Make your first stop the city's first neighborhood: the North End, the perfect spot for an Italian fix. Load up on fresh pasta at Trattoria Il Panino (Parmenter and Hanover streets).
Skip the big museums. Cab it to the tiny Isabella Stewart Gardner Museum in the South End (280 Fenway; $12 entrance fee). The beautiful Venetian-style building houses an impressive but manageable-size collection of paintings (Matisse, Rembrandt, John Singer Sargent). The four empty frames are reminders of a high-profile--and still unsolved--1990 theft.
Wednesdays through Saturdays, take a 10-minute cab ride to the brewery named after Boston's own patriot brewer, Sam Adams (30 Germania St.; free). Tours include tastings of Extreme Utopia--Guinness record holder as the world's strongest beer.