Portland, Maine
A fishing port of 68,000 people on a peninsula in Casco Bay, rebuilt in red brick after the fire of 1866, whose wharves still land lobsters and fish right below the restaurants. Twenty minutes away lie Maine's oldest lighthouse, islands served by ferry and a rocky coastline dotted with beaches and fishing villages.
By PierrickLocal Guide ★8 · 14M+ views on Google MapsBy PierrickLocal Guide ★8 · 14M+ Maps views
🇺🇸 ⚓
Portland, Maine · Photo Alex O'Neal / Pexels
Things to do in Portland, Maine in 5 days
Day 1
Learn moreMore
Maine's oldest public art museum, founded in 1882, with a building by I. M. Pei's firm and a major collection of Winslow Homer, alongside Andrew Wyeth and the painters of the Maine coast.
💡 Entry is free on Fridays from 4 pm to 8 pm and all day on the third Thursday of the month. Visitors aged 21 and under get in free. Price: $20, about €17, adults.
Learn moreMore
The harbour district rebuilt in brick and granite after the great fire of 1866, with cobbled streets, Victorian warehouses full of shops and restaurants, and working wharves where lobster boats unload.
💡 Walk along the wharves early in the morning to see the fishing boats, then come back in the evening, when the restaurants liven up. Park in the municipal car parks, which are simpler than the cobbled streets. Price: free.
Day 2
Learn moreMore
A 26-metre wooden signal tower built in 1807 on Munjoy Hill to spot approaching ships, the last of its kind in the United States, with views over the whole bay from the top.
💡 Tours, in small groups, run without reservation on a first-come, first-served basis from late May to mid-October. The steps are steep, so good shoes are advisable. Price: about $10, or €9, adults.
Learn moreMore
A 28-hectare park on the slopes of Munjoy Hill whose lawns run down to Casco Bay, with a waterside trail to East End Beach and the best view of the islands from Fort Allen Park.
💡 Come at sunset with a picnic bought at a Munjoy Hill corner shop. The trail continues on foot or by bike to Back Cove, for a 6 km loop around the inner bay. Price: free.
Day 3
Learn moreMore
The inhabited island closest to Portland, 20 minutes by ferry, with a village of clapboard houses, a 6 km coast road and old Second World War batteries hidden in the woods.
💡 Take your bike on the ferry or hire one on the island: the loop takes an hour by bike, two to three hours on foot. Price: adult return $16, about €14, in high season, $8, about €7, in low season; bike $7, about €6.
Learn moreMore
Maine's oldest lighthouse, first lit in 1791, a 24-metre white tower on the rocks of Cape Elizabeth inside Fort Williams Park, with a small museum in the keeper's house.
💡 Come at sunrise, when the light comes off the sea and the car park is empty. The park is free, parking is paid by card, and the overflow car park is free. Price: parking $6, about €5, for two hours; museum $2, about €2, from late May to mid-October.
Day 4
Learn moreMore
A small town 30 km north of Portland built around the L.L.Bean flagship store, founded in 1912, with its giant boot, trout pond and outdoor school, plus dozens of outlet shops.
💡 Add Wolfe's Neck Woods State Park, 6 km away, for a forest walk beside the bay. Taster courses at the L.L.Bean outdoor school can be booked online. Price: free.
Day 5
Learn moreMore
A former shipbuilding port turned summer resort, with sea captains' houses, galleries and Dock Square, and Ocean Avenue running along the rocky coast to the Bush family's Walker's Point.
💡 Park outside Dock Square, which is saturated in summer, and walk. Combine it with Ogunquit and the Marginal Way coastal path, 20 minutes further south. Price: free.
"Book" (hotels) and "via GetYourGuide" (activities) are affiliate links (Booking, GetYourGuide). Prices, times and distances are approximate.
Take this plan everywhere
Download your itinerary (Portland, Maine) as a PDF: day by day, activities, times and where to stay. Matches the length you chose.
Don't feel like organising everything? A local partner travel agent can set it all up for you (flights, hotels, activities). We pass on your preferences and they call you back. Free and with no obligation.
Good to know before you go
🍽️ Must-try food
Burgers and barbecue
brisket and ribs cooked low and slow, done differently in every state.
Clam chowder in a sourdough bread bowl
the classic lunch on the San Francisco waterfront.
Mexican food
tacos from a truck in Los Angeles, a Mission burrito in San Francisco.
Pancakes and weekend brunch
a national habit, generous to the point of excess.
Craft beer, and California wine from Napa and Sonoma.
Dishes to look for in the good places: Portland, Maine.
⚠️ Best avoided
- Tipping is not optional: add 15 to 20% in restaurants and bars.
- Prices on menus and in shops exclude sales tax, which is added at the till.
- Do not plan more than four or five hours of driving a day: the distances are larger than they look on the map.
- Never travel without health insurance. A night in hospital can cost thousands of dollars.
- In summer, do not hike down into the Grand Canyon in the heat of the day: the climb back out is where people get into trouble.
Have you thought of…?
The little details that make all the difference once you're there.
Similar itineraries
📄 See the full guide: Portland, Maine, detailed month-by-month weather, budget, what to avoid and FAQ.