11 days in New York City, Boston & Portland Itinerary

11 days in New York City, Boston & Portland Itinerary

Created using Inspirock United States travel planner

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Route & dates

11 days in New York City, Boston & Portland Itinerary

Start: Nashville
Fly:  2​h 30​min
1
New York City
— 4 nights
AMTRAK from NYC TO BOSTON:  4​h
2
Boston
— 3 nights
Drive:  2​h
3
Portland
— 2 nights
Drive:  24​h 45​min
End: Manhattan

4
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.
You've now added The Loeb Boathouse to your itinerary. There's still lots to do: go for a walk through Central Park and don't miss a visit to Times Square.

To see ratings, maps, more things to do, and tourist information, read New York City trip planner .

Nashville to New York City is an approximately 5.5-hour combination of flight and bus. You can also fly; or drive. The time zone difference when traveling from Nashville to New York City is 1 hour. Traveling from Nashville in October, you will find days in New York City are slightly colder (70°F), and nights are about the same (57°F). You'll set off for Boston on the 13th (Sun).

Things to do in New York City

Neighborhoods Parks Outdoors
Highlights from your plan
Central Park ©
Central Park
Times Square ©
Times Square
The Loeb Boathouse ©
The Loeb Boathouse

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 discover tucked-away gems like North End and Old State House. Deepen your sense of the past at sights like Louisa May Alcott's Orchard House and Hancock-Clarke House. Venture out of the city with trips to Plymouth (Burial Hill & National Monument to the Forefathers) and Scituate Lighthouse (in Scituate). The adventure continues: explore the different monuments and memorials at Sleepy Hollow Cemetery, take a tour of Charlestown Navy Yard, ponder the world of politics at Massachusetts State House, and appreciate the extensive heritage of HarborWalk.

For photos, ratings, traveler tips, and more tourist information, go to the Boston online trip itinerary maker .

Traveling by combination of bus and flight from New York City to Boston takes 3 hours. Alternatively, you can fly; or drive. Traveling from New York City in October, expect Boston to be little chillier, temps between 64°F and 50°F. You'll have a few hours on the 16th (Wed) to wrap things up before traveling to Portland.

Things to do in Boston

Historic Sites Museums Neighborhoods

Side Trips

Plymouth, Concord, Hancock-Clarke House, Scituate Lighthouse
Highlights from your plan
North End ©
North End
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House
Old State House ©
Old State House

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.
Visit Marginal Way Walkway and Mount Agamenticus for their historical value. You'll discover tucked-away gems like Wadsworth-Longfellow House and Casco Bay. You'll find plenty of places to visit near Portland: Portsmouth Harbor Lighthouse (in New Castle) and Hamilton House (in South Berwick). Next up on the itinerary: enjoy the sea views from Portland Breakwater Lighthouse, indulge your thirst for a good beer at Shipyard Brewing Company, learn about winemaking at Maine Mead Works, and explore the different monuments and memorials at Eastern Cemetery.

To see more things to do, maps, other places to visit, and more tourist information, go to the Portland trip planner .

Getting from Boston to Portland by car takes about 2 hours. Other options: take a bus; or take a train. Plan for little chillier nights when traveling from Boston in October since evenings lows in Portland dip to 43°F. Cap off your sightseeing on the 18th (Fri) early enough to travel back home.

Things to do in Portland

Historic Sites Parks Nature

Side Trips

South Portland, Portsmouth Harbor Lighthouse, Hamilton House, Mount Agamenticus, Marginal Way Walkway
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portsmouth Harbor Lighthouse ©
Portsmouth Harbor Lighthouse
Mount Agamenticus ©
Mount Agamenticus

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