Experience 5 Days in Massachusetts

How to See Massachusetts in Five Days

John W. Weeks Bridge, Dunster House, Havard University, Cambridge, Boston, Massachusetts, America
joe daniel price / Getty Images

Planning a trip to Massachusetts? No state in the U.S. is home to more symbolic sites, none more steeped in the 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. 

But 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 (America's oldest continuously operating restaurant, Union Oyster House, is one option), and 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 day two of your Massachusetts stay, take the morning to tour the Harvard University campus in Cambridge. The oldest institution of higher education in the U.S. has many fascinating museums that are open to the public, too. Return to downtown Boston for lunch at Cheers Boston. The former Bull & Finch Pub was the inspiration for the television show Cheers.

After lunch, take 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 "Green Monster."

Carousel in Boston Public Gardens
Violet Smirnova / TripSavvy

Day Three

In season, depart on day three from Boston via passenger ferry for a day in Provincetown on Cape Cod. It's just a 90-minute crossing and is very scenic along the 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 the town's main thoroughfare, Commercial Street, and wander in and out of 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 reliving the American Revolution at Minute Man National Historical Park. Also visit Walden Pond State Reservation, 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 overall 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. Or choose one of these other fun things to do on the Massachusetts North Shore.

Tips for Your Massachusetts Trip

Before you jet off to Beantown, it's best to brush up on a few local tips.

  • Accommodations right in Boston tend to be on the pricey side. You may wish to look for less expensive options in city suburbs.
  • Boston is a walking city! Wear comfortable shoes, and be sure to bring boots along on winter visits. It is also easy to navigate around Boston using the "T": Boston's subway system.
  • You won't need a car in Boston, and you're better off without one. It's not the easiest city to drive in, and parking is expensive. Once you leave to explore other areas of Massachusetts, however, you'll want the freedom having a car allows.
  • If you're visiting Massachusetts in the fall, consider basing yourself in Boston and filling your itinerary with day trips so you can see the gorgeous foliage.