Extending south and west of the Fenway, Brookline is a top contender for Boston's most desirable suburb—originally favored by landscape architects for its charming lanes, bucolic aspect and (in the mid-19th century) lack of pesky free-running animals, the town has attracted a slew of eminent residents through the years, from Frederick Law Olmsted to Barbara Walters, Tom Brady and Conan O'Brien. Brookline is also the birthplace of JFK and was the home of Artificial Intelligence guru, Marvin Minsky. Naturally enough, it's a great place to explore, hangout and chill, only a few short T stops from central Boston on the Green Line.
The flexible seafood menu is a big draw at Porto Maltese, which many locals regard as one of Boston's best Mediterranean eateries. Charcoal-grilled, flambéed, steamed or fried: the choice is yours, and the end result is always fantastic. Fans of Indian cuisine should check out Shan-A-Punjab, which has a terrific vegetarian platter on the appetizers menu, and a great baingan bharta (flamed grilled eggplant mashed with garlic, ginger and spices). FuGaKyu is the go-to spot for modern and traditional Japanese dishes.
Browsing becomes a fine art at Wild Goose Chase, which stocks a well-curated range of artisanal jewelry, hand-crafted home goods and gifts, from a Modern Moose monkey pendulum clock to Cody Blomberg prints of birds wearing hats. Brookline Booksmith will see you right for reading materials of all kinds, and has an excellent used-book cellar: on a recent search we noticed a 1926 edition of Hemingway's "The Sun Also Rises."
The extensive list of wines from Spain and South America makes Barcelona Wine Bar an essential watering hole, never mind the outstanding selection of tapas. Matt Murphy’s Pub gives the essential elements of the classic Irish pub a very congenial 21st century overhaul; and The Regal Beagle (named after the pub from "Three's Company") is a lively neighborhood bistro with a fabulous cocktail list—try a Reagle Peagle, made with gin, pea purée, mint and lime.
Things to Do
The John Fitzgerald Kennedy National Historic Site is an essential stop on anyone's trip to Boston: here the 35th President of the United States was born and raised. The Larz Anderson Auto Museum is the proud home to "America's Oldest Car Collection," housed in a building designed by Edmund M. Wheelwright who also designed the Boston Public Library. And cinephiles will love Coolidge Corner Theatre, a classic indie movie house showing all manner of thoughtfully programmed art-house wonders.