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Quebec

Quebec City looks, at first glance, much like one of France's Atlantic coastal cities. A UNESCO-designated World Heritage site, Quebec City has gabled buildings dating from the 1600s and narrow, winding streets made of cobblestones. You can amble through airy plazas—past fountains and statues—as you make your way to Terrasse Dufferin, a wide promenade straddling the clifftop with fantastic views of the St. Lawrence River below. Presiding over it all is the Chateau Frontenac, a grand hotel reminiscent of a French castle. Stone fortifications, built by the French and improved upon by the British, circle the old center of Vieux Quebec and set it apart from any other city in Canada or the U.S. The walls divide Basse Ville (lower town) from Haute Ville (upper town), and are a testament to military conflicts involving the Iroquois, French, English and Americans. Beyond its deep history, Quebec City offers other enticements: The city's culture revolves around wining, dining and dancing (and more wining and dining). You will eat and drink well there. Cultural events by the likes of Cirque du Soleil, music festivals with free performances, and caleche horse-and-carriage rides take over the city in the warm-weather months. The capital of the province of Quebec, Quebec City has a bon-vivant temperament that sets it apart from Canada's English-speaking cities. Which leads us to the language question. Almost all Quebec City residents speak French as their primary tongue, but most who work in the tourist areas also speak some English—and they are friendly and helpful to visitors.

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Charlottetown

Charlottetown likes to relive its pivotal role in history—the birthplace of unified Canada. Today, it's also one of the tourism hubs of Prince Edward Island, where visitors can spend time shopping and eating after they've seen the historic sites or toured the island.

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Sydney

As alluring as Nova Scotia's scenic routes are, you might also consider visiting Cape Breton Island's only city. Along with a boardwalk-edged waterfront, Sydney has numerous historic buildings, including Cossit House Museum. Believed to be the oldest residence in the city, it was erected by the town's first Anglican minister, Ranna Cossit, in 1787. Other heritage buildings are St. George's Church (where Cossit preached); St. Patrick's Church (the island's oldest Roman Catholic church); and Jost House (a 1700s home containing exhibits and special collections). Note that Sydney also makes a good base for touring, as it offers easy access to less-developed neighboring communities on the so-called Marconi Trail, such as Sydney Mines (on the north side of Sydney Harbour) and Glace Bay (11 mi/18 km northeast). The former is home to the small but interesting Heritage Museum and Fossil Centre. The latter is where you'll find the Marconi National Historic Site: Dedicated to the Italian radio pioneer, it has a replica of the wireless station that broadcast the first transatlantic message to Europe at the turn of the 20th century. Another Glace Bay highlight is the Cape Breton Miners' Museum. Be sure to take the tour: After you're issued a hard hat and a protective cape, a retired miner leads you down to a damp, cramped mine typical of the 1930s. As an added bonus, the Marconi Trail's marquee site, Fortress of Louisbourg, is only 18 mi/28 km southeast of Sydney, and Baddeck is 50 mi/81 km west.

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Halifax

Throughout its history, Halifax, Nova Scotia, has been defined by the Atlantic Ocean. Its blue-gray presence is visible from the city's glass high-rises, centuries-old buildings and surrounding hills. Being built around a huge natural harbor that's second size-wise only to the one in Sydney, Australia, Halifax boasts a vibrant port that has catered to both commercial and naval vessels for more than 260 years. The fact that it was recently awarded a Can$25-billion federal shipbuilding contract further underscores how Halifax's ocean access drives the provincial economy. That same body of water also makes it an ideal tourist destination. The water offers ample recreational opportunities, and most major attractions—from the Maritime Museum of the Atlantic and the Canadian Museum of Immigration at Pier 21 to the Halifax Citadel (which was originally built to defend against sea attacks)—reflect the role it has played in the city's evolution. Whether you are strolling on the photogenic 0.6 mi/1 km harbourfront boardwalk, which extends from Casino Nova Scotia to Marginal Road, or hiking in Point Pleasant Park and Sir Sandford Fleming Park, which face each other across the Northwest Arm, water is virtually everywhere—and foodies will marvel at the fresh seafood it yields. Nevertheless, there is more to Halifax than the ocean. As the capital of Nova Scotia and the largest Canadian city east of Quebec, Halifax is a center for government, business and health care, which translates into a relatively affluent population. It is a center for higher education, too, with students from six universities injecting a decidedly youthful energy. When you combine those two demographics and factor in locals' famously friendly nature, it is easy to see why Halifax is also an entertainment hotspot, complete with a thriving arts community, an active music scene and nightlife options that few cities of its size can rival.

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Portland, ME

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.

Boston

Boston

Boston, Massachusetts, is inundated with visitors every year and for good reason: It's partly a walkable historic park (especially the Freedom Trail) and partly a modern waterfront metropolis (the "Hub of New England") with no lack of things to do once darkness descends. Fenway Park—one of the nation's most hallowed baseball stadiums—is a destination in itself. Although the city has never stopped reaching for the future and now welcomes leading-edge financial services and tech companies, it has lovingly preserved the treasures of its past. Boston cherishes its patriotic connections with the Boston Tea Party and Bunker Hill. It is a living symbol of the melting pot early residents fought to create, including lively ethnic neighborhoods, sophisticated centers of academia and sedate sanctuaries of old wealth. Each seems a world unto itself, yet each is an integral part of Boston's urban identity. Even with so much to do and so many doing it, the city is a relatively easy place to visit. Boston's attractions and historical sites are laid out in simple-to-follow walking tours, and its subway system efficiently whisks passengers around the city. You won't need a car, which is good: Driving in Boston is hair-raising, even for locals. The most difficult part of your visit may be opening your credit-card bill after you get home: Boston can be expensive, but you'll find a lot to enjoy for each dollar spent.

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