• Portland - Step aboard the M/V MONHEGAN, a beautifully restored wooden lobster boat, and settle in as you cruise through Portland’s Harbor, passing wharves that date back to just after the Revolutionary War. Once one of the busiest harbors in the early United States, Portland’s history is evident in the impressive stone fortresses that guard the harbor.
• Bug Light Park - This small lighthouse marks the entrance to Portland Harbor and is typically the first of four lighthouses seen on our sightseeing tours aboard our vintage wooden boats.
• Spring Point Ledge Lighthouse - Get a close view of Spring Point Light and nearby Fort Preble, a small gun emplacement that was part of Portland’s Harbor Defenses. Initially, the lighthouse was not connected to the mainland by the granite breakwater that exists today, and ships that navigated incorrectly would run aground on the shallow ledge.
• Portland Head Light - Experience Maine’s most iconic lighthouse from the water. Weather and sea conditions permitting, time is spent in front of the lighthouse for photos and discussions about its history. The lighthouse is not open for tours as it remains an active navigational beacon.
• Ram Island Ledge Light - Situated on the opposite side of the harbor channel from Portland Head Light, Ram Island Light stands on a rocky ledge and at high tide appears to float, unattached to land. Unlike the stately Portland Head Light, Ram Island Light is weathered and gray, almost inaccessible, with a derelict pier leading to a ladder that requires a 30-foot climb to reach the door.
• Casco Bay - Casco Bay is renowned for its rugged islands, protected waters, and stunning scenery. Cruise past some of the bay’s 200+ islands, featuring tree-covered rocky cliffs, small fishing communities, and charming harbors.
• Fort Gorges - As the most prominent stone fortress protecting Portland Harbor, Fort Gorges is a landmark visible from much of Casco Bay, built on a rocky outcropping near Peaks and Little Diamond Islands and the mainland. Although it could fire over a dozen cannons on attackers from any sea route, it was never used in active battle due to advancements in artillery during the Civil War. The fort served as a storage facility for the army during World War II, utilizing underwater mines, electromagnetic sensing cables, and other systems to protect Portland and Casco Bay from German attacks.

Remember, Portland was home to a large shipyard during WWII and was the starting point of a pipeline supplying oil to Montreal and eastern Canada, making the region strategically important even in modern conflicts.

• Peaks Island - Enjoy breathtaking 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 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 retains a small-town charm.

By the time fall colors are in full display, most seasonal residents have returned to their usual homes, leaving Peaks with just a few hundred year-round residents who rely on a ferry or water taxi to reach the mainland.

• Private Charter for up to 6 guests (cost is a flat rate)
• Licensed Captain
• Local Guide
• All Fees and Taxes
• On-board restrooms
• Cooler, glassware, plates, & utensils for guest use
• Alcoholic beverages
• Carbonated beverages
• Bottled water

• Parking in Portland’s Old Port
• Gratuity for your Guide

Exclusive Private Tour! Step aboard a classic Maine Lobster Boat for a personalized, 2-hour lighthouse viewing and sightseeing adventure. Escape the crowds as the journey navigates through the islands of Casco Bay, showcasing four iconic lighthouses, historic 19th-century forts, and the breathtaking Maine coastline.

Departing from Portland’s Old Port, these charters are ideal for families and small groups. Each tour is entirely private, accommodating up to 6 guests, and welcomes all ages!

Enjoy the first round of drinks on us – Savor a local Portland, Maine beer or a glass of wine while admiring the stunning views!

For a full refund, cancel at least 24 hours before the scheduled departure time.