5 days in Massachusetts Itinerary

5 days in Massachusetts Itinerary

Created using Inspirock Massachusetts travel planner

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Route & dates

5 days in Massachusetts Itinerary

Start: Toronto
ferry + Fly:  4​h
1
Provincetown
— Few hours
Drive:  4​h 30​min
2
Lenox
— 1 night
Drive:  2​h 30​min
3
Boston
— 3 nights
Fly + ferry:  4​h 30​min
End: Toronto


Learn more about your trip

few
hours
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.
On the 31st (Fri), enjoy the sand and surf at Race Point Beach and then examine the collection at Pilgrim Monument & Provincetown Museum.

To see reviews, other places to visit, more things to do, and more tourist information, you can read our Provincetown journey planner .

Toronto, Canada to Provincetown is an approximately 4-hour flight. You can also drive; or take a bus. May in Provincetown sees daily highs of 20°C and lows of 10°C at night. Wrap up your sightseeing on the 31st (Fri) early enough to drive to Lenox.

Things to do in Provincetown

Beaches Parks Outdoors
Highlights from your plan
Race Point Beach ©
Race Point Beach

1
night
Lenox

Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. On the 1st (Sat), take your sightseeing to a higher altitude at Lenox Mountain, then learn about winemaking at Balderdash Cellars, then explore the world behind art at Norman Rockwell Museum, and finally see the interesting displays at Bidwell House Museum.

To find more things to do, ratings, where to stay, and other tourist information, use the Lenox trip itinerary tool .

Traveling by car from Provincetown to Lenox takes 4.5 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of flight and bus. In May, plan for daily highs up to 23°C, and evening lows to 8°C. Finish up your sightseeing early on the 1st (Sat) so you can go by car to Boston.

Things to do in Lenox

Nature Museums Parks

Side Trips

Bidwell House Museum, Balderdash Cellars, Norman Rockwell Museum
Highlights from your plan
Lenox Mountain ©
Lenox Mountain
Norman Rockwell Museum ©
Norman Rockwell Museum
Bidwell House Museum ©
Bidwell House Museum

3
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.
Boston is known for historic sites, museums, parks, shopping, and nightlife. Your plan includes some of its best attractions: admire all the interesting features of Fenway Park, browse the different shops at Faneuil Hall Marketplace, don't miss a visit to Boston Public Library, and admire the masterpieces at Museum of Fine Arts.

To find maps and more tourist information, go to the Boston online visit planner .

You can drive from Lenox to Boston in 2.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Lenox in June, you can expect nighttime temperatures to be somewhat warmer in Boston, with lows of 18°C. Wrap up your sightseeing on the 4th (Tue) early enough to travel back home.

Things to do in Boston

Museums Parks Historic Sites
Highlights from your plan
Freedom Trail ©
Freedom Trail
Fenway Park ©
Fenway Park
Museum of Fine Arts ©
Museum of Fine Arts

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