Boston fits colonial-era streets, universities and a working harbor into a small city you can cover on foot and by the T. Back Bay and Downtown are the easy first-visit bases. Pick the Seaport or Fenway when you have a reason to be there, like a convention or a game.
Walk the Freedom Trail from Boston Common through Downtown and the North End to Charlestown. Its stops include Faneuil Hall, the Old North Church and the USS Constitution. If the trail and the harbor ferries are your main plans, a Downtown hotel saves time.
Back Bay has Copley Square, the Boston Public Library and Newbury Street. Beacon Hill lies across the Common, with brick houses and shops along Charles Street. Both are good to walk, but Beacon Hill’s slopes and old sidewalks are hard work with a suitcase.
Across the Fort Point Channel, the Seaport has the convention center, waterfront paths and the Institute of Contemporary Art. Fenway has the ballpark and the Museum of Fine Arts. Cambridge, across the Charles River, has Harvard and MIT. It is a separate city, so if your sights are in Boston, look at the T route before you book there.
Summer days are warm and sometimes humid. Winter can be snowy, and windy by the harbor. Spring weather changes fast. The T links many central districts, and Logan Airport is just across the harbor. If you drive, ask about the hotel’s parking rate and expect narrow one-way streets.