60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

Plan created by another user. Make it yours
Fly
1
Boston
— 10 nights
Drive
2
Stockbridge
— 9 nights
Drive
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Sandwich
— 10 nights
Drive
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Oak Bluffs, Martha's Vineyard
— 9 nights
Ferry
5
Nantucket
— 10 nights
Ferry to Hyannis, MA, Taxi to Provincetown
6
Provincetown
— 9 nights
Drive to General Edward Lawrence Logan International Airport, Fly to Porto Seguro Airport

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10
nights
Boston

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.
Explore the numerous day-trip ideas around Boston: Nantasket Beach (in Hull), Concord (Louisa May Alcott's Orchard House, Walden Pond State Reservation, &more) and Salem (Peabody Essex Museum & The House of the Seven Gables). Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, stroll around Boston Common, see where the action happens at Fenway Park, and appreciate the extensive heritage of Freedom Trail.

To find ratings, reviews, traveler tips, and tourist information, you can read our Boston travel route app.

Porto Seguro, Brazil to Boston is an approximately 23-hour flight. The time zone changes from Brasilia Standard Time (BRT) to Eastern Standard Time (EST), which is usually a -2 hour difference. Plan for cooler temperatures traveling from Porto Seguro in December, with highs in Boston at 7°C and lows at 0°C. Finish your sightseeing early on the 12th (Wed) to allow enough time to drive to Stockbridge.

Things to do in Boston

Museums · Parks · Historic Sites · Outdoors

Side Trips

9
nights
Stockbridge

Stockbridge is a town in Berkshire County in western Massachusetts, United States. Venture out of the city with trips to Mount Tom State Reservation (in Holyoke), Stanley park (in Westfield) and Peaked Mountain (in Monson). There's still lots to do: stroll around Forest Park, fly down the slopes at Jiminy Peak Mountain Resort, get your game on at Fenway Golf, and take your sightseeing to a higher altitude at Mount Greylock.

To see where to stay, more things to do, and tourist information, refer to the Stockbridge road trip planning tool.

Traveling by car from Boston to Stockbridge takes 2.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Boston in December, things will get little chillier in Stockbridge: highs are around 3°C and lows about -5°C. Finish your sightseeing early on the 21st (Fri) to allow enough time to drive to Sandwich.

Things to do in Stockbridge

Parks · Nature · Outdoors · Winter Sports

Side Trips

10
nights
Sandwich

Sandwich is a town in Barnstable County, Massachusetts, United States. Explore Sandwich's surroundings by going to Chatham (Chatham Lighthouse Beach, Ducks in the Window, &more), Cranberry Valley Golf Course (in Harwich) and Brown's Bank (in Plymouth). There's much more to do: see the interesting displays at Heritage Museums & Gardens, enjoy the sand and surf at Corporation Beach, don't miss a visit to Old King's Hwy, and pause for some photo ops at Plymouth Rock.

To see more things to do, other places to visit, photos, and tourist information, use the Sandwich attractions planner.

Drive from Stockbridge to Sandwich in 3.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In December, Sandwich is a bit warmer than Stockbridge - with highs of 9°C and lows of -1°C. Finish your sightseeing early on the 31st (Mon) so you can drive to Oak Bluffs.

Things to do in Sandwich

Parks · Outdoors · Beaches · Museums

Side Trips

9
nights
Oak Bluffs, Martha's Vineyard

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. You'll find plenty of places to visit near Oak Bluffs: Falmouth (Shining Sea Bikeway & Old Silver Beach), Menemsha Public Beach (in Menemsha) and Chilmark (Menemsha Hills & Lucy Vincent Beach). There's much more to do: tee off at Farm Neck Golf Club, enjoy the sea views from Gay Head Lighthouse, admire the striking features of Trinity Park Tabernacle, and meet the residents at Woods Hole Science Aquarium.

To see reviews, maps, and tourist information, refer to the Oak Bluffs trip planner.

You can drive from Sandwich to Oak Bluffs in 1.5 hours. In December, daily temperatures in Oak Bluffs can reach 9°C, while at night they dip to -1°C. Wrap up your sightseeing on the 9th (Wed) early enough to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Parks · Outdoors · Beaches · Historic Sites

Side Trips

10
nights
Nantucket

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 plan includes some of its best attractions: see the interesting displays at Whaling Museum, don't miss a visit to Nantucket Founders Burial Ground, admire the natural beauty at Oldest House (Jethro Coffin House) and Kitchen Garden, and enjoy the sea views from Brant Point Lighthouse.

For ratings, photos, traveler tips, and tourist information, use the Nantucket trip planner.

Ride a ferry from Oak Bluffs to Nantucket in 2 hours. January in Nantucket sees daily highs of 5°C and lows of -2°C at night. Finish your sightseeing early on the 19th (Sat) so you can travel to Provincetown.

Things to do in Nantucket

Parks · Outdoors · Beaches · Historic Sites

9
nights
Provincetown

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.
Explore Provincetown's surroundings by going to Orleans (Nauset Beach & Church of the Transfiguration), Nickerson State Park (in Brewster) and Eastham (Nauset Light Beach & Coast Guard Beach). And it doesn't end there: see the interesting displays at Provincetown Art Association and Museum, don't miss a visit to Commercial Street, pause for some photo ops at Pilgrim Monument & Provincetown Museum, and hike along Cape Cod Rail Trail.

To see ratings, more things to do, photos, and more tourist information, you can read our Provincetown trip maker site.

Traveling by combination of ferry and taxi from Nantucket to Provincetown takes 3 hours. Alternatively, you can do a combination of ferry and bus. In January, daytime highs in Provincetown are 3°C, while nighttime lows are -3°C. Wrap up your sightseeing by early afternoon on the 28th (Mon) to allow enough time to travel back home.

Things to do in Provincetown

Outdoors · Parks · Beaches · Trails

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.