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

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.

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.

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.