This 150-year-old Mailboat Is One of the Most Scenic Cruises in Maine—With Cute Cottages, Lobster Boats, and Whale Sightings
Portland’s 150-year-old Casco Bay Lines Mailboat Run wasn’t created for tourists, but welcomes them aboard anyway.
Credit: Taryn Shorr-Mckee/Travel + Leisure
Most sightseeing cruises center around scenery or spotting wildlife. Portland, Maine's historic mailboat offers plenty of both—but that's never been its primary purpose.
The Casco Bay Lines Mailboat Run has connected Portland with its island communities since the 1870s, making it the oldest continuously operating mailboat service in the United States. What began as (and remains) a practical way to deliver mail, packages, groceries, freight, and other supplies has become one of the state's most unexpectedly rewarding tours, offering a glimpse into everyday life in Casco Bay .
Rather than following a scripted route catering to tourists, the ferry sticks to its working schedule year-round. The result: a cruise that feels far more meaningful than a typical harbor tour, and one that also happens to showcase some of coastal Maine's most beautiful scenery.
A Working Ferry That Doubles As One of Portland's Best Cruises
| The passenger ferry dock on Cliff Island, located in Casco Bay, Maine. Credit: Taryn Shorr-Mckee/Travel + Leisure |
The ferry dock and marina at Diamond Cove on Great Diamond Island. Credit: Taryn Shorr-Mckee/Travel + Leisure |
Homes along Casco Bay. Credit: Taryn Shorr-Mckee/Travel + Leisure |
The Mailboat Run departs from the city's Old Port and winds through Casco Bay, stopping at Little Diamond, Great Diamond, Long, and Cliff islands. Depending on the passengers and deliveries that day, the route takes between 2.5 and 3.5 hours, with no two trips unfolding exactly the same.
Passengers look on as crewmembers unload everything from mail bags and grocery orders to furniture and building supplies, while island residents hop on and off at each dock. Most travelers never get to see these rhythms of island life , and the mailboat run gives them a front-row seat.
The June day I was on board, crews dropped off a washer and dryer, fresh produce for a restaurant, a case of wine, countless Amazon packages, and a large group attending a wedding. I found myself making up a game, imagining everyone's daily lives and assigning different potential storylines.
Along the route, the captain also narrates details about Casco Bay's history, the islands' year-round communities, and the landmarks outside the windows.
The scenery is equally memorable. The route cruises by Portland Head Light, Portland Breakwater Light (a.k.a. Bug Light), historic military forts, working lobster boats, and salt-stained cottages dotting the iconic rocky Maine shoreline. Wildlife sightings are common, with seals and bald eagles making regular appearances and whales popping up more occasionally.
One of the trip's most charming moments comes near the turnaround point at Cliff Island. When the schedule allows—typically when there are extra deliveries or a big freight load—passengers get a few minutes to step ashore. It's just enough time to stretch your legs, browse the island's general store, and pick up some ice cream or a snack before boarding for the return trip to Portland.
Unlike typical commercial cruises, the mailboat doesn't have an onboard cafe or bar—and that's part of the appeal. Passengers are encouraged to bring their own food and beverages, including alcohol, making the cruise feel like a leisurely picnic on the water. Before boarding, stop into one of the many shops in Old Port to assemble a spread of local meats and cheeses, crackers, fresh bread, or other goodies to enjoy during the voyage. Local favorites include Micucci Grocery , Casco Variety , and Standard Baking Co. for freshly baked bread and treats. The latter is owned by Dana Street, 2026 James Beard Award winner for Outstanding Restaurateur. (Street also owns the wildly popular Scales.)
Know Before You Go
Scenic view of Casco Bay. Credit: Taryn Shorr-Mckee/Travel + Leisure
The Mailboat Run operates year-round from the Casco Bay Lines terminal on Portland's waterfront, on the edge of the Old Port district. Three departures leave daily, with the last departure shifting slightly earlier in the summer.
Tickets cost $24 for adults, $14 for children, and $20 for seniors and passengers with disabilities. Because it's a working ferry first and a sightseeing cruise second, trip lengths vary depending on freight deliveries and operational needs.
The best seats are all outside, though they're covered, so bringing layers. Temperatures on the water feel noticeably cooler than they do in downtown Portland, even in summer. Remember to pack snacks and drinks, since there are no concessions on board aside from a single vending machine dispensing soda and water.
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