60 days in Portland Itinerary

60 days in Portland Itinerary

Created using Inspirock Portland planner

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Portland
— 59 nights

59
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.
Venture out of the city with trips to Ipswich (Crane Beach, Ipswich Ale Brewery, & more), Ogunquit (Ogunquit Beach, Marginal Way Walkway, & more) and Gloucester (Beauport, the Sleeper-McCann House, Dolphin & Whale Watching, & more). There's lots more to do: indulge your thirst for a good beer at Allagash Brewery, cast your line with a fishing tour, wander the streets of North End, and appreciate the extensive heritage of Freedom Trail.

To see ratings, where to stay, photos, and more tourist information, you can read our Portland day trip tool .

In May, daytime highs in Portland are 64°F, while nighttime lows are 45°F. Wrap up your sightseeing on the 29th (Mon) to allow time to travel back home.

Things to do in Portland

Parks Outdoors Historic Sites

Side Trips

Boston, Salem, Portsmouth, Gloucester, North Conway
Highlights from your plan
Allagash Brewing Company ©
Allagash Brewing Company
Marginal Way Walkway ©
Marginal Way Walkway
Portland Museum of Art ©
Portland Museum of Art

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