45 days in Massachusetts, New York City & Philadelphia Itinerary

45 days in Massachusetts, New York City & Philadelphia Itinerary

Created using Inspirock United States vacation planner

Make it your trip
Fly
1
Boston
— 9 nights
Fly
2
Provincetown
— 5 nights
Drive
3
Sandwich
— 3 nights
Taxi to 227 Clinton St., Falmouth, MA, Ferry to Oak Bluffs
4
Oak Bluffs, Martha's Vineyard
— 2 nights
Ferry
5
Nantucket
— 5 nights
Fly
6
New York City
— 10 nights
Train
7
Philadelphia
— 9 nights
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Boston

— 9 nights

Beantown

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.
Change things up with these side-trips from Boston: Salem (The House of the Seven Gables & Peabody Essex Museum), Stanley park (in Westfield) and Concord (Minuteman National Park - Old North Bridge, Louisa May Alcott's Orchard House, &more). And it doesn't end there: admire the masterpieces at Museum of Fine Arts, learn more about the world around you at The Harvard Museum of Natural History, engage your brain at Museum of Science, and enjoy breathtaking views from Skywalk Observatory.

To find reviews, other places to visit, more things to do, and tourist information, you can read our Boston trip planner.

Hyderabad, India to Boston is an approximately 20-hour flight. The time zone difference when traveling from Hyderabad to Boston is minus 10.5 hours. Expect cooler temperatures when traveling from Hyderabad in November; daily highs in Boston reach 13°C and lows reach 3°C. Wrap up your sightseeing on the 3rd (Tue) early enough to fly to Provincetown.

Things to do in Boston

Museums · Historic Sites · Parks · Childrens Museums

Side Trips

Provincetown

— 5 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Venture out of the city with trips to Eastham (Coast Guard Beach, Nauset Light Beach, &more), Atwood Museum (in Chatham) and Nauset Beach (in Orleans). There's still lots to do: kick back and relax at Herring Cove Beach, stroll through Race Point Beach, browse the exhibits of Provincetown Town Hall, and trek along Cape Cod Provincelands Trail.

Plan a trip to Provincetown easily and quickly by telling Inspirock to suggest an itinerary.

You can fly from Boston to Provincetown in 2 hours. Alternatively, you can ride a ferry; or drive. In December, daytime highs in Provincetown are 7°C, while nighttime lows are 1°C. Wrap up your sightseeing on the 8th (Sun) to allow time to drive to Sandwich.

Things to do in Provincetown

Parks · Outdoors · Beaches · Museums

Side Trips

Sandwich

— 3 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Explore Sandwich's surroundings by going to Yarmouth Port (Captain Bangs Hallet House Museum & Edward Gorey House), Chatham (Monomoy National Wildlife Refuge & Chatham Lighthouse Beach) and Chatham Marconi Maritime Center (in North Chatham). And it doesn't end there: explore the world behind art at Sandwich Glass Museum, examine the collection at Heritage Museums & Gardens, grab your bike and head to Shining Sea Bikeway, and don't miss a visit to Old King's Hwy.

For more things to do, traveler tips, other places to visit, and more tourist information, refer to the Sandwich trip itinerary builder.

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. December in Sandwich sees daily highs of 9°C and lows of -1°C at night. Finish up your sightseeing early on the 11th (Wed) so you can travel to Oak Bluffs.

Things to do in Sandwich

Museums · Parks · Historic Sites · Outdoors

Side Trips

Oak Bluffs, Martha's Vineyard

— 2 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. On the 12th (Thu), browse the collection at West Tisbury Free Public Library, then get lost in a book at Edgartown Public Library, then visit a coastal fixture at Edgartown Lighthouse, and finally tee off at Farm Neck Golf Club. On the 13th (Fri), you'll have a packed day of sightseeing: steep yourself in history at Trinity Park Tabernacle, then admire the natural beauty at Mytoi, then stop by Chilmark Chocolates, and finally wander the streets of Martha's Vineyard Camp meeting Association (MVCMA).

For where to stay, photos, maps, and more tourist information, use the Oak Bluffs trip itinerary builder site.

You can do a combination of taxi and ferry from Sandwich to Oak Bluffs in 1.5 hours. Alternatively, you can do a combination of bus and ferry. Expect a daytime high around 9°C in December, and nighttime lows around -1°C. Wrap up your sightseeing on the 13th (Fri) early enough to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Historic Sites · Golf · Neighborhoods · Shopping

Side Trips

Nantucket

— 5 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, and historic sites. Your trip includes some of its best attractions: examine the collection at Whaling Museum, get to know the fascinating history of Milestone Bog, make a trip to Nantucket Founders Burial Ground, and see the sky in a new way at Loines Observatory.

To find other places to visit, traveler tips, ratings, and tourist information, read Nantucket road trip planning site.

You can ride a ferry from Oak Bluffs to Nantucket in 2 hours. December in Nantucket sees daily highs of 9°C and lows of 1°C at night. Finish up your sightseeing early on the 18th (Wed) so you can catch the flight to New York City.

Things to do in Nantucket

Historic Sites · Museums · Parks · Outdoors

New York City

— 10 nights

Big Apple

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 trip includes some of its best attractions: enjoy breathtaking views from Empire State Building, pause for some photo ops at 9/11 Memorial, stroll through Central Park, and explore the world behind art at The Metropolitan Museum of Art.

To find other places to visit, more things to do, and tourist information, you can read our New York City day trip planning tool.

You can fly from Nantucket to New York City in 3 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, bus, and train. Expect a daytime high around 10°C in December, and nighttime lows around 2°C. Finish up your sightseeing early on the 28th (Sat) so you can catch the train to Philadelphia.

Things to do in New York City

Museums · Parks · Historic Sites · Neighborhoods

Side Trip

Philadelphia

— 9 nights

The City of Brotherly Love

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S. democracy, as it was once the meeting place for the country's Founding Fathers.
Change things up with these side-trips from Philadelphia: Hagley Museum And Library (in Wilmington), Winterthur Museum, Garden & Library (in Winterthur) and Longwood Gardens (in Kennett Square). There's lots more to do: stroll around Wissahickon Valley Park, get engrossed in the history at Eastern State Penitentiary, get your game on at Urban Axes Philadelphia, and explore the world behind art at Philadelphia Museum of Art.

For maps, more things to do, traveler tips, and other tourist information, use the Philadelphia trip planner.

You can take a train from New York City to Philadelphia in 1.5 hours. Alternatively, you can drive; or take a bus. In December, plan for daily highs up to 10°C, and evening lows to 1°C. Cap off your sightseeing on the 6th (Mon) early enough to catch the flight back home.

Things to do in Philadelphia

Museums · Parks · Historic Sites · Nature

Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.