5 days in Portland Itinerary

5 days in Portland Itinerary

Created using Inspirock Portland vacation planner

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1
Portland
— 4 nights

4
nights
Portland

Portland ©
Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Appreciate the collections at Portland Museum of Art and Portland Observatory. Take a break from the city and head to Fishing Charters & Tours and Casco Bay. The adventure continues: sample the tasty concoctions at Allagash Brewery, head off the coast to Casco Bay Islands, go for a stroll along the water at DiMillo's Old Port Marina, and don't miss a visit to Commercial Street.

To find other places to visit, ratings, maps, and other tourist information, you can read our Portland trip builder app .

October in Portland sees daily highs of 62°F and lows of 43°F at night. Wrap up your sightseeing on the 6th (Sun) early enough to travel back home.

Things to do in Portland

Outdoors Parks Trails
Highlights from your plan
Allagash Brewing Company ©
Allagash Brewing Company
Portland Museum of Art ©
Portland Museum of Art
Fishing Charters & Tours

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