59 days in Massachusetts Itinerary

59 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary planner
Make it your trip
Fly to Bradley International Airport, Drive to Williamstown
1
Williamstown
— 8 nights
Drive
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Westfield
— 9 nights
Drive
3
Sandwich
— 9 nights
Taxi to Hyannis, MA, Ferry to Nantucket
4
Nantucket
— 10 nights
Ferry to Hyannis, MA, Taxi to Provincetown
5
Provincetown
— 10 nights
Fly
6
Boston
— 10 nights
Fly

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Williamstown — 8 nights

Williamstown is a town in Berkshire County, in the northwest corner of Massachusetts, United States. Explore Williamstown's surroundings by going to Notchview (in Windsor), Charlemont (Bissell Covered Bridge, A.L. Avery & Son General Store, &more) and Pittsfield (Herman Melville's Arrowhead, Balderdash Cellars, &more). There's much more to do: admire the masterpieces at The Clark Art Institute, hit the slopes at Jiminy Peak Mountain Resort, take in the awesome beauty at Mount Greylock, and identify plant and animal life at Mountain Meadow Preserve.

For where to stay, reviews, maps, and tourist information, use the Williamstown trip planner.

Sao Paulo, Brazil to Williamstown is an approximately 25-hour combination of flight and car. Traveling from Sao Paulo to Williamstown, you'll gain 2 hours due to the time zone difference. In March, Williamstown is cooler than Sao Paulo - with highs of 5°C and lows of -6°C. Cap off your sightseeing on the 10th (Sun) early enough to go by car to Westfield.
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Parks · Nature · Outdoors · Winter Sports
Side Trips
Find places to stay Mar 2 — 10:

Westfield — 9 nights

Westfield is a city in Hampden County, in the Pioneer Valley of western Massachusetts, United States. Get out of town with these interesting Westfield side-trips: Fenway Golf (in East Longmeadow), Rock House Reservation (in West Brookfield) and Peaked Mountain (in Monson). And it doesn't end there: walk around Stanley park, browse the different shops at Thornes Marketplace, identify plant and animal life at Arcadia Wildlife Sanctuary, and take in the dramatic scenery at Bear's Den.

To see reviews, more things to do, where to stay, and other tourist information, you can read our Westfield trip itinerary planner.

You can drive from Williamstown to Westfield in 1.5 hours. March in Westfield sees daily highs of 7°C and lows of -4°C at night. Finish your sightseeing early on the 19th (Tue) so you can drive to Sandwich.
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Parks · Nature · Wildlife · Shopping
Side Trips
Find places to stay Mar 10 — 19:

Sandwich — 9 nights

Sandwich is a town in Barnstable County, Massachusetts, United States. You'll find plenty of places to visit near Sandwich: Nobska Point Lighthouse (in Woods Hole), Falmouth (Shining Sea Bikeway, Spohr Gardens, &more) and Yarmouth Port (Captain Bangs Hallet House Museum & Edward Gorey House). There's still lots to do: examine the collection at Heritage Museums & Gardens, pause for some photo ops at Plymouth Rock, get engrossed in the history at Plimoth Patuxet Museums, and pause for some serene contemplation at St. Anthony of Padua Church.

To find traveler tips, maps, and tourist information, read our Sandwich trip itinerary planner.

Traveling by car from Westfield to Sandwich takes 2.5 hours. In March, plan for daily highs up to 7°C, and evening lows to -3°C. Cap off your sightseeing on the 28th (Thu) early enough to travel to Nantucket.
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Parks · Outdoors · Museums · Beaches
Side Trips
Find places to stay Mar 19 — 28:

Nantucket — 10 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: visit a coastal fixture at Great Point Light, browse the collection at Nantucket Atheneum, see the sky in a new way at Loines Observatory, and look for all kinds of wild species at Coskata-Coatue Wildlife Refuge.

To see where to stay, other places to visit, and tourist information, use the Nantucket itinerary builder site.

Do a combination of taxi and ferry from Sandwich to Nantucket in 2 hours. Alternatively, you can do a combination of bus and ferry. March in Nantucket sees daily highs of 7°C and lows of 0°C at night. Wrap up your sightseeing on the 7th (Sun) early enough to travel to Provincetown.
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Parks · Outdoors · Beaches · Historic Sites
Find places to stay Mar 28 — Apr 7:

Provincetown — 10 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.
Get out of town with these interesting Provincetown side-trips: Eastham (Salt Pond Visitor Center, Captain Penniman House, &more), Orleans (Nauset Beach & Church Of The Transfiguration) and Nickerson State Park (in Brewster). There's lots more to do: kick back and relax at Race Point Beach, browse the collection at Provincetown Library, hike along Cape Cod Rail Trail, and take in the waterfront at MacMillan Wharf.

To find photos, maps, other places to visit, and tourist information, go to the Provincetown trip builder tool.

Getting from Nantucket to Provincetown by combination of ferry and taxi takes about 3 hours. Other options: do a combination of ferry and bus. Expect a daytime high around 12°C in April, and nighttime lows around 4°C. Finish up your sightseeing early on the 17th (Wed) so you can catch the flight to Boston.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Apr 7 — 17:

Boston — 10 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.
Venture out of the city with trips to Salem (Peabody Essex Museum & The House of the Seven Gables) and Cogswell's Grant (in Essex). The adventure continues: explore the world behind art at Museum of Fine Arts, take in the spiritual surroundings of Trinity Church, appreciate the extensive heritage of Freedom Trail, and browse the different shops at Faneuil Hall Marketplace.

To find traveler tips, other places to visit, photos, and more tourist information, refer to the Boston tour builder.

You can fly from Provincetown to Boston in 2 hours. Alternatively, you can ride a ferry; or drive. April in Boston sees daily highs of 15°C and lows of 5°C at night. Cap off your sightseeing on the 27th (Sat) early enough to catch the flight back home.
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Museums · Historic Sites · Parks · Shopping
Side Trips
Find places to stay Apr 17 — 27:

Massachusetts travel guide

4.3
History Museums · Nightlife · Art Museums
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.
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