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Mailboat Run Cruise

Price: $20.00
Tour operates on different days and times throughout the year. Please check calendar.
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Tour Details
Tour Details

Mailboat Run Cruise

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 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 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.

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

Shore Excursion Size
Standard Group
Shore Excursion Type
Cultural, Scenic, Water
Shore Excursion Duration
3 Hours
Activity Level
Shore Excursion Leaves From
A 5 minute walk from the pier (details will be provided when this excursion is booked).
Food/Beverage Provided
We recommend wearing comfortable clothing and sensible rubber soled shoes for walking on the boat. A light jacket or sweater is recommended as it can be windy and cool on the water. Sunglasses are also suggested.
Guests must be able to step on and off boat. To access the upper deck, steps are required.
5 Stars5Based On 32 Reviews Review This Tour
5 StarsIn the end everything went well December 04, 2019

Reviewer: Ellen
Our ship run late with the immigration and it was clear we wouldn’t make it on time for our trip.I called them and they said - no problem , we will schedule you for the next boat...They were very nice and helpful. We had a great time on the boat. The captain functioned as a tour guide too.

5 StarsGreat Day on the Water!November 27, 2019

Reviewer: sue schuman
This was the best way to spend a day on the coast at an EXTREMELY reasonable price. The dock is just a short walk from where the cruise ships dock. Would highly recommend it

5 StarsUnique ExperienceNovember 22, 2019

Reviewer: Margaret Kroitor
I enjoyed this excursion very much. It was a unique experience, combining a boat ride with local deliveries - not just mail. The run I was on delivered windows, a car, lumber, and much more to several islands in the area. I highly recommend this tour and I would do it again.

4 StarsMailboat runNovember 21, 2019

This was a very different type of excursion. Even though it was raining, we got to see the islands and the way people get around by boat in Casco Bay.

5 StarsGood valueNovember 09, 2019

Reviewer: Olga Woodall
Had a great time! It was lovely, and the boat Captain and crew knew their stuff!

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