8 days in Massachusetts & Portland Itinerary

8 days in Massachusetts & Portland Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
Drive
1
Sandwich
— 1 night
Drive
2
Boston
— 4 nights
Drive
3
Portland
— 2 nights
Drive

S M T W T F S
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Sandwich

— 1 night
Sandwich is a town in Barnstable County, Massachusetts, United States. On the 10th (Sat), appreciate the history behind Plymouth Rock, contemplate the long history of Mayflower II, make a trip to Old King's Hwy, then get engrossed in the history at Sandwich Glass Museum, and finally contemplate the waterfront views at Cape Cod Canal. On the 11th (Sun), you'll have a packed day of sightseeing: grab your bike and head to Shining Sea Bikeway, then admire the natural beauty at Spohr Gardens, then take an in-depth tour of Plimoth Patuxet, and finally admire the majestic nature at National Monument to the Forefathers.

To see where to stay, more things to do, maps, and more tourist information, read Sandwich road trip app.

Boston to Sandwich is an approximately 1.5-hour car ride. You can also take a bus. April in Sandwich sees daily highs of 54°F and lows of 36°F at night. Finish up your sightseeing early on the 11th (Sun) so you can go by car to Boston.

Things to do in Sandwich

Museums · Parks · Trails · Historic Sites

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.
Boston is known for historic sites, museums, and parks. Your plan includes some of its best attractions: explore the world behind art at Museum of Fine Arts, see the interesting displays at John F. Kennedy Presidential Museum & Library, take in nature's colorful creations at Isabella Stewart Gardner Museum, and buy something for everyone on your list at Faneuil Hall Marketplace.

To see more things to do, maps, and tourist information, read Boston trip itinerary builder tool.

Traveling by car from Sandwich to Boston takes 1.5 hours. Alternatively, you can take a bus. In April, daytime highs in Boston are 56°F, while nighttime lows are 40°F. Finish your sightseeing early on the 15th (Thu) so you can drive to Portland.

Things to do in Boston

Museums · Parks · Historic Sites · Childrens Museums

Side Trip

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.
On the 16th (Fri), visit a coastal fixture at Nubble Lighthouse, get to know the fascinating history of Marginal Way Walkway, and then explore the striking landscape at Perkins Cove. Get ready for a full day of sightseeing on the next day: get engrossed in the history at Victoria Mansion, then visit a coastal fixture at Portland Head Light, then make a trip to United States Custom House, and finally see the top attractions with The Maine Brew Bus.

To see other places to visit, where to stay, maps, and more tourist information, go to the Portland trip builder tool.

Traveling by car from Boston to Portland takes 2 hours. Alternatively, you can take a bus; or take a train. Plan for a bit cooler nights when traveling from Boston in April since evenings lows in Portland dip to 34°F. Wrap up your sightseeing on the 17th (Sat) to allow time to drive back home.

Things to do in Portland

Historic Sites · Tours · Wineries · Breweries & Distilleries

Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.