8 days in Portland, Boston & Salem Itinerary

8 days in Portland, Boston & Salem Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
Fly
1
Portland
— 2 nights
Train
2
Boston
— 3 nights
Train
3
Salem
— 2 nights
Drive to Logan International Airport, Fly to Washington

S M T W T F S
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Portland

— 2 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.
Start off your visit on the 9th (Sat): do a tasting at Maine Mead Works and then kick back and relax at Casco Bay. Here are some ideas for day two: admire the masterpieces at Ogunquit Museum of American Art, then get a taste of the local shopping with PANACHE FINE JEWELRY AND ART GALLERY, and then get to know the fascinating history of Marginal Way Walkway.

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Washington to Portland is an approximately 5-hour flight. You can also drive. Plan for little chillier temperatures traveling from Washington in October, with highs in Portland at 62°F and lows at 43°F. Wrap up your sightseeing on the 11th (Mon) to allow time to drive to Boston.

Things to do in Portland

Museums · Parks · Outdoors · Wineries

Side Trip

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Boston

— 3 nights

Beantown

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.
Louisa May Alcott's Orchard House and The Mapparium will appeal to museum buffs. Your cultural itinerary includes sights like Sleepy Hollow Cemetery and Longfellow House Washington's Headquarters National Historic Site. When in Boston, make a side trip to see The Old North Bridge in Concord, approximately Concord away. There's much more to do: take an in-depth tour of Old State House, get lost in a book at John F. Kennedy Presidential Museum & Library, contemplate the long history of Charlestown Navy Yard, and appreciate the extensive heritage of Freedom Trail.

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Getting from Portland to Boston by car takes about 2 hours. Other options: take a bus; or take a train. Plan for somewhat warmer nights when traveling from Portland in October since evenings lows in Boston dip to 50°F. Wrap up your sightseeing on the 14th (Thu) early enough to drive to Salem.

Things to do in Boston

Side Trips

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Salem

— 2 nights

Witch City

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Deepen your sense of the past at sights like The Custom House and Pickering Wharf. Eschew the tourist crowds and head to Salem Food Tours and Salem Maritime National Historic Site. There's still lots to do: take an in-depth tour of The House of the Seven Gables, examine the collection at Salem Witch Village, and admire the masterpieces at Peabody Essex Museum.

To see where to stay, maps, photos, and tourist information, read Salem trip planner.

Traveling by car from Boston to Salem takes an hour. Alternatively, you can take a train; or take a bus. Traveling from Boston in October, Salem is little chillier at night with lows of 45°F. Finish your sightseeing early on the 16th (Sat) to allow enough time to travel back home.

Things to do in Salem

Museums · Historic Sites · Wineries · Tours
Find places to stay Oct 14 — 16:
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