Planning a trip to Massachusetts? No state in the U.S. is home to more symbolic sites, none more steeped in American patriotic tradition. You’ll want to start in Boston, of course. You could easily spend five days seeing the top attractions in Massachusetts’ historic and dynamic capital city.
However, what if you only have five days total to spend in Massachusetts? Here is a suggested itinerary for seeing the best Massachusetts highlights in just five days.
Day One
Spend a half-day getting to know Boston, either by walking the Freedom Trail, which connects landmark sites, or by taking a Duck Tour. Have lunch at Quincy Market, where America’s oldest continuously operating restaurant, Union Oyster House, is one option. Spend the afternoon at one of the city’s spectacular museums, such as the Museum of Fine Arts, Boston or the Museum of Science, Boston.
Day Two
On the second day of your Massachusetts adventure, take the morning to tour the Harvard University campus in Cambridge, the oldest institution of higher education in the U.S. The campus hosts many fascinating museums that are open to the public. Return to downtown Boston for lunch at Cheers Boston, the former Bull & Finch Pub that inspired the television show Cheers.
After lunch, consider taking a swan boat ride in the Boston Public Garden, then visit another of the city’s museums, shop for antiques on Beacon Hill, or tour historic Fenway Park, home of the Boston Red Sox and the famous “Green Monster.”
Day Three
During the season, depart on day three from Boston via passenger ferry for a day in Provincetown on Cape Cod. It’s just a 90-minute scenic crossing along the beautiful coast. Visit the Pilgrim Monument, which marks the site of the Pilgrims’ first landing in the New World, or see the famous dunes of the cape with Art’s Dune Tours. Stroll Commercial Street, the town’s main thoroughfare, and explore its shops, galleries, and restaurants before returning to Boston by ferry at the end of the day.
Day Four
Rent a car and drive northwest to Concord, Massachusetts, and spend time revisiting the American Revolution at Minute Man National Historical Park. Also, visit Walden Pond State Reservation, the former well-known home of Henry David Thoreau.
Day Five
Spend your last morning taking in some of the spooky sights in Salem, Massachusetts. The Salem Witch Museum provides the best orientation to the drama surrounding the 1692 witch hysteria for which the city is notorious. In the afternoon, drive farther north along the coast and visit Rocky Neck, America’s first art colony, in Gloucester. Alternatively, choose from other enjoyable activities in the Massachusetts North Shore.
Tips for Your Massachusetts Trip
Before heading to Beantown, it’s beneficial to brush up on a few local tips:
- Accommodations in Boston tend to be on the pricey side. You may want to explore less expensive options in city suburbs.
- Boston is a walking city! Wear comfortable shoes and bring boots during winter visits. It is also easy to navigate using the “T”, Boston’s subway system.
- A car isn’t necessary in Boston; it’s not the easiest city to drive in, and parking can be expensive. However, when exploring other areas of Massachusetts, having a car will grant you more freedom.
- If you’re visiting Massachusetts in the fall, consider basing yourself in Boston and filling your itinerary with nearby day trips to experience the stunning foliage.
