Private Sunset Charter on a Vintage Lobster Boat with Drinks

With over 200 islands that are home to both tiny coastal fishing towns and Maine's largest city, Casco Bay is vibrant, scenic, and a great way to experience Maine's incredible beauty, world-class cuisine, and wonderful boating opportunities.

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.

This is the smallest and first of four lighthouses we will encounter on our cruise through Casco Bay. On windy days, keep an eye out for gatherings of expert kite flyers and their colorful kites. Sometimes there's even a giant purple octopus floating lazily in the breeze!

Just around the corner from Bug Light is a statue of the bow of a Liberty Ship. Many ships were constructed here during WWII, including the S.S. Jeremiah O'Brien, which is a popular tourist attraction in San Francisco and one of the only surviving Liberty Ships.

See Portland Head Light, Maine's oldest and most iconic lighthouse, from the water. Commissioned by George Washington and constructed starting in 1791, this lighthouse has been an important navigational beacon and local landmark for more than 2 centuries.

The lighthouse has withstood hurricanes and global conflicts. German U-boats sunk a US Navy ship just 15 miles off the Head Light in the waning days of WWII.

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.

See some of the most incredibleEnjoy 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.