30 days in Massachusetts Itinerary

30 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip builder

Make it your trip
Drive
1
Lenox
— 4 nights
Drive
2
Boston
— 12 nights
Fly
3
Provincetown
— 4 nights
Drive
4
Hyannis
— 6 nights
Ferry
5
Nantucket
— 3 nights
Fly

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Lenox

— 4 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Explore the numerous day-trip ideas around Lenox: Mount Tom State Reservation (in Holyoke), Springfield (William Pynchon Statue, Dr. Seuss National Memorial Sculpture Garden, &more) and Stanley park (in Westfield). The adventure continues: admire the masterpieces at Norman Rockwell Museum, see the interesting displays at Yankee Candle Flagship Store, contemplate the long history of The Mount, Edith Wharton's Home, and do a tasting at Balderdash Cellars.

To find photos, more things to do, and tourist information, go to the Lenox tour planner.

New York City to Lenox is an approximately 2.5-hour flight. You can also drive; or do a combination of train and bus. Prepare for slightly colder weather when traveling from New York City in November: high temperatures in Lenox hover around 47°F and lows are around 28°F. Wrap up your sightseeing on the 5th (Fri) early enough to drive to Boston.

Things to do in Lenox

Museums · Historic Sites · Parks · Wineries

Side Trips

Boston

— 12 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 Louisa May Alcott's Orchard House (in Concord), Fishermen's Memorial Monument (in Gloucester) and Salem (The House of the Seven Gables, Salem Witch Museum, &more). There's lots more to do: admire the masterpieces at Museum of Fine Arts, get engrossed in the history at John F. Kennedy Presidential Museum & Library, stroll around Boston Common, and stop by North End.

To see maps, where to stay, more things to do, and more tourist information, read Boston driving holiday planner.

Getting from Lenox to Boston by car takes about 2.5 hours. Other options: take a bus; or do a combination of bus and train. Plan for somewhat warmer nights when traveling from Lenox in November since evenings lows in Boston dip to 37°F. Finish your sightseeing early on the 17th (Wed) so you can fly to Provincetown.

Things to do in Boston

Museums · Historic Sites · Shopping · Parks

Side Trips

Provincetown

— 4 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 (Nauset Light Beach, Salt Pond Visitor Center, &more). The adventure continues: tour the pleasant surroundings at Herring Cove Beach, enjoy the sand and surf at Cape Cod National Seashore, admire the masterpieces at Provincetown Art Association and Museum, and learn about winemaking at Truro Vineyards of Cape Cod.

To find reviews, other places to visit, maps, and more tourist information, go to the Provincetown trip itinerary planner.

Traveling by flight from Boston to Provincetown takes 2 hours. Alternatively, you can ride a ferry; or drive. In November, daytime highs in Provincetown are 51°F, while nighttime lows are 39°F. Finish your sightseeing early on the 21st (Sun) to allow enough time to drive to Hyannis.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Hyannis

— 6 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Venture out of the city with trips to Plymouth (Mayflower II, Plymouth Rock, &more), Chatham (Atwood Museum, Chatham Lighthouse Beach, &more) and Cape Cod Canal (in Buzzards Bay). The adventure continues: see the interesting displays at New Bedford Whaling Museum, don't miss a visit to Old King's Hwy, kick back and relax at Gray's Beach, and pause for some serene contemplation at Old Whaling Church.

To see maps, more things to do, traveler tips, and tourist information, go to the Hyannis tour itinerary planner.

Drive from Provincetown to Hyannis in 1.5 hours. Alternatively, you can take a bus. In November, daily temperatures in Hyannis can reach 53°F, while at night they dip to 37°F. Finish up your sightseeing early on the 27th (Sat) so you can catch the ferry to Nantucket.

Things to do in Hyannis

Museums · Parks · Outdoors · Historic Sites

Side Trips

Nantucket

— 3 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 plan includes some of its best attractions: examine the collection at Whaling Museum, look and learn at Loines Observatory, play a few rounds at Miacomet Golf Club, and pause for some serene contemplation at Nantucket United Methodist Church.

To find traveler tips, reviews, ratings, and tourist information, read Nantucket trip itinerary builder.

You can ride a ferry from Hyannis to Nantucket in 2 hours. Another option is to fly. November in Nantucket sees daily highs of 53°F and lows of 41°F at night. Wrap up your sightseeing on the 30th (Tue) to allow time to fly back home.

Things to do in Nantucket

Historic Sites · Museums · Outdoors · Parks

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.