Kick-start your stay by visiting Boston must-sees such as Boston Common, Harvard University—the USA’s oldest—and the 1794-built USS Constitution tall ship docked at Charleston Navy Yard. To explore at your own pace, opt for a discount city sightseeing pass or hop-on hop-off trolley tour, or go with a guide on a walking, bike, or Segway tour. Next, focus on one of Boston’s claims to fame—its food—on a tour. Explore Little Italy and its pizzerias on a guided walk around the North End district, or take your taste buds around some of Boston’s famously good chocolate shops. In the evening, join a brewpub tour to discover some local craft beers before dinner at a gastropub. Or end the day on a creepy note with a ghost walking tour that delves into the city’s darkest corners and tales.

Devote today to a day trip—many of New England’s historical towns are within easy reach. Admire the gingerbread cottages and beaches of Martha’s Vineyard, or cast your net further along New England’s coast with a coach tour to places such as Kennebunkport and Cape Neddick Lighthouse. Another destination is Salem, the scene of notorious witch trials of 1692 and 1693. Group and private tours leave from Boston in the mornings and include visits to witch museums and cemeteries.

Trace the steps of America’s revolutionaries with a guided walk or drive along Boston’s Freedom Trail—a route studded with colonial-era buildings such as Paul Revere’s House. Perhaps combine it with a stroll around the elegant Beacon Hill and Copley Square neighborhoods; or discover Boston’s baseball heritage by exploring Fenway Park, one of the country’s oldest stadiums. Alternatively, see the wilder side of Boston on a seasonal whale-watching cruise—sailing to Massachusetts Bay to view the mammals in their natural habitat. Spend your last evening on a Boston harbor cruise. Typical options include cocktail cruises or boat trips with dinner and entertainment.