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For a city that once seemed to suffer a serious inferiority complex at the hands of its New York neighbor to the south, Boston has, by all accounts, come into its own. No longer does the city find itself ranked second best – and why should it? Boston's cuisine is no longer a joke, its nightlife scene has finally burgeoned beyond college bars, and its beloved baseball team is cursed no more.

One of the most historically significant cities in the country, Boston is where the first plans for the American Revolution took shape, and where the country's first public park, first public library, and first subway were conceived. As home to more colleges and universities than any other city, however, this old city manages to remain perpetually young. The antiquated notion of the Boston Brahmin is almost extinct, and though you'll still find the buttoned-up set dining on gigantic cuts of beef inside the dark-wood paneled walls of the storied Oak Room (see Where to Eat), you'll see far more of the jet set sipping cocktails in the adjacent bar. Hip boutiques line centuries-old streets, the oldest watering hole in the country is dominated by 20-somethings wearing baseball hats and halter tops, and the Freedom Trail is used as often to reference the location of a bar as it is to direct someone to one of the 16 important historical sites found along its path. Spend a few days in Beantown, however, and you'll soon find that what's most appealing about Boston is not what has changed, but what has remained the same.

If you have three days, engage in an American history lesson along the red-brick Freedom Trail, head to the Italian North End for excellent food in a true ethnic neighborhood, take an afternoon to stroll Newbury Street and peruse its high-end clothing stores and art galleries, and wander the narrow, tree-lined streets of Beacon Hill. With five days, head over to Cambridge and explore the Harvard campus, do some people watching in the always-eclectic Harvard Square, and explore the city's waterfront by boat. A week will let you take in more of New England with a side trip – Cape Cod, the Berkshires, and the North Shore are all a short distance away. Friendly and manageable, the city is at once quaint and cosmopolitan, old and young, grand and diminutive. One piece of advice though: if you're a Yankees fan, you might want to keep it to yourself.

• Walking the red-brick Freedom Trail

• Sampling the vast array of food at Quincy Market

• Perusing the high-end shops on Newbury Street

• Strolling the tree-lined streets of Beacon Hill

• A ride on the swan boats in the Public Garden

• An Italian dinner in the North End

See Boston Travel Guide