Board M/V MONHEGAN, a beautifully restored wooden lobster boat, and make yourself at home as you cruise through Portland’s Harbor, past wharves dating to the period just after the Revolutionary War. At one point, Portland was one of the busiest harbors in the early decades of the United States, a fact attested to by the incredible stone fortresses protecting the harbor.

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Marking the entrance to Portland Harbor, this small lighthouse is typically the first of four lighthouses we see on our sightseeing excursions aboard our vintage wooden boats.

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Get up close to Spring Point Light and nearby Fort Preble, a small gun emplacement built as a part of Portland’s Harbor Defenses. In the early years, the lighthouse was not connected to the mainland by the granite breakwater that exists today, and ships that went on the wrong side of the lighthouse went aground on shallow ledge.

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See Maine’s most iconic lighthouse from the water. Weather and sea conditions permitting, we spend time in the waters in front of the lighthouse for photos and discussion about the history of the lighthouse. We do not go ashore or tour the lighthouse. Lighthouse is not open for tours as it is still an active navigational beacon.

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Marking the opposite side of the harbor channel from Portland Head Light, Ram Island Light sits atop a rocky ledge and at high tide appears to be floating and completely unattached to land. Whereas Portland Head Light has its stately keeper’s house and beautiful white washed sides, Ram Island Light is weathered and gray almost inaccessible, with a now-derelict pier leading to a ladder that requires one to climb up 30 feet on the outside of the lighthouse before you get to the door.

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Casco Bay is world-renown for its rugged islands, protected waters, and fantastic scenery. Cruise past some of the bay’s 200+ islands boasting tree-covered rocky cliffs, small fishing communities, and cute harbors.

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As the most conspicuous stone fortress protecting Portland Harbor, Fort Gorges is a landmark visible from much of Casco Bay, which is exactly why it was built on this rocky outcropping a short distance from Peaks and Little Diamond Islands and the mainland itself. The fort could fire more than a dozen cannons on attackers coming from any possible sea route, but was never used in active battle. Technological advancements in artillery during the Civil War rendered it too vulnerable to be useful. The fort did serve as a storage facility for the army during World War II, when underwater mines, electromagnetic sensing cables, and other systems were used to help protect Portland and Casco Bay from German attack.

Remember, Portland was home to a large shipyard during WWII and was the start of a pipeline that supplies oil to Montreal and eastern Canada, so the region was of high strategic importance even in more modern conflicts.

• Admission Ticket Included

Enjoy fantastic views of the scenic cliffs on Cushing Island and the tree-lined streets and quaint cottages of Peaks Island.

Once home to several amusement parks that were served by direct steamer routes from New York, Peaks is now a quiet island neighborhood that is technically part of the City of Portland but has a small-town feel all its own.

By the time the fall colors are in full view, most seasonal residents have returned to their usual homes, and Peaks is home to just a couple hundred hearty year round souls who must take a ferry or water taxi to get to the mainland.

• Admission Ticket Included