Portland · 3-day itinerary
3 Days in Portland, Maine: A Grown-Up Itinerary
Three days in Portland gives you one day in the Old Port, one on the water and the Cape Elizabeth lighthouses, and one on the coast, with a memorable dinner every night.
- Day 1
- The Old Port: food tour, Portland Museum of Art, Fore Street, Hunt + Alpine
- Day 2
- The Mailboat Run, Portland Head Light, the Lobster Shack, Twelve
- Day 3
- Ogunquit's Marginal Way, then Scales and Top of the East
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Day 1: The Old Port
Eat your way around the city, then a big dinner.
Late morning
Old Port Culinary Walking Tour
Meets at 10 Moulton St
Three hours of tastings and stories; book ahead.
A three-hour, small-group walk through the Old Port's food and drink scene with local history along the way, run year-round by Maine Day Ventures.
Afternoon
Portland Museum of Art
7 Congress Square
An hour or two in the galleries on Congress Square.
The city's art museum, in the Arts District on Congress Square. Open daily 10 a.m. to 6 p.m., until 8 p.m. on Fridays, when entry is free from 4 p.m.
Dinner
Fore Street
288 Fore St
Sit where you can watch the wood fire; reserve by phone.
Portland's landmark since 1996: a big old warehouse room around a wood-fired oven, grill and turnspit, with a menu that changes daily with what farmers and fishermen bring in. Open nightly from 4:30 p.m.; reservations by phone.
Late
Hunt + Alpine Club
75 Market St
A nightcap at one of the country's best cocktail bars.
A two-time James Beard semi-finalist cocktail bar, opened in 2013 and renovated in 2025, with food to match the drinks. Opens at 3 p.m. Tuesday to Friday and 2 p.m. at weekends; closed Mondays. A few reservations are released, the rest is walk-in.
Day 2: The bay and the lighthouses
Out on Casco Bay in the morning, Cape Elizabeth in the afternoon.
Morning
Casco Bay Lines Mailboat Run
Ferry terminal, 56 Commercial St
The 10 a.m. mailboat out among the islands.
Ride along on the working ferry that delivers mail and freight to five Casco Bay islands, including Great Diamond, Long and Chebeague. Two and a half to three and a half hours, year-round, departing 10 a.m., noon and 3:15 p.m.
Afternoon
Portland Head Light & Fort Williams Park
1000 Shore Rd, Cape Elizabeth (15 minutes)
Heads-up: The lighthouse museum closes for the season after Indigenous Peoples Day (October 12, 2026).
The lighthouse and a walk around Fort Williams Park.
The classic Maine lighthouse, on the rocks inside a free public park with old gun batteries, the Goddard Mansion ruin and a small cove beach. The park is open sunrise to sunset year-round; parking is by card meter.
Late lunch
The Lobster Shack at Two Lights
225 Two Lights Rd, Cape Elizabeth
Heads-up: Seasonal: the 2026 season ends October 25.
Lobster on the rocks (open until October 25, 2026).
A lobster shack on the rocks by the sea, a local landmark since the 1920s, with picnic tables facing the ocean and the Two Lights lighthouse. Open daily 11 a.m. to 8 p.m. in the fall.
Dinner
Twelve
115 Thames St, Portland Foreside
The special-occasion dinner of the trip.
Modern New England cooking from chef Colin Wyatt (formerly of Daniel and Eleven Madison Park) in a 150-year-old brick building rebuilt brick by brick on the waterfront. Dinner from 5 p.m.; closed Mondays.
Day 3: The coast road
A drive south for a cliff walk, back for a rooftop sunset.
Day
Ogunquit's Marginal Way
Ogunquit, about 40 miles south
Walk to Perkins Cove and have lunch by the harbour.
A paved 1.25-mile cliff-top path from Ogunquit to Perkins Cove, lined with more than 30 benches, tide pools and a small lighthouse, ending at a harbour with a pedestrian drawbridge. Free, dawn to dusk, year-round.
Sunset
Top of the East
Westin Portland Harborview, 157 High St, 15th floor
Fifteen floors up, looking out over the bay.
A 15th-floor lounge with views over the city to Casco Bay, cocktails and small plates. Opens at 4 p.m. daily, until midnight on Fridays and Saturdays; reservations on OpenTable.
Dinner
Scales
Maine Wharf, 68 Commercial St
Seafood on Maine Wharf.
A seafood restaurant out on Maine Wharf, with complimentary valet parking and a patio in good weather. Dinner nightly; bar seats can be reserved, and walk-in names are taken from 4 p.m.
Swaps
- Rather relax than drive? Swap day 3's coast trip for a treatment at the Inn by the Sea Spa.
- Beer lovers: add Allagash Brewing's tour on the afternoon of day 1.
- Want a show? See what's on at Portland Stage or the State Theatre.
Inn by the Sea Spa
40 Bowery Beach Rd, Cape Elizabeth
The spa at a seaside resort in Cape Elizabeth, with massages, facials, body wraps and packages. Non-guests can book with a card on file.
Allagash Brewing
50 Industrial Way (10 minutes' drive)
The Belgian-style brewery behind Allagash White, with a flagship tasting room, food from Bite Into Maine and a brewery tour named one of the 10 best in the US.
Portland Stage
25A Forest Ave
Maine's professional theatre company. The 2026-27 season opens with Tom Stoppard's Arcadia (September 30 to October 25), then Rooted in November and It's a Wonderful Life: A Live Radio Play in December.
Everything here was checked in September 2026. Many places on the Maine coast are seasonal and close or cut their hours from mid-October, so confirm before you go.
Questions people ask
Is 3 days in Portland, Maine enough?
Yes. It covers the Old Port, a boat trip on Casco Bay, the Cape Elizabeth lighthouses and a day on the coast, with three very good dinners.
Do you need a car in Portland, Maine?
Not in the Old Port, which is walkable. You'll want one, or a tour, for Cape Elizabeth, Allagash and Ogunquit.
When is the best time to visit Portland, Maine?
June to mid-October, when everything is open. September and early October are quieter and often the nicest weather.