6 days in Portland & Boston Itinerary

6 days in Portland & Boston Itinerary

Created using Inspirock United States holiday planner

Make it your trip
Fly
1
Portland
— 1 night
Drive
2
Boston
— 4 nights
Fly

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Portland

— 1 night

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.
On the 11th (Sat), visit a coastal fixture at Portland Head Light, then learn the secrets of beer at a beer tour and tasting, and then sample the tasty concoctions at Allagash Brewing Company. Here are some ideas for day two: enjoy the sea views from Nubble Lighthouse, appreciate the extensive heritage of Marginal Way Walkway, and then take in the dramatic natural features at Perkins Cove.

For reviews, maps, and other tourist information, use the Portland road trip website.

Newark to Portland is an approximately 3.5-hour flight. You can also drive; or do a combination of train and bus. Prepare for a bit cooler weather when traveling from Newark in September: high temperatures in Portland hover around 73°F and lows are around 52°F. Finish your sightseeing early on the 12th (Sun) so you can drive to Boston.

Things to do in Portland

Historic Sites · Breweries & Distilleries · Tours · Nature

Side Trips

Boston

— 4 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.
You'll find plenty of places to visit near Boston: Sandwich (Hoxie House, Heritage Museums & Gardens, &more), Shining Sea Bikeway (in Falmouth) and Plymouth Rock (in Plymouth). There's lots more to do: get up close to creatures of the deep with a dolphin and whale watching tour, explore the world behind art at Isabella Stewart Gardner Museum, take an in-depth tour of John F. Kennedy Presidential Museum & Library, and stroll around Boston Public Garden.

To see reviews, more things to do, traveler tips, and other tourist information, go to the Boston day trip planning website.

You can drive from Portland to Boston in 2 hours. Other options are to take a bus; or take a train. Traveling from Portland in September, plan for somewhat warmer nights in Boston, with lows around 59°F. Wrap up your sightseeing on the 16th (Thu) early enough to fly back home.

Things to do in Boston

Museums · Parks · Historic Sites · Outdoors

Side Trips