Written by Missy Johnston

Portland Maine Headlands


Somewhat of an oxymoron, cruising north from Portland Maine to Camden Maine on a private yacht, enjoying a luxury yacht charter is actually cruising Down East in Maine. However no matter in which actual compass direction you are cruising, the coastline is lovely, including islands and little fishing villages, and the waters are full of New England fish and lobsters, while the shores are full of clams waiting to be raked or dug. For a special treat, enjoy a fresh lobster bake in clean seawater and seaweed right on the beach for real taste of Maine, followed by wild blueberry pie on a crewed yachtcharter along the coast of Maine.


Portland Maine Historic Downtown Building

Historic Portland

Join your yacht in Portland, Maine. The Old Port is one of the most successfully 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 the cobblestone streets and experience the quaint charm of this district. Maine’s famous lobster can be found in a variety dishes or sample the latest nouveau cuisine. Old Port is all about great food and boutique shopping combined with a vibrant nightlife. 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. Unpack and enjoy a relaxing cocktail as your yacht heads off to Falmouth Foreside, 5 miles northeast of Portland. Overnight.

After breakfast take a dinghy trip up the Royal River to Yarmouth, a quaint old fishing village. Later in the morning, head to South Freeport harbor on the Harraseeket River. There are a number of small islands, rock outcrops and ledges in upper Casco Bay. The Lobster Pound is a good place to pick out your lunch. Once you’ve finished lunch, head over to Potts Harbor, situated in a bight at the south end of Harpswell Neck. Overnight.

Portland ME

Casco Bay

Potts Harbor offers excellent views of Casco Bay’s archipelago. After lunch, a short cruise over to deserted Jewell Island is a great overnight stop. 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. A dark dripping labyrinth of underground passageways, conned chambers, and blind alleys both fascinate and perplex. Overnight.

Wake early to cruise up towards Kennebec River. From Seguin, the Kennebec River is about two miles to the north. Go 10 miles up the river to lunch at Bath. Famous for the Bath Iron works, America’s cup defender “Ranger” was built there. Visit the Maine Maritime Museum. After lunch head back down toward Sheepscot Bay and the Sheepscot River. Stay overnight at Five Islands Harbor. Ensure the chef picks out some fresh fish or seafood at the Georgetown Fisherman’s co-op for dinner. Stay overnight in Robinhood Cove.

Portland Maine harbor schooner heading to sea


Today you head over to the scenic harbor of Boothbay. A summer resort with natural beauty, there are many shore attractions. Look out for whales or puffins along outer harbor waters. Visit Ram Island Lighthouse and Burnt Island Light – a restored island and living history museum. Enjoy lunch before heading towards Damariscotta River to Overnight.

Look out for the oyster shell heaps of Damariscotta and Newcastle. They date back at least 2,400 years. Visit by land or water. These are ancient remnants of centuries of bivalve feasts left by Indians who summered along the shore of the Damariscotta River. Enjoy lunch ashore before heading towards Friendship, Cranberry or Harbor Islands to anchor overnight.

Monhegan Island Main HarborMonhegan Island

After breakfast, head over to Monhegan Island where there are excellent hiking trails ashore. Be on the lookout for fairy houses along the woodland trails. A short cruise will have you at 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. Visit any of these Museums while at Rockland: Owls Head Transportation Museum, the Maine Lighthouse Museum, and the Penobscot Marine Museum. You can go blueberry or raspberry picking, take a nature hike, or search for interesting seashells. Overnight.

Take only a short cruise up to Camden to disembark. There are many shops, boutiques and restaurants near the waterfront and stores for provisions. The Waterfront Restaurant is a popular place with a deck overlooking the harbor.