Boston in 2-3 Days

The most obvious itinerary is the Freedom Trail, a 2.5-mile path connecting 16 historic areas in Boston, which in itself could take a whole weekend or more to complete. Maps and information are available at the kiosk in the Commons near the Park Street T stop, and costumed tour guides lurk around the area during the warm months.

Day One

Start the day with a morning stroll through the Boston Commons and Public Gardens, then down Newbury Street or parallel Commonwealth Avenue, Marlborough St. or Beacon St. for a look at the gorgeous Back Bay. Turn left towards Boylston Street where the Prudential Center’s 50th floor Skywalk offers 360-degree views of the city. Exit onto Huntington Avenue towards the Museum of Fine Arts or head back up to Commonwealth Ave to Fenway Park in Kenmore Square for a Red Sox game. If tickets are out of reach or out of season, watch a game with fans at one of the area’s sports bars. On nearby Lansdowne St., nightclubs host DJ’s and live bands every night.

Day Two

Start the day taking in the North End before heading south to explore the many attractions in the historic heart of Boston. Continue south through Downtown Crossing and stop by Filene’s Basement. Enjoy the sights and smells, and especially the tastes, of Chinatown on your way to see a play in the theatre district; discounted same-day tickets are available at many venues and at the Bostix kiosk in Copley Square. Get a drink after the show either here or in the nearby South End.


Boston in One Week:

A little extra time allows visitors to enjoy more outside of the immediate downtown area.

  • In Cambridge, check out Central and Harvard Squares, two areas known for their funky shops, restaurants and music venues. In Harvard Square, listen to folk music at Club Passim, where Bob Dylan and Joan Baez once played, or visit Harvard University’s small but impressive museums, such as the Fogg Art Museum.
  • At the Garment District in Kendal Square in Cambridge, dig on your hands and knees through a pile of used clothes in their “Dollar-A-Pound” section.
  • In Brookline, eat at a Jewish deli and watch an independent film at the historic art deco Coolidge Corner Theatre.
  • Charlestown, north of the city, has more history to take in at the Bunker Hill Monument and the USS Constitution, a restored 18th century warship.
  • If museums are your thing, in addition to the Museum of Fine Arts are the Museum of Science and the New England Aquarium, as well as smaller offerings such as the Isabelle Stewart Gardner Art Museum, the JFK Library and Museum and the Franklin Park Zoo.