Yacht Charter Itinerary Boston, Massachusetts to Bar Harbor, Maine

Written by Missy Johnston

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Faneuil Hall

Start your yacht charter itinerary in Boston, and board your private charter yacht in Boston Harbor. After settling in, head into downtown Boston, just a hop skip and a jump away. Enjoy the evening by dining at any of Boston’s fine restaurants, and walk around historic Faneuil Hall, once a meeting hall and marketplace, and the surrounding historic market area, which is now filled with shops and restaurants. Wandering street musicians and magicians keep the area alive with activity. After, return back to your charter yacht for the night.

famous swan boats in boston

Boston, Public Garden Swan Boat

After enjoying breakfast, you may choose to visit such attractions in Boston as the Bunker Hill Monument and the USS Constitution, which was launched in Boston in 1797 and is the oldest commissioned warship afloat in the world. She was nicknamed “Old Ironsides” during the War of 1812 because of the way the British cannonballs were bouncing off her hull. There is a vast amount of history in Boston, and one way to see it all is to walk the Freedom Trail from the North End to the Boston Commons. Perhaps enjoy a ride on one of the Swan Boats in the Public Garden. Return to the yacht to leave Boston, and enjoy lunch on board while cruising out of Boston Harbor.

Dramatically lit house on the coast in historic marblehead massa

Marblehead Harbor

Cruise in the afternoon to 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. This is a lovely town in which to wander, sneaking peaks at the tiny hidden gardens behind the quaint colonial homes. The narrow little colonial roads meander around with a different little colonial home and garden around every turn. Overnight anchored in Marblehead Harbor.

salem massachusetts yacht charter

Salem Historic Area
Photo Credit Missy Johnston

After breakfast, it is a short cruise to nearby historic Salem, home to the Salem Witch Trials in the 1600’s. Visit the 1692 Salem Witch Museum for the full story of this historic event. After cruise to Cape Ann, home of the oldest fishing village in the country, Gloucester, which is famous for the Gortons’ fisherman statue and the filming and location of “The Perfect Storm”. Dock or anchor in the Rocky Neck area in the center of one of New England’s largest art colonies. And while cruising into or out of the main harbor; be sure to look for Gloucester’s most famous landmark, the statue of a fisherman that stands overlooking Gloucester Harbor. It is dedicated to the over 10,000 Gloucester fishermen lost at sea since the early 1600’s. Overnight anchored in Rocky Neck.

Rockport Maine yacht charter

Rockport Lobster Shack

Cruise in the morning out of Gloucester, passing Eastern Point Lighthouse before heading to Rockport. Anchor at the beautiful front beach and let your crew transport you via tender into this fabulous port. A walking street in this town is full of craft and artists shops. Enjoy walking and exploring the various shops in this festive area. Rockport is also home to the often photographed lobster shack covered with colorful lobster buoys. If lobster is of interest, this is a great location for a Maine lobster dinner ashore. Overnight in Rockport.

Wentworth Gardner House Portsmouth NH

Wentworth Gardner House Portsmouth NH

In the am head to Portsmouth, New Hampshire close to the mouth of the Piscataqua River, which divides New Hampshire from Maine. Claiming to be the third oldest city in the United States, Portsmouth was settled in 1623. In 2009, “Forbes Traveler” named Portsmouth as one of America’s prettiest towns. With a great mixture of historic architecture, life centers in Portsmouth around Market Square with sidewalk cafes, with great shops, little boutiques, artist’s galleries, and restaurants. Various historic houses are open for tours, and also a submarine, the USS Albacore. And don’t leave town without visiting the Strawberry Banke Museum on Puddle Dock, a living museum of buildings from four centuries, restored and revived and offering a great look at New Hampshire history.

Portland Ferry Maine

Portland Ferry

In the morning, head to Portland, Maine and dock right downtown in the Old Port. The Old Port is one of the most successful revitalized warehouse districts in the country. Seamlessly connected to the waterfront, the Old Port is a working waterfront and a chic shopping, dining, and entertainment district. Just steps from the water, one can stroll through the cobblestone streets and experience the quaint charm of this district. Restaurants serving Maine’s famous lobster dishes or the latest nouveau cuisine combine with a vibrant nightlife that is unparallel to any other New England city. The smell of the sea air, the sound of a foghorn, and the chatter of seagulls add to an atmosphere that is undeniably Portland, and undeniably Maine.

