18 days in Massachusetts Itinerary

18 days in Massachusetts Itinerary

Created using Inspirock Massachusetts route maker
Make it your trip
Fly
1
Lenox
— 3 nights
Drive
2
Boston
— 6 nights
Fly
3
Provincetown
— 4 nights
Drive
4
Sandwich
— 4 nights
Fly

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Lenox — 3 nights

Lenox is an affluent town in Berkshire County, Massachusetts, United States. Explore the numerous day-trip ideas around Lenox: Polish Center of Discovery and Learning (in Chicopee), Adams (Ashuwillticook Rail Trail & Mount Greylock) and MASS MoCA (in North Adams). And it doesn't end there: admire the masterpieces at Norman Rockwell Museum, get engrossed in the history at Hancock Shaker Village, browse the exhibits of The Mount, Edith Wharton's Home, and take in the awesome beauty at Monument Mountain.

Plan a Lenox trip in moments using our itinerary builder.

Fort Myers to Lenox is an approximately 5-hour flight. You can also drive; or take a bus. Prepare for colder weather when traveling from Fort Myers in October: high temperatures in Lenox hover around 60°F and lows are around 40°F. Wrap up your sightseeing on the 14th (Fri) to allow time to drive to Boston.
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Museums · Parks · Nature · Outdoors
Side Trips

Boston — 6 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 the numerous day-trip ideas around Boston: Salem (Peabody Essex Museum, Pickering Wharf, &more). There's still lots to do: take in nature's colorful creations at Boston Public Garden, traverse land and water with a duck tour, explore the world behind art at Isabella Stewart Gardner Museum, and take an in-depth tour of John F. Kennedy Presidential Museum & Library.

For more things to do, photos, other places to visit, and tourist information, you can read our Boston trip builder.

Traveling by car from Lenox to Boston takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Lenox in October, plan for somewhat warmer nights in Boston, with lows around 50°F. Cap off your sightseeing on the 20th (Thu) early enough to catch the flight to Provincetown.
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Museums · Parks · Historic Sites · Neighborhoods
Side Trips

Provincetown — 4 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.
You'll find plenty of places to visit near Provincetown: Nauset Beach (in Orleans) and Eastham (Salt Pond Visitor Center & Nauset Light Beach). Spend the 22nd (Sat) exploring nature at Cape Cod National Seashore. There's still lots to do: pause for some photo ops at Pilgrim Monument & Provincetown Museum, look for all kinds of wild species at Art's Dune Tours, trek along Cape Cod Provincelands Trail, and tour the pleasant surroundings at Race Point Beach.

To see maps, other places to visit, more things to do, and more tourist information, refer to the Provincetown trip builder.

Fly from Boston to Provincetown in 2 hours. Alternatively, you can ride a ferry; or drive. In October, plan for daily highs up to 63°F, and evening lows to 49°F. Wrap up your sightseeing on the 24th (Mon) to allow time to drive to Sandwich.
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Outdoors · Parks · Beaches · Nature
Side Trips

Sandwich — 4 nights

Sandwich is a town in Barnstable County, Massachusetts, United States. Explore Sandwich's surroundings by going to Stone Bridge Farm (in Acushnet), Shining Sea Bikeway (in Falmouth) and New Bedford Whaling Museum (in New Bedford). Next up on the itinerary: get engrossed in the history at Sandwich Glass Museum, relax in the rural setting at Coonamessett Farm, examine the collection at Heritage Museums & Gardens, and appreciate the history behind Plymouth Rock.

To find traveler tips, maps, ratings, and other tourist information, read our Sandwich trip tool.

You can drive from Provincetown to Sandwich in 1.5 hours. Alternatively, you can take a bus. In October, daytime highs in Sandwich are 64°F, while nighttime lows are 46°F. Wrap up your sightseeing on the 28th (Fri) to allow time to fly back home.
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Museums · Outdoors · Tours · Wildlife
Side Trips

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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