7-Day Canada & New England Circle: New Brunswick

Squint your eyes and admit it: Doesn’t that skinny, bearded hipster walking down the cobbled street look a lot like a 19th-century sea captain heading to the wharf to check his ship? Modern Portland, first settled in 1633, carries the marks of both subsets of Mainers. The restored brick buildings and warehouses of the Old Port and the fine upright houses of prosperous captains, merchants and shipbuilders make the city’s past a living part of its present. And the waterfront is a going concern, not a museum: Fishing boats chug into and out of their berths, buoys clang, harbor seals bark. Those shop windows aren’t displaying hardtack, rope or hand salve, though. Juice joints, art galleries, bookstores (and comic-book stores!), worshipful temples to coffee, locavore bistros with national press, bespoke menswear designers and gelato shops all jostle for attention. Don’t limit your visit to the Old Port, though. Wander through the terrific art museum or take a tour of one of the city’s historic homes. Jump on a ferry or whale-watching boat and get out into the busy harbor. Head to the coast—craggy, windswept, dramatic—a glorious and undeniably New England panorama. Get out and take it all in. Welcome to Vacationland.

New England’s largest city, Boston, Massachusetts, is home to historic sights and modern neighborhoods; stores and restaurants with old-time character; and gracious green spaces as well as a beautiful waterfront. Legendary figures of the American Revolution come alive at buildings and attractions along Boston’s Freedom Trail, including the Paul Revere House and Old South Meeting House, and in Lexington and Concord just outside Boston. Pay homage to great U.S. presidents at the John F. Kennedy Presidential Library and Museum and in the town of Quincy, birthplace of Presidents John Adams and John Quincy Adams. Each of Boston’s neighborhoods has its own personality and things to do, whether you’re enjoying the food of the North End’s Little Italy, admiring the beautiful 19th-century architecture of Beacon Hill or watching the street performers in Cambridge’s Harvard Square. The waterfront offers harbor views, while boat tours allow you to take in the city skyline while sightseeing. In every neighborhood, shopping and dining reveal Boston’s true eclectic self, from casual to high-end, but always interesting. Finally, Boston is a city of green spaces where you can relax and enjoy the outdoors. The Emerald Necklace, designed by Frederick Law Olmsted, is a 445-hectare (1,100-acre) chain of nine linked parks, including the lovely Boston Common and Public Garden.