One of the country’s oldest cities, Boston played a fundamental role in U.S. history: Born of Puritan-colonist parents, the city came of age during the American Revolutionary War, lending both name and place to the Boston Massacre and Tea Party—back when the latter, ahem, was actually meaningful—and boasting such significant citizens as John and Samuel Adams, John Hancock, and Paul Revere. Yet the city has aged gracefully, so while history buffs can keep plenty busy here—and anyone could spend hours wandering gorgeous old neighborhoods like Beacon Hill—those seeking a younger, hipper Boston will not be disappointed.

Between meals, you might stroll the ribbon of public parkland known as the Rose Kennedy Greenway, introduced a few years ago with the long-overdue completion of the $15 billion Big Dig tunnel project. In Little Italy, you can pick up designer jeans and some of the best cannoli you’ll ever taste, while over in South Boston, contemporary art is blocks away from a nationally known craft-beer brewery. Crave seafood? Luckily, you’re on the coast and never far from a great lobster roll, be it from a trendy city oyster bar or a North Shore beach shack. Of course, you can’t leave Boston without some throwback treats: baked beans, Boston cream pie, a game at Fenway. In an old-school city like this, tradition is too wicked good to ignore.

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