Portland itinerary scene

Weekend itinerary

Old Port mornings, Casco Bay ferry afternoons

Give the morning to Old Port's cobblestones and the Casco Bay ferry, then let dinner decide the evening — Portland's best tables sit within a short walk of the water.

By Cal Mercer — a Second Star Guide itinerary

Portland’s weekend connects Old Port brick, working piers, Casco Bay ferries, island shore roads, and a restaurant scene concentrated within a walkable peninsula.

Best length

2 nights

Two nights cover an Old Port arrival, one Casco Bay outing, a destination dinner, and an Eastern Promenade walk without sacrificing most of Sunday to the road.

Stay

Portland Harbor Hotel

In the historic Old Port, Portland Harbor Hotel offers coastal-styled rooms and suites, executive suites with double-sided fireplaces, and guest-floor pantries for coffee and…

Main activity

Old Port and a Casco Bay ferry to Peaks Island

Old Port supplies the brick streets and working piers; Peaks Island supplies the Casco Bay crossing, shore roads, and island views.

Weekend outline

Old Port and Casco Bay

Friday stays on the peninsula, Saturday crosses the bay or reaches the lighthouse shore, and Sunday returns to the Eastern Promenade before checkout.

Friday

Check in, walk Old Port, and eat near the working waterfront.

Start uphill on Exchange and Fore Streets, descend through Wharf Street to Commercial Street, and arrive at dinner after seeing the piers and ferry terminal.

4:00 PM

Saturday

Take Casco Bay Lines to Peaks Island, then return for dinner.

Board at the Maine State Pier, cross the harbor, and follow Peaks Island roads toward city views, beaches, and Battery Steele before the return ferry.

4:30 PM

Afternoon

Return through East Bayside or Congress Street.

After the ferry, choose East Bayside breweries, the Portland Museum of Art, or a short hotel break before the evening reservation.

Highlight
The trip’s main event
Viator

Historic Sightseeing Tour of Portland and Three Lighthouses

A guided Portland sightseeing outing focused on local history and three coastal lighthouses.

Check availability

Sunday

Walk the Eastern Promenade before coffee and checkout.

Fort Allen, the harbor overlooks, and the paved promenade give Sunday a different Portland view from Old Port’s brick streets and wharves.