15 days in Boston & Portland Itinerary

15 days in Boston & Portland Itinerary

Created using Inspirock United States travel route builder

Plan created by another user. Make it yours
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Boston
— 7 nights
2
Portland
— 7 nights

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7
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Boston

Boston ©

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.
Escape the urban bustle at Boat Tours & Water Sports and Castle Island. Eschew the tourist crowds and head to Old State House and Count Orlok's Nightmare Gallery. You'll find plenty of places to visit near Boston: Plymouth (The Jenney & National Monument to the Forefathers), Concord (Louisa May Alcott's Orchard House, Sleepy Hollow Cemetery, &more) and Sandwich Glass Museum (in Sandwich). The adventure continues: steep yourself in history at Hancock-Clarke House, contemplate in the serene atmosphere at Old South Church, pause for some serene contemplation at Trinity Church, and visit North End.

To find reviews, maps, photos, and other tourist information, go to the Boston trip itinerary website.

Chicago to Boston is an approximately 4.5-hour flight. You can also fly; or drive; or take a bus. The time zone difference when traveling from Chicago to Boston is 1 hour. In October in Boston, expect temperatures between 64°F during the day and 50°F at night. You'll set off for Portland on the 16th (Fri).

Things to do in Boston

Side Trips

Highlights from your trip
©
Must see
Trinity Church
4.4

7
nights
Portland

Portland ©

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.
Discover out-of-the-way places like Eastern Promenade Trail and Maine Wildlife Park. Visit Marginal Way Walkway and Portland Head Light for their historical value. Venture out of the city with trips to Wells Reserve at Laudholm (in Wells), Bradbury Mountain State Park (in Freeport) and Ogunquit ( PANACHE FINE JEWELRY AND ART GALLERY & Footbridge Beach). The adventure continues: visit a coastal fixture at Spring Point Ledge Lighthouse, take a memorable drive along St. Anthony's Monastery, tour the pleasant surroundings at Mother's Beach, and admire the majestic nature at Two Lights State Park.

To see photos, maps, other places to visit, and more tourist information, you can read our Portland holiday maker tool.

You can drive from Boston to Portland in 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Boston in October, expect slightly colder with lows of 43°F in Portland. Cap off your sightseeing on the 23rd (Fri) early enough to travel back home.

Things to do in Portland

Parks · Historic Sites · Outdoors · Nature

Side Trips

Highlights from your trip
©
Must see
Footbridge Beach
4.8

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