35 days in Massachusetts Itinerary

35 days in Massachusetts Itinerary

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Route & dates

35 days in Massachusetts Itinerary

Start: Washington DC
Fly:  3 h
1
Boston
— 8 nights
Drive:  2 h 30 min
2
Stockbridge
— 6 nights
Drive:  3 h 15 min
3
Sandwich
— 6 nights
Drive:  1 h 15 min
4
Provincetown
— 7 nights
Drive:  3 h 15 min
5
Nantucket
— 7 nights
Fly:  5 h 15 min
End: Washington DC

8
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 find plenty of places to visit near Boston: The Fairbanks House (in Dedham), The Needham Free Public Library (in Needham) and Salem (Peabody Essex Museum, The House of the Seven Gables, & more). Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, take a tour of Boston Tea Party Ships & Museum, appreciate the extensive heritage of Freedom Trail, and stroll around Boston Common.

For maps, photos, and tourist information, read our Boston online route planner .

Washington DC to Boston is an approximately 3-hour flight. You can also do a combination of train and flight; or drive. Prepare for little chillier weather when traveling from Washington DC in December: high temperatures in Boston hover around 43°F and lows are around 31°F. Finish your sightseeing early on the 30th (Mon) to allow enough time to drive to Stockbridge.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Cambridge, The Needham Free Public Library, Beanstalk Adventure Ropes Course, The Fairbanks House
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Boston Common ©
Boston Common

6
nights
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. You'll find plenty of places to visit near Stockbridge: Ashuwillticook Rail Trail (in Adams), Stanley park (in Westfield) and Maple Corner Farm Cross Country Ski Area (in Granville). There's much more to do: explore the world behind art at Norman Rockwell Museum, take your sightseeing to a higher altitude at Lenox Mountain, glide through natural beauty at Notchview, and do a tasting at Balderdash Cellars.

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

You can drive from Boston to Stockbridge in 2.5 hours. Other options are to take a bus; or take a train. Traveling from Boston in December, things will get slightly colder in Stockbridge: highs are around 37°F and lows about 23°F. Finish your sightseeing early on the 5th (Sun) so you can drive to Sandwich.

Things to do in Stockbridge

Parks Museums Outdoors

Side Trips

Lenox, Pittsfield, Otis Ridge, Ashuwillticook Rail Trail, Bullitt Reservation
Highlights from your plan
Stanley park ©
Stanley park
Norman Rockwell Museum ©
Norman Rockwell Museum
The Clark Art Institute ©
The Clark Art Institute

6
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. You'll find plenty of places to visit near Sandwich: Falmouth (Falmouth Museums on the Green & Cornelia Carey Sanctuary (The Knob)), Lizzie Borden House (in Fall River) and Chatham (Chatham Lighthouse Beach & Monomoy National Wildlife Refuge). The adventure continues: examine the collection at Heritage Museums & Gardens, grab your bike and head to Shining Sea Bikeway, admire the landmark architecture of Trinity Park Tabernacle, and steep yourself in history at Edward Gorey House.

To see traveler tips, reviews, and more tourist information, refer to the Sandwich journey builder .

Traveling by car from Stockbridge to Sandwich takes 3.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. Traveling from Stockbridge in January, expect Sandwich to be a bit warmer, temps between 39°F and 22°F. Wrap up your sightseeing on the 11th (Sat) to allow time to drive to Provincetown.

Things to do in Sandwich

Parks Museums Outdoors

Side Trips

Falmouth, Plymouth, Yarmouth Port, Chatham, Samuell Day Gallery
Highlights from your plan
Monomoy National Wildlife Refuge ©
Monomoy National Wildlife Refuge
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum

7
nights
Provincetown

Provincetown ©
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: Nauset Beach (in Orleans), Eastham (Coast Guard Beach, Salt Pond Visitor Center, & more) and Chatham (Atwood Museum, Chatham Railroad Museum, & more). And it doesn't end there: kick back and relax at Cape Cod National Seashore, tour the pleasant surroundings at Long Point, get interesting insight from Tours, and don't miss a visit to Commercial Street.

To see other places to visit, reviews, photos, and more tourist information, read Provincetown trip planner .

Drive from Sandwich to Provincetown in 1.5 hours. Alternatively, you can take a bus. In January, daytime highs in Provincetown are 38°F, while nighttime lows are 27°F. Finish your sightseeing early on the 18th (Sat) to allow enough time to drive to Nantucket.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Eastham, Chatham, Wellfleet, Nauset Beach, Cape Cod National Seashore
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Pilgrim Monument & Provincetown Museum ©
Race Point Beach ©
Race Point Beach

7
nights
Nantucket

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, historic sites, breweries & distilleries, and outdoors. Your plan includes some of its best attractions: examine the collection at Whaling Museum, take some stellar pictures from First Congregational Church, don't miss a visit to Nantucket Founders Burial Ground, and tour the pleasant surroundings at Jetties Beach.

To find maps, more things to do, photos, and other tourist information, read our Nantucket trip maker website .

Getting from Provincetown to Nantucket by car takes about 3.5 hours. In January, daily temperatures in Nantucket can reach 40°F, while at night they dip to 28°F. Finish your sightseeing early on the 25th (Sat) to allow enough time to travel back home.

Things to do in Nantucket

Historic Sites Parks Outdoors
Highlights from your plan
Great Point Light ©
Great Point Light
Whaling Museum ©
Whaling Museum
Jetties Beach ©
Jetties Beach

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