5 days in Boston, Portland & New Haven Itinerary

5 days in Boston, Portland & New Haven Itinerary

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Route & dates

5 days in Boston, Portland & New Haven Itinerary

Start: Allentown
Drive:  5​h 30​min
1
Boston
— 1 night
Drive:  2​h
2
Portland
— 2 nights
Drive:  4​h 30​min
3
New Haven
— 1 night
Drive:  3​h 30​min
End: Allentown

1
night
Boston

Boston ©
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.
Your day-by-day itinerary now includes Adams National Historical Park as well as The Salem Witch Walk. On the 15th (Sat), gain a rich perspective with The Salem Witch Walk.

To find traveler tips, other places to visit, and more tourist information, refer to the Boston vacation trip planner.

Allentown to Boston is an approximately 5.5-hour car ride. You can also do a combination of bus and flight; or take a bus. Expect a daytime high around 83°F in July, and nighttime lows around 67°F. Wrap up your sightseeing on the 16th (Sun) to allow time to take a bus to Portland.

Things to do in Boston

Historic Sites Parks Nature

Side Trips

Adams National Historical Park, The Salem Witch Walk
Highlights from your plan
Adams National Historical Park ©
Adams National Historical Park
Freedom Trail ©
Freedom Trail
The Salem Witch Walk ©
The Salem Witch Walk

2
nights
Portland

Portland ©
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.
Your list of things to see and do now includes Sabbaday Falls, Old Orchard Beach, Casco Bay, and other attractions. Kick off your visit on the 16th (Sun): enjoy the sea views from Portland Breakwater Lighthouse. Get ready for a full day of sightseeing on the next day: examine the collection at Maine Narrow Gauge Railroad Co. & Museum, then tour the pleasant surroundings at Old Orchard Beach, and then explore the activities along Casco Bay.

To see other places to visit, ratings, photos, and more tourist information, go to the Portland trip itinerary maker.

You can take a bus from Boston to Portland in 2 hours. Other options are to drive; or take a train. Plan for slightly colder nights when traveling from Boston in July since evenings lows in Portland dip to 62°F. Wrap up your sightseeing on the 18th (Tue) to allow time to drive to New Haven.

Things to do in Portland

Parks Nature Outdoors

Side Trips

Sabbaday Falls, Portland Breakwater Lighthouse, Old Orchard Beach
Highlights from your plan
Sabbaday Falls ©
Sabbaday Falls
Portland Breakwater Lighthouse ©
Portland Breakwater Lighthouse

1
night
New Haven

New Haven ©
New Haven, in the U.S. You've now added PEZ Visitor Center to your itinerary. Kick off your visit on the 19th (Wed): get all the information you need at PEZ Visitor Center.

To see other places to visit, maps, where to stay, and other tourist information, use the New Haven itinerary maker.

Getting from Portland to New Haven by car takes about 4.5 hours. Other options: do a combination of bus and train; or do a combination of flight and train. Traveling from Portland in July, expect a bit warmer with lows of 68°F in New Haven. Wrap up your sightseeing by early afternoon on the 19th (Wed) to allow enough time to drive back home.
Highlights from your plan
PEZ Visitor Center ©
PEZ Visitor Center

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