30 days in Massachusetts Itinerary

30 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary planner
Make it your trip
Fly
1
Lenox
— 4 nights
Drive
2
Boston
— 11 nights
Fly
3
Provincetown
— 5 nights
Drive
4
Hyannis
— 5 nights
Ferry
5
Nantucket
— 4 nights
Fly

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Lenox — 4 nights

Lenox is an affluent town in Berkshire County, Massachusetts, United States. Venture out of the city with trips to Pioneer Valley Food Tours (in Northampton), Mount Tom State Reservation (in Holyoke) and MASS MoCA (in North Adams). The adventure continues: admire the masterpieces at Norman Rockwell Museum, walk around Stanley park, shop like a local with Yankee Candle Flagship Store, and get engrossed in the history at The Mount, Edith Wharton's Home.

To see where to stay, traveler tips, reviews, and other tourist information, read Lenox trip itinerary maker site.

New York City to Lenox is an approximately 2.5-hour flight. You can also drive; or do a combination of train and bus. Expect slightly colder temperatures when traveling from New York City in November; daily highs in Lenox reach 47°F and lows reach 28°F. Finish up your sightseeing early on the 5th (Fri) so you can go by car to Boston.
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Museums · Parks · Nature · Wineries
Side Trips

Boston — 11 nights

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 Boston's surroundings by going to Salem (Salem Witch Trials Memorial, Salem Witch Museum, &more), Fishermen's Memorial Monument (in Gloucester) and Louisa May Alcott's Orchard House (in Concord). And it doesn't end there: admire the masterpieces at Museum of Fine Arts, get engrossed in the history at Boston Tea Party Ships & Museum, wander the streets of North End, and engage your brain at Museum of Science.

To find reviews, traveler tips, ratings, and tourist information, refer to the Boston trip itinerary planner.

You can drive from Lenox to Boston in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Lenox in November, Boston is a bit warmer at night with lows of 37°F. Wrap up your sightseeing on the 16th (Tue) early enough to fly to Provincetown.
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Museums · Historic Sites · Parks · Neighborhoods
Side Trips

Provincetown — 5 nights

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.
Change things up with these side-trips from Provincetown: Eastham (Captain Penniman House, Nauset Light Beach, &more). There's much more to do: enjoy the sand and surf at Herring Cove Beach, admire the masterpieces at Provincetown Art Association and Museum, do a tasting at Truro Vineyards of Cape Cod, and stroll through Corn Hill Beach.

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 November in Provincetown, expect temperatures between 51°F during the day and 39°F at night. Finish your sightseeing early on the 21st (Sun) to allow enough time to drive to Hyannis.
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Outdoors · Beaches · Parks · Nature
Side Trips

Hyannis — 5 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Get out of town with these interesting Hyannis side-trips: Plymouth (Plymouth Rock, Plimoth Pawtuxet, &more), Cape Cod Canal (in Buzzards Bay) and Chatham (Atwood Museum & Chatham Lighthouse Beach). There's still lots to do: examine the collection at New Bedford Whaling Museum, relax in the rural setting at Coonamessett Farm, take an in-depth tour of Sandwich Glass Museum, and stroll through Gray's Beach.

To find other places to visit, maps, where to stay, and more tourist information, use the Hyannis trip planner.

Drive from Provincetown to Hyannis in 1.5 hours. Alternatively, you can take a bus. November in Hyannis sees daily highs of 53°F and lows of 37°F at night. Finish your sightseeing early on the 26th (Fri) to allow enough time to ride a ferry to Nantucket.
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Museums · Outdoors · Parks · Historic Sites
Side Trips

Nantucket — 4 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: see the interesting displays at Whaling Museum, tee off at Miacomet Golf Club, take in the architecture and atmosphere at Nantucket United Methodist Church, and kick back and relax at Jetties Beach.

For maps, where to stay, other places to visit, and more tourist information, you can read our Nantucket trip planner.

Traveling by ferry from Hyannis to Nantucket takes 2 hours. Alternatively, you can fly. In November, daytime highs in Nantucket are 53°F, while nighttime lows are 41°F. Wrap up your sightseeing on the 30th (Tue) to allow time to fly back home.
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Historic Sites · Outdoors · Museums · Beaches

Massachusetts travel guide

4.3
History Museums · Art Museums · Nightlife
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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