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 The Salem Witch Walk as well as Adams National Historical Park. Kick off your visit on the 16th (Sun): gain insight with The Salem Witch Walk.

For traveler tips, more things to do, and tourist information, use the Boston travel itinerary creator.

Allentown to Boston is an approximately 5.5-hour combination of bus and flight. You can also drive; or do a combination of bus and train. In July, daily temperatures in Boston can reach 83°F, while at night they dip to 67°F. Wrap up your sightseeing on the 17th (Mon) to allow time to take a bus to Portland.

Things to do in Boston

Historic Sites Parks Nature

Side Trips

The Salem Witch Walk, Adams National Historical Park
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 Portland Breakwater Lighthouse, Old Orchard Beach, Casco Bay, and other attractions. Kick off your visit on the 17th (Mon): see the interesting displays at Maine Narrow Gauge Railroad Co. & Museum, enjoy the sand and surf at Old Orchard Beach, then explore the activities along Casco Bay, and finally enjoy the sea views from Portland Breakwater Lighthouse. On the 18th (Tue), you'll have a packed day of sightseeing: admire the sheer force of Sabbaday Falls.

To see where to stay, maps, ratings, and more tourist information, refer to the Portland sightseeing planner.

Getting from Boston to Portland by bus takes about 2 hours. Other options: drive; or take a train. Traveling from Boston in July, you can expect nighttime temperatures to be slightly colder in Portland, with lows of 62°F. Finish your sightseeing early on the 18th (Tue) so you can 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 20th (Thu): get a new perspective on nature at Yale Peabody Museum of Natural History, then get answers to all your questions at PEZ Visitor Center, then get engrossed in the history at Boothe Memorial Park and Museum, and finally tour the pleasant surroundings at Silver Sands State Park.

For ratings, more things to do, traveler tips, and more tourist information, refer to the New Haven itinerary maker.

You can drive from Portland to New Haven in 4.5 hours. Alternatively, you can do a combination of bus and train; or do a combination of flight and train. Traveling from Portland in July, expect somewhat warmer with lows of 68°F in New Haven. Wrap up your sightseeing on the 20th (Thu) early enough to drive back home.

Things to do in New Haven

Parks Nature Museums

Side Trips

Boothe Memorial Park and Museum, Silver Sands State Park, PEZ Visitor Center
Highlights from your plan
Yale Peabody Museum of Natural History ©
Silver Sands State Park ©
Silver Sands State Park
PEZ Visitor Center ©
PEZ Visitor Center

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