8 days in Boston & Portland Itinerary

8 days in Boston & Portland Itinerary

Created using Inspirock United States trip planner
Make it your trip
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Boston
— 3 nights
Fly
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Portland
— 4 nights
Fly

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Boston — 3 nights

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Venture out of the city with trips to Dolphin & Whale Watching (in Gloucester) and Ogunquit (Marginal Way Walkway & Perkins Cove). Next up on the itinerary: admire the natural beauty at Boston Public Garden, stroll around Boston Common, stop by North End, and buy something for everyone on your list at Faneuil Hall Marketplace.

Before you visit Boston, use our trip planner to discover what you can do and see there.

Use the Route module to find suitable travel options from your home destination to Boston. September in Boston sees daily highs of 75°F and lows of 59°F at night. Wrap up your sightseeing on the 11th (Sun) to allow time to fly to Portland.
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Parks · Historic Sites · Museums · Wildlife
Side Trips
Find places to stay Sep 8 — 11:

Portland — 4 nights

A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Get out of town with these interesting Portland side-trips: Multnomah Falls (in Bridal Veil) and Cannon Beach (Haystack Rock & Cannon Beach). The adventure continues: admire the natural beauty at Portland Japanese Garden, stop by Powell's City of Books, snap pictures at Hawthorne Bridge, and don't miss a visit to Pittock Mansion.

To see traveler tips, maps, more things to do, and more tourist information, you can read our Portland trip maker.

Traveling by flight from Boston to Portland takes 8 hours. Alternatively, you can drive; or take a train. The time zone difference moving from Eastern Standard Time (EST) to Pacific Standard Time (PST) is minus 3 hours. In September in Portland, expect temperatures between 76°F during the day and 55°F at night. Wrap up your sightseeing by early afternoon on the 15th (Thu) to allow time for the flight back home.
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Parks · Nature · Beaches · Outdoors
Side Trips
Find places to stay Sep 11 — 15: