An integral part of the area’s island communities, the Mailboat is a true working boat carrying passengers, mail and freight to the islands of Little Diamond, Great Diamond, Long, Cliff and Chebeague. As the longest-operating service of its kind, this tour is a wonderful way to see the sights of the Bay.

Little Diamond Island was known as 'Little Hog Island' during colonial times. It is part of the city of Portland and as of the 2000 census, the island had a year-round population of 5. At low tide, Little Diamond Island connects to Great Diamond via a semi-submerged sandbar.

Great Diamond Island is another island in Casco Bay with a year-round population of 77. The island is not easily accessible by motor vehicle and has a limited network of roads. The primary modes of transportation are golf carts and bicycles.

Like other Casco Bay islands, Long Island was originally inhabited by Native Americans until settlers arrived in the 1600's. Colonel Ezekiel Cushing purchased the island in 1732 and is credited with being the first westerner to settle and build a house on Long Island. Soon after, other settlers arrived to make a livelihood out of farming, fishing, and catching lobsters. During WWII, Long Island served as a fueling depot for the U.S. Navy. Supply stations and army buildings were constructed on the island and many of these buildings still stand along the shore of the island.

Cliff Island is the smallest year-round island in Casco Bay. Shaped like an "H," the island has extensive property in conservation land, permanently protecting its rural atmosphere. The island is the only year-round island in Casco Bay that has all unpaved roads and, while cars are allowed, most people walk, bicycle or use golf carts for transportation.

Chebeague (pronounced: shuh-Beeg) is one of Maine’s most beautiful islands. At 3 ½ miles long and 1 ½ miles wide, Chebeague is the largest island in Casco Bay and is home to over 360 year-round people and over 4,000 summer residents. Its name means "isle of many springs." The island has a storied history of sailing, notably the stone sloopers, men who carried ballast for the sailing ships of the 19th century America and later granite for many of the country’s most spectacular buildings, including the Washington Monument. The many lovely Greek Revival homes on the island were built by these sloopers.

Please note: Restroom facilities are available on board for your convenience.