rockport are the most well-known towns in the area, clinging to their rocky shores and filled with restaurants and shops. Gloucester was not only the first settlement on Cape Ann, it is also the oldest seaport in the nation, having been established in 1623. The statue of the Gloucester fisherman is a New England landmark, and the inscription at the bottom reads: “They that go down to the sea in ships”, a fitting tribute to the more than 10,000 Gloucester fishermen that have been lost in three centuries of fishing. Each June during the Saint Peter’s Fiesta there is a Blessing of the Fleet Ceremony.

Rockport, another fishing village and major artists’ colony, is also home to a weathered red lobster shack that has held such a fascination for so many artists that is has actually been name Motif No. 1! Shhh – don’t tell anyone, but it is actually a replica of the original shack which was destroyed in a storm several years ago – maybe the Perfect Storm? Rockport is great fun to poke about in, with a terrific selection of galleries, craft shops and restaurants to choose from.

Next stop: New Hampshire with its total of 18 miles of coastal shoreline. Wait! You didn’t even know that New Hampshire had a shoreline? Don’t worry, it probably only means that by the time you were old enough to play with the State Map Puzzle, which graces most every home, someone had already lost the tiny states of Rhode Island, Vermont and New Hampshire, and those states had long ago been sucked up in the vacuum cleaner, never to be seen again. So, for heaven’s sakes, get out the atlas and see that New Hampshire does indeed boast a shoreline! Robert Frost wrote: “Just specimens is all New Hampshire has, One each of everything as in a show case, Which naturally she doesn’t care to sell….” The sentiment pretty much personifies and typifies New Hampshire. Tiny though it is, it does have a splendid variety of scenery: seacoast, the highest mountain peaks in all of New England, fertile farmlands, dense woodlands, and even a host of small islands, the Isle of Shoals. These offshore jewels are actually split between New Hampshire (Star, Lunging, and White) and Maine (Appledore, Duck, Cedar, Malaga, and Smuttynose). Yes, you read that right, there is actually an island named Smuttynose. Where else but in New England would you find such a name?

Capt. John Smith was the first European to map the Isle of Shoals in 1614. Only, at that time, he named them “Smith Isles”, but the name didn’t stick. Eventually the name of the Isle of Shoals was adopted, speculation being that they were not named for shallow water shoals, but for the abundance of fish, as “shoals” and “schools” of fish mean the same thing. Of the Isles, Capt. Smith wrote: “of all the foure parts of the world that I have yet seene not inhabited, could I but means to transport a colonie, I would rather live here”. However, when Smith was granted only these same tiny islands in payment for all his years of service, he was less than thrilled and never returned. Today they remain largely uninhabited, the main attractions being the Shoals Marine Laboratory on Appledore and the Oceanic conference facility on Star Island.

Ever since a small group of English fishermen landed on Odiornes’ Point (now the town of Rye, just south of Portsmouth) in 1623, independence and self-reliance have been traits exhibited by the people living here. In fact, on January 5, 1776, New Hampshire drew up its own constitution and declared its independence from England six months before the Declaration of Independence of July 4, 1776. New Hampshire’s only seaport, Portsmouth was once the capital of the state and homeport to a dynasty of merchant seamen. The shipbuilding industry increased the importance of Portsmouth Harbor, and with the establishment of Portsmouth Naval Shipyard in 1800, additional fortification of the area, beyond the early forts built for the protection of the colonists were needed. This period saw an additional four forts being constructed, with the final coastal fortification during WW II, when batteries were added to Fort Foster and Fort Dearborn was constructed. What this means to you is that there are plenty of forts that are historic sites or parks and all are fun places to spend time exploring.

Henry David Thoreau termed Maine the last remaining wilderness east of the Mississippi in his journal of 1846-1857. Indeed, today, 90% of Maine remains virtually uninhabited. Even though the first known European explorer, John Cabot, first set foot in Maine in 1497, it did not become a state in its own right until 1820.

The sea chills quickly as you move northeast, so if you are planning to swim in Maine, York Beach is the place to do it! York Beach has a long stretch of white sand, surrounded by dunes and marshes. If you don’t want to swim, York Village has many historic buildings, a colonial-period cemetery, and the oldest jail in America, the Old Gaol. Nearby Ogunquit means “beautiful place by the sea”, which indeed it is with its three-mile beach of inviting white sand. From the center of town, the legendary Marginal Way, a mile long path winds along the ledges high above the Atlantic, providing superb views of the ocean and shoreline tidal pools.

