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

This plan was created by another user.  Make it your plan

Route & dates

10 days in New York City, Boston & Portland Itinerary

Start: Chicago
Fly + bus:  4​h 45​min
1
New York City
— 5 nights
bus + Fly:  3​h
2
Boston
— 3 nights
Drive:  2​h
3
Portland
— 1 night
Fly:  5​h 15​min
End: Chicago

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, shopping, historic sites, and parks. Your plan includes some of its best attractions: make a trip to Central Park, pause for some photo ops at 9/11 Memorial, wander the streets of Times Square, and explore the world behind art at The Metropolitan Museum of Art.

To find other places to visit, ratings, photos, and more tourist information, refer to the New York City travel itinerary planner .

Chicago to New York City is an approximately 5-hour combination of flight and bus. You can also fly; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. In June, daytime highs in New York City are 80°F, while nighttime lows are 65°F. Finish your sightseeing early on the 4th (Sat) so you can travel to Boston.

Things to do in New York City

Museums Parks Historic Sites
Find places to stay Jun 29 — Jul 4:
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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.
You'll find plenty of places to visit near Boston: Sandwich (Heritage Museums & Gardens & Sandwich Glass Museum), Plymouth Rock (in Plymouth) and Marginal Way Walkway (in Ogunquit). And it doesn't end there: admire the masterpieces at Museum of Fine Arts, see the interesting displays at John F. Kennedy Presidential Museum & Library, stroll the grounds of Mount Auburn Cemetery, and steep yourself in history at Louisa May Alcott's Orchard House.

To find traveler tips, where to stay, and other tourist information, use the Boston day trip planner .

Getting from New York City to Boston by combination of bus and flight takes about 3 hours. Other options: fly; or drive. Expect slightly colder evenings in Boston when traveling from New York City in July, with lows around 67°F. Cap off your sightseeing on the 7th (Tue) early enough to go by car to Portland.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Sandwich, Mount Auburn Cemetery, Marginal Way Walkway, Plymouth Rock, Louisa May Alcott's Orchard House
Find places to stay Jul 4 — 7:
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Museum of Fine Arts ©
Museum of Fine Arts

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.
Kick off your visit on the 8th (Wed): see the interesting displays at Portland Head Light, then cast your line with a fishing tour, and then sample the tasty concoctions at Allagash Brewing Company.

To find where to stay, ratings, reviews, and more tourist information, you can read our Portland trip planner.

Getting from Boston to Portland by car takes about 2 hours. Other options: take a bus; or take a train. Traveling from Boston in July, expect a bit cooler with lows of 61°F in Portland. Finish up your sightseeing early on the 8th (Wed) so you can travel back home.

Things to do in Portland

Outdoors Tours Wildlife

Side Trip

Portland Head Light
Find places to stay Jul 7 — 8:
Highlights from your plan
Fishing Charters & Tours
Portland Head Light ©
Portland Head Light
Allagash Brewing Company ©
Allagash Brewing Company

Similar Plans

14 days in Boston BY A USER FROM UNITED STATES January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 12 days in United States BY A USER FROM UNITED STATES August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in New York City BY A USER FROM SPAIN March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: March, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 11 days in New York City BY A USER FROM ARGENTINA May, kids, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, slow & easy, popular sights PREFERENCES: May, kids, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Slow & easy 11 days in Boston BY A USER FROM CANADA May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 11 days in New York City BY A USER FROM ISRAEL February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 13 days in New York City BY A USER FROM EGYPT January, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: January, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 25 days in United States BY A USER FROM UNITED STATES January, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: January, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 11 days in New York City BY A USER FROM URUGUAY April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, popular sights PREFERENCES: April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 12 days in New York City BY A USER FROM MALAYSIA February, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: February, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 14 days in New York City BY A USER FROM UNITED ARAB EMIRATES March, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: March, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in New York City BY A USER FROM UNITED ARAB EMIRATES March, teens, kids, culture, outdoors, relaxing, historic sites, museums, shopping, popular sights PREFERENCES: March, teens, kids, culture, outdoors, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium
View more plans