10 days in New York City, Boston & Portland Itinerary

10 days in New York City, Boston & Portland Itinerary

Created using Inspirock United States tour itinerary maker

Plan created by another user.Make it yours

Route & dates

1
New York City
— 5 nights
2
Boston
— 3 nights
3
Portland
— 1 night

5
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, and shopping. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, walk around The High Line, make a trip to Rockefeller Center, and pause for some photo ops at Statue of Liberty National Monument.

To see where to stay, more things to do, reviews, and other tourist information, refer to the New York City trip planner.

Chicago to New York City is an approximately 5-hour flight. You can also drive; or take a bus. Traveling from Chicago to New York City, you'll lose 1 hour due to the time zone difference. June in New York City sees daily highs of °F and lows of °F at night. Finish up your sightseeing early on the 4th (Sat) so you can travel to Boston.

Things to do in New York City

Museums Parks Historic Sites
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Empire State Building ©
Empire State Building

3
nights
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.
Get out of town with these interesting Boston side-trips: Plymouth Rock (in Plymouth), Louisa May Alcott's Orchard House (in Concord) and Marginal Way Walkway (in Ogunquit). There's still lots to do: examine the collection at Heritage Museums & Gardens, explore the activities along Cape Cod Canal, get curious at Sandwich Glass Museum, and explore the world behind art at Museum of Fine Arts.

To see more things to do, traveler tips, ratings, and other tourist information, you can read our Boston online route planner.

You can fly from New York City to Boston in 3.5 hours. Alternatively, you can drive; or take a train. Traveling from New York City in July, expect a bit cooler with lows of °F in Boston. Finish up your sightseeing early on the 7th (Tue) so you can go by car to Portland.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Sandwich, Plymouth Rock, Mount Auburn Cemetery, Cape Cod Canal, Louisa May Alcott's Orchard House
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Mount Auburn Cemetery ©
Mount Auburn Cemetery

1
night
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.
Start off your visit on the 8th (Wed): enjoy the sea views from Portland Head Light, get interesting insight from Tours, and then indulge your thirst for a good beer at Allagash Brewing Company.

For photos, traveler tips, ratings, and more tourist information, read Portland trip planner.

Drive from Boston to Portland in 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Boston in July, you can expect nighttime temperatures to be a bit cooler in Portland, with lows of °F. Finish your sightseeing early on the 8th (Wed) so you can travel back home.

Things to do in Portland

Outdoors Wildlife Tours

Side Trip

Portland Head Light
Highlights from your plan
Fishing Charters & Tours
Portland Head Light ©
Portland Head Light
Allagash Brewing Company ©
Allagash Brewing Company

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