Boston to Montreal

There’s history and culture around every bend in Boston—skyscrapers nestle next to historic hotels while modern marketplaces line the antique cobblestone streets. But to Bostonians, living in a city that blends yesterday and today is just another day in beloved Beantown.

Halifax exudes a fine European air and lies along the edge of the Atlantic Ocean. Visitors by sea are greeted by the 1758 Sambro Island Lighthouse, the oldest surviving beacon in North America. In the harborside Historic Properties district, grand and charming stone buildings built in the 18th and 19th centuries grace the cobblestone streets. The city grew up around Citadel Hill, where Fort George protected the harbor. The fortress, along with the adjacent stately Halifax Town Clock, has been gloriously restored and preserved.

The largest city on Cape Breton Island, Sydney is located along the southeastern arm of Sydney Harbour, at the mouth of its eponymous river. Founded in 1785 by the British and loyalists fleeing from the US following the American Revolution, Sydney was the capital of the island until 1820, when the colony of Cape Breton merged with Nova Scotia. The region’s coal mines drew many immigrants during the 19th century; by the early 20th century, Sydney had also become one of the world’s largest steel producing centers. Today, it is Nova Scotia’s second largest industrial complex.

Designated as the Island capital in 1765, Charlottetown is both PEI’s oldest and largest urban center. However, since the whole "metropolitan" area only has a population of about 65,000, a pleasing small-town atmosphere remains. The city is a winner appearance-wise as well. Peppered with gingerbread-clad homes, converted warehouses, striking churches, and monumental government buildings, Charlottetown’s core seems relatively unchanged from its 19th-century heyday when it hosted the conference that led to the formation of Canada. The city is understandably proud of its role as the "Birthplace of Confederation" and, in summer, downtown streets are dotted with people dressed as personages from the past who’ll regale you with tales about the Confederation debate.

Quebec City is by many accounts the most French city in New France. The Old Town’s centerpiece, the magnificent Château Frontenac, seems transported from the palatial landscapes of the Loire Valley, and its French-accented streets lead past white-stone buildings that evoke old-world medieval villages. The only remaining walled city in North America outside of Mexico, Quebec City was fortified in the 17th century soon after its founding in 1608. Its strategic setting on the rocky promontory of Cape Diamond gave troops a close view of the St. Lawrence.

Canada's most diverse metropolis, Montréal, is an island city that favors style and elegance over order or even prosperity, a city where past and present intrude on each other daily. In some ways it resembles Vienna—well past its peak of power and glory, perhaps, yet still vibrant and grand.But don't get the wrong idea. Montréal has always had a bit of an edge. During Prohibition, thirsty Americans headed north to the city on the St. Lawrence for booze, music, and a good time, and people still come for the same things. Summer festivals celebrate everything from comedy and French music and culture to beer and fireworks, and, of course, jazz. And on those rare weeks when there isn't a planned event, the party continues. Clubs and sidewalk cafés are abuzz from late afternoon to the early hours of the morning. And Montréal is a city that knows how to mix it up even when it's 20 below zero. Rue St-Denis is almost as lively on a Saturday night in January as it is in July, and the festival Montréal en Lumière, or Montréal Highlights, enlivens the dreary days of February with concerts, balls, and fine food.Montréal takes its name from Parc du Mont-Royal, a stubby plug of tree-covered igneous rock that rises 764 feet above the surrounding cityscape. Although its height is unimpressive, "the Mountain" forms one of Canada's finest urban parks, and views from the Chalet du Mont-Royal atop the hill provide an excellent orientation to the city's layout and major landmarks.Old Montréal is home to museums, the municipal government, and the magnificent Basilique Notre-Dame-de-Montréal within its network of narrow, cobblestone streets. Although Montréal's centre-ville, or Downtown, bustles like many other major cities on the surface, it's active below street level as well, in the so-called Underground City–-the underground levels of shopping malls and food courts connected by pedestrian tunnels and the city's subway system, or métro. Residential Plateau Mont-Royal and trendy neighborhoods are abuzz with restaurants, nightclubs, art galleries, and cafés. The greener areas of town are composed of the Parc du Mont-Royal and the Jardin Botanique.