The Mailboat Run : Casco Bay Islands



Casco Bay Lines, operates passenger, vehicle and freight service year-round. Casco Bay Lines ensures that passengers have safe, dependable and reliable transportation, and is considered the “lifeline” for the residents of the islands. Casco Bay Lines’ ferries transport nearly one million passengers, 30,000 vehicles and 5,300 tons of freight annually. Casco Bay Lines also delivers the U.S. mail and transports island students to and from Portland. A wide range of scenic cruises and charter trips for celebrations, meetings and sightseeing are available as well.”

Mailboat run map

This is our fourth visit to Portland, Maine and what I never realised before was that it’s possible to take a trip around the islands of Casco Bay. On day trips we’d visited the Art Museum and done some shopping. Portland still has lots of independent, quirky shops – 3 excellent bookshops just a stone’s throw from our hotel, a hat shop, map shop, wool shops and various craft and fashion/clothes shops, plus some excellent places to eat. During our last stay I visited The Longfellow House and The Portland Observatory. Yesterday following our morning’s outing to LLBean we headed for the Casco Bay Lines booking office and bought two tickets for the afternoon “Mailboat Run”

Casco Bay LInes

An integral part of our island communities, the Mailboat is a true working boat carrying passengers, mail and freight to the islands of Casco Bay—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 on the Mailboat cruise.”

There was some commentary on our outbound journey. Various lighthouses were pointed out.

2 lighthouses

To the middle right is Portland Head Light at Cape Elizabeth the oldest mainland lighthouse in the US

Pocohantas Light

Can you see the tiny Pocahantas Light on Great Diamond Island? The smallest registered lighthouse?

Pumpkin Island

Pumpkin Island : green today but a blaze of orange by October

Fort Gorges

Fort Gorges an octagonal fort built in 1858

Cow Island

Cow Island


The Windjammer

lobster boat

Retrieving Lobsters

US postal service

Loading at Cliff Island


And unloading at Cliff Island

Between Gt Diamond and Little

Hulks of ships purposely wrecked in order to save the sand bar between two islands

Cliff island

We were allowed ashore briefly at Cliff Island


Returning to Portland after our three hour cruise. Portland Observatory can be seen in the centre

A beautiful and interesting half day on the water.


6 comments on “The Mailboat Run : Casco Bay Islands

  1. ms6282 says:

    With this and your Baltic trip you’re turning into a right Island Hopper 🙂

  2. Fran says:

    Great way to see so many islands…and a lovely day to do it too!

  3. dianabirchall says:

    Seems to me that the area is more like the Vancouver islands, than, say, the Hebrides. But I’m envious of your trip – island-hopping is my favorite thing!

    • Well, Diana, I know neither Vancouver nor The Hebrides but these islands struck me as being rather special. Some belong to Portland City and others are private. They all look to have different characters. Some have lots of permanent residents plus summer visitors and at least one has a primary school -with just one or two pupils. Island-hopping is OK if the waters are sheltered and calm. As they were in Casco Bay.

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