Maine Island coastline

Maine Island Coastline
Photo Credit Missy Johnston

After breakfast cruise over to deserted Jewell Island, your anchorage for lunch. At the southern end of the island, there is a multi-storied World War II observation tower (the taller of the two). Climb the internal stairs for dazzling, panoramic views of virtually the entire bay. Within are a dark labyrinth of underground passageways, and blind alleys which both fascinate and perplex. After lunch, cruise to the scenic harbor of Boothbay, a summer resort with natural beauty. Look out for whales in the outer harbor waters. Visit Ram Island Lighthouse and Burnt Island Light – a restored island and living history museum.

Fairy House in National Park Woods on Monhegan Island

Fairy House in National Park Woods on Monhegan Island

After breakfast, cruise to Monhegan Island where you will find excellent hiking ashore. Keep your eyes open for the little fairy houses that appear mysteriously that have been a part of the National Park for decades After lunch, a short cruise will have you in Rockland Harbor. The Rockland Harbor Trail is a public footpath of more than four miles along the historic waterfront of Rockland Harbor. The purpose of this trail is to showcase and help preserve unique aspects of Rockland’s waterfront, including historical, cultural, archeological, marine and natural history sites, as well as to provide public access for recreational enjoyment. In the morning before leaving, visit any of these Museums while at Rockland: Owls Head Transportation Museum, the Maine Lighthouse Museum, and the Penobscot Marine Museum.

Camden Maine yacht charter

Camden Maine
Photo Credit Missy Johnston

After a visit to Rockland museums in the am, take a short cruise up to Camden. There are many shops and restaurants near the waterfront and stores for provisions. Explore Camden and all of the little shops in the area for typically Maine souvenirs. Both Camden and Rockport are home to some of the Maine Windjammer fleet as well, many of which are National Historical Landmarks which you may see at some point sailing in or out of one of the harbors with all sails hoisted. Camden Harbor is a busy sailing and fishing harbor. Take time and watch the activity on the waterfront of this little Maine village.

Lobster Traps And Buoys

Maine Lobster Pots

Cruise to Vinalhaven, southernmost of the larger islands in Penobscot Bay. With its rugged shoreline, satellite islands, and scores of coves and anchorages, the eastern shore is full of gunkholes (deep indentations which may dry out at low tide) to explore. After having lunch, make your way over to Winter Harbor, one of the most rustic and unspoiled anchorages in Vinalhaven. Be sure to visit Seal Bay, equal to Winter Harbor for its unspoiled scenic beauty. This area is full of the summer homes of the rich and famous looking to be tucked away from it all.

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Acadia National Park

It is a short early morning cruise to Northeast Harbor. On the main street you will find attractive galleries and boutiques. Stretch your legs exploring this little Maine village maybe stopping for a lobster roll for lunch. Take a look at Southwest Harbor as well, home of Hinckley sailing yachts. After lunch cruise to Bar Harbor. Surrounded by Acadia National Park, Bar Harbor sits on the eastern shore of Mt. Desert Island and is the quinsentential Maine village. Acadia National Park has been voted one of the top 10 outdoor and adventure destinations in the United States by “Traveler’s Choice” awards. With miles of trails for biking or hiking, and beautiful views, pristine lakes, Acadian National Park has something for every outdoor enthusiast. Bar Harbor is full of history and great museums. Visit the Abbe Museum celebrating the Maine Native American. The Bar Harbor Historical Society features Bar Harbor in the “Gilded Age”. There is also the Bar Harbor Whale Museum and the Mt. Desert Oceanarium and lobster hatchery. And of course, there are plenty of shops and for a refreshing break stop to sample the brew at a micro brewery.

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Main Street Bar Harbor

Disembark to head for your next adventure.