Take this scenic Diamond Pass Run cruise tour of Maine’s Inner Casco Bay, past lovely Victorian cottages on the shorelines of Little and Great Diamond Island, and Peaks Island. Catch a glimpse of island life as we travel to four different stops.

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 five. Great Diamond Island, another island in Casco Bay, has 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. At low tide, Little Diamond Island connects to Great Diamond Island via a semi-submerged sandbar.

Like other Casco Bay islands, Long Island was originally inhabited by Native Americans until settlers arrived in the 1600s. 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. During World War II, 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. Once known as the Coney Island of Maine, and later an important WW II outpost, Peaks Island today is a neighborhood within the city of Portland. Home to artists, retirees, commuters of all sorts, and a substantial summer population, Peaks Island boasts a small-town feel with unparalleled ocean views and access.

An integral part of Portland, Maine’s island communities, the mailboat is a true working boat carrying passengers, mail and freight to the Casco Bay’s Little Diamond, Great Diamond, Long, Cliff, and Chebeague Islands. As the longest-operating service of its kind, this Maine Mailboat Run Cruise 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 five. Great Diamond Island has a year-round population of 77. The island is not easily accessible by motor vehicle and has a limited network of roads. At low tide, Little Diamond Island connects to Great Diamond Island via a semi-submerged sandbar.

Like other Casco Bay islands, Long Island was originally inhabited by Native Americans until settlers arrived in the 1600s. 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. During World War II, 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.

Cliff Island is the smallest year-round island in Casco Bay. Chebeague (pronounced: shuh-BEEG) is one of Maine’s most beautiful islands. At 3 miles long and 1 mile wide, Chebeague is the largest island in Casco Bay and is home to over 360 year-round people and over 4,000 summer residents The island has a storied history of sailing, notably the stone sloopers, men who carried ballast for the sailing ships of 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.

Enjoy this great opportunity for a Windjammer Sail onboard an authentic schooner in Maine’s beautiful Casco Bay. Sit back, relax and enjoy the views, or join the crew and learn about sailing.

Since the 1700’s, schooners have been used for a variety of purposes because they are fast, sleek, adaptable, and considered the sturdiest ships of all time. On this Windjammer Sail tour, you will board a beautiful 48-passenger vessel for a two-hour sail on Casco Bay.

This excursion provides the perfect way to experience the beauty of the Maine coast, complete with lighthouses, seals, seabirds and the rugged coastline. Pack a meal, bring your favorite wine or beer, and sit back and relax as our courteous and professional crew share their knowledge of the sea, sailing and local history. Or, if you feel inspired, join the crew to hoist the sails or take a turn at the ship’s wheel. All ages are welcome!