8 days in Portland & Monhegan Island Itinerary

8 days in Portland & Monhegan Island Itinerary

Created using Inspirock Maine tour itinerary planner

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Portland
— 5 nights
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Monhegan Island
— 2 nights
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Portland

— 5 nights

The Forest City

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.
Change things up with these side-trips from Portland: Salisbury Rail Trail (in Salisbury), Boston (Ghost & Vampire Tours, Faneuil Hall Marketplace, &more) and Dolphin & Whale Watching (in Gloucester). And it doesn't end there: get to know the fascinating history of Marginal Way Walkway, take in panoramic vistas at Portland Observatory, head off the coast to Casco Bay Islands, and explore the landscape on two wheels at Eastern Promenade Trail.

For where to stay, other places to visit, ratings, and other tourist information, read our Portland trip planner.

New York City to Portland is an approximately 3-hour flight. You can also drive; or take a bus. Prepare for a bit cooler weather when traveling from New York City in July: high temperatures in Portland hover around 79°F and lows are around 61°F. On the 16th (Fri), you'll travel to Monhegan Island.

Things to do in Portland

Tours · Parks · Outdoors · Breweries & Distilleries

Side Trips

Monhegan Island

— 2 nights
Keep things going the next day: step off the mainland to explore Monhegan Island, then examine the collection at Monhegan Museum, and then visit a coastal fixture at Monhegan Light.

To plan Monhegan Island vacation without wasting time, ask Inspirock to design an itinerary.

Explore your travel options from Portland to Monhegan Island with the Route module. When traveling from Portland in July, plan for slightly colder days in Monhegan Island, with highs around 74°F, while nights are about the same with lows around 58°F. Wrap up your sightseeing by early afternoon on the 18th (Sun) to allow time for travel back home.

Things to do in Monhegan Island

Museums · Parks · Historic Sites · Shopping