Few cities carry their history as proudly as Boston—or do as much with it. Start with the Freedom Trail and Boston Public Garden, then head to the Seaport, a former 18th-century shipping hub on the edge of South Boston that’s become one of the city’s most dynamic neighborhoods (sleek towers, seasonal open-air markets, and the Institute of Contemporary Art all anchor the waterfront). Then slow down in the South End, popping into art galleries, bookshops, and locally owned restaurants before catching live music at Wally’s Cafe Jazz Club.