37 days in New York City, North of Boston & Greater Merrimack Valley & Portland Itinerary

37 days in New York City, North of Boston & Greater Merrimack Valley & Portland Itinerary

Created using Inspirock United States trip planner

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

Route & dates

37 days in New York City, North of Boston & Greater Merrimack Valley & Portland Itinerary

Start: Sydney
Fly + bus:  26​h
1
New York City
— 13 nights
Drive:  4​h 45​min
2
Gloucester
— 9 nights
Drive:  2​h
3
Portland
— 12 nights
bus + Fly:  27​h
End: Sydney

13
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.
Go for a jaunt from New York City to Bronx to see Bronx Zoo about 36 minutes away. There's much more to do: take in the pleasant sights at Central Park, get great views at Top of the Rock, explore the world behind art at The Metropolitan Museum of Art, and take a stroll through Times Square.

For ratings, traveler tips, more things to do, and other tourist information, you can read our New York City attractions planner.

Sydney, Australia to New York City is an approximately 26-hour combination of flight and bus. You can also do a combination of train, flight, and bus. Due to the time zone difference, you'll gain 15 hours traveling from Sydney to New York City. Traveling from Sydney in September, things will get a bit warmer in New York City: highs are around 31°C and lows about 22°C. Finish your sightseeing early on the 21st (Mon) to allow enough time to drive to Gloucester.

Things to do in New York City

Museums Historic Sites Parks

Side Trips

Brooklyn Botanic Garden, Bronx Zoo, Cathedral Basilica of the Sacred Heart
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

9
nights
Gloucester

Gloucester ©
The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
Explore the numerous day-trip ideas around Gloucester: Independence Park (in Beverly), Salem (Salem Maritime National Historic Site, Pickering Wharf, & more) and Nashua River Rail Trail (in Ayer). The adventure continues: contemplate the long history of Louisa May Alcott's Orchard House, walk around Benson Park, take an in-depth tour of Concord Museum, and get up close to creatures of the deep with a dolphin and whale watching tour.

For photos, traveler tips, reviews, and tourist information, you can read our Gloucester trip tool .

You can drive from New York City to Gloucester in 5 hours. Alternatively, you can do a combination of bus and flight; or fly. Traveling from New York City in September, things will get little chillier in Gloucester: highs are around 28°C and lows about 14°C. Finish your sightseeing early on the 30th (Wed) so you can drive to Portland.

Things to do in Gloucester

Parks Historic Sites Outdoors

Side Trips

Salem, Concord, Rockport, York, Essex
Highlights from your plan
Walden Pond State Reservation ©
Walden Pond State Reservation
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House
Peabody Essex Museum ©
Peabody Essex Museum

12
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.
Get out of town with these interesting Portland side-trips: Rock Paper Scissors (in Wiscasset), St. Ann's Episcopal Church (in Kennebunkport) and Marginal Way Walkway (in Ogunquit). There's lots more to do: admire the natural beauty at Coastal Maine Botanical Gardens, visit a coastal fixture at Pemaquid Point Lighthouse, admire the sheer force of Glen Ellis Falls, and kick your exploration up a notch at some of the top local zipline courses and adventure parks.

Inspirock's itinerary builder makes planning a Portland trip simple and quick.

You can drive from Gloucester to Portland in 2 hours. Other options are to take a train; or take a bus. In September in Portland, expect temperatures between 26°C during the day and 13°C at night. On the 12th (Mon), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Portland

Parks Nature Historic Sites

Side Trips

Boothbay, Boothbay Harbor, Phippsburg, Lincoln, Pemaquid Point Lighthouse
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens
West Rattlesnake Mountain ©
West Rattlesnake Mountain

Similar Plans

38 days in United States BY A USER FROM AUSTRALIA April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular & hidden gems PREFERENCES: April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 17 days in New York City BY A USER FROM AUSTRALIA December, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular sights PREFERENCES: December, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Fast-paced 39 days in New York City & Los Angeles BY A USER FROM SAUDI ARABIA November, culture, outdoors, relaxing, historic sites, wildlife, popular sights PREFERENCES: November, culture, outdoors, relaxing, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 4 days in New York City BY A USER FROM UNITED STATES November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular & hidden gems PREFERENCES: November, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 11 days in New York City BY A USER FROM BRAZIL December, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: December, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 38 days in United States BY A USER FROM AUSTRALIA July, outdoors, historic sites, shopping, fast-paced, popular & hidden gems PREFERENCES: July, outdoors, historic sites, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 60 days in United States BY A USER FROM PHILIPPINES January, kids, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: January, kids, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 43 days in United States BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, beaches, historic sites, wildlife, slow & easy, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 11 days in New York City BY A USER FROM POLAND July, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, slow & easy, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 15 days in New York City & Boston BY A USER FROM FRANCE July, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: July, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 43 days in United States BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, beaches, historic sites, wildlife, slow & easy, popular sights PREFERENCES: July, culture, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy
View more plans