Past the Kennebunks lies Portland, Maine’s largest city (population 65,000) and the states’ commercial and cultural center. First settled in 1631, Portland was burned to the ground three times: by raiding Indians in 1676, by invading British troops in 1775, and by accident in 1866. From its beginnings, the city was an important maritime center, with its natural deepwater harbor, and because it was 100 miles closer to Europe than any other port in the United States. Over fishing of the Atlantic fisheries and lobster beds has cut into Portland’s trade, so many of the docks have been converted to other uses, including artist’s studios and retail shops. One of the “must sees” in Portland is the Maine Historical Society, with its many exquisite old houses, including the 1785 boyhood home of Henry Wadsworth Longfellow. The new Portland Public Market with its colorful displays of local seafood, baked goods, cheeses, produce and specialty foods sold by the people who make, catch or grow them is a fun diversion.

Camden, with its sparkling harbor, is a Maine classic; it is every traveler’s fantasy with postcard perfect scenery in every direction. The harbor bustles with activity, filled with fishing boats and cruising boats alike. So beautiful and popular in fact, that you might find it too busy and opt for the less hectic nearby Rockport, perched helter-skelter on a patch of hills overlooking the harbor with a lighthouse at its northern tip. The mile-long breakwater protects the harbor, and though not as beautiful as Camden, it might appeal to the person in search for a quieter pace.

We have now come to the most northerly stop of our journey, Mt. Desert Island, home to Acadia National Park and Bar Harbor. Viewed in 1604 by a Frenchman, Samuel Champlain, he wrote “The mountain summits are all bare and rocky…I name it Isles des Monts Desert.” Not real poetic, but unlike Capt. Smiths’ naming of his isles, the name stuck…even the French pronunciation, de zert, as in “I’ll skip the salad, just give me the dessert”. Acadia National Park was established in 1916 and occupies most of Mount Desert Island, as well as part of Isle au Haut to the south and the Schoodic Peninsula to the north. Much of the land was donated by George Door and by John D. Rockefeller Jr, who also paid for construction of many of the park’s roads.

Bar Harbor is where you go to relax after hiking the trails of Acadia. Once rivaling Newport, RI, for its wealth and extravagance, a great fire in 1947 that burned out of control for nearly a month destroyed much of the island, including most of the mansions. The few mansions that survived have been transformed into inns. Plenty to do in Bar Harbor, whether you want to stroll the shore path, explore the Abbe Museum, which has one of the largest collections of Native American craftwork in the Northeast, poke around its many shops, or sample some of the culinary delights in the restaurants. Or you just might want to get an ice cream cone and sit on a park bench overlooking the surrounding islands and contemplate that nagging question: What is it about New England that feels so much like home, calling you to return back again and again?


Day 1: After a short ride from Logan Airport, you arrive aboard Audra Anne, docked in the heart of historic Charlestown Navy Yard, home to such attractions as the Bunker Hill Monument and the USS Constitution (Old Ironsides).

Day 2: After breakfast we head for Marblehead, famous as a sailing town and the starting point of the Marblehead to Halifax race. Ashore you will find 19th century dwellings and great shopping. Try the Landing Pub, well worth the time!

Day 3: We’re off to Cape Ann, home of the oldest fishing village in the country, Gloucester, famous for the Gortons fisherman and the filming of “The Perfect Storm”. We will dock in Rocky Neck at the Studio Restaurant, in the center of New England’s largest Art colonies.

Day 4: Leaving Gloucester, we pass Eastern Point Lighthouse on our way to Rockport. We will anchor at the beautiful front beach and transport you by tender into this fabulous port. A trip to Rockport would not be complete without a trip to Hannah Jumper Restaurant on Donovan’s Wharf.

Day 5: This morning we head for the Coast of Maine, with an intriguing stop at the Isle of Shoals, just off the coast of New Hampshire. After lunching at Foye’s on Cedar Island, home of the best lobster roll anywhere; we head Down-East into Maine, arriving in Portland. The restored downtown is home to lovely shops, pubs and restaurants.

Day 6: We head east from Casco Bay, moving from the beach coast to the rocky coast of Maine and onto Camden. Climb Mount Battie forn an incredible view of Penobscot Bay.

Day 7: Our adventure is drawing to a close as we cruise up Penobscot River, once a major logging area and used as a backdrop for the ending of “The Hunt for Red October”. We arrive at Bangor where we say good-bye, and as you head for the airport, you are already planning your next adventure onboard Audra Anne!

Boston Yacht Charters Itinerary is courtesy of Capt. Jon Christiansen, M/Y Audra Anne

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