Transatlantic Crossing

From Wall Street's skyscrapers to the neon of Times Square to Central Park's leafy paths, New York City pulses with an irrepressible energy. History meets hipness in this global center of entertainment, fashion, media, and finance. World-class museums like MoMA and unforgettable icons like the Statue of Liberty beckon, but discovering the subtler strains of New York's vast ambition is equally rewarding: ethnic enclaves and shops, historic streets of dignified brownstones, and trendy bars and eateries all add to the urban buzz.

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.

If you come directly to Cape Breton via plane, ferry, or cruise ship, Sydney is where you’ll land. If you’re seeking anything resembling an urban experience, it’s also where you’ll want to stay: after all, this is the island’s sole city. Admittedly, it is not the booming center it was a century ago when the continent’s largest steel plant was located here (that era is evoked in Fall on Your Knees, an Oprah Book Club pick penned by Cape Bretoner Anne-Marie MacDonald). However, Sydney has a revitalized waterfront and smattering of Loyalist-era buildings that appeal to visitors. Moreover, it offers convenient access to popular attractions in the region—like the Miner’s Museum in nearby Glace Bay (named for the glace, or ice, that filled its harbor in winter), the Fortress at Louisbourg, and beautiful Bras d'Or Lake.

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.

Québec City's alluring setting atop Cape Diamond (Cap Diamant) evokes a past of high adventure, military history, and exploration. This French-speaking capital city is the only walled city north of Mexico. Visitors come for the delicious and inventive cuisine, the remarkable historical continuity, and to share in the seasonal exuberance of the largest Francophone population outside France.The historic heart of this community is the Old City (Vieux-Québec), comprising the part of Upper Town (Haute-Ville) surrounded by walls and Lower Town (Basse-Ville), which spreads out at the base of the hill from Place Royale. Many sets of staircases and the popular funicular link the top of the hill with the bottom. Cobblestone streets, horse-drawn carriages, and elaborate cathedrals here are charming in all seasons. The Old City earned recognition as an official UNESCO World Heritage site in 1985, thanks largely to city planners who managed to update and preserve the 400-year-old buildings and attractions without destroying what made them worth preserving. The most familiar icon of the city, Fairmont Château Frontenac, is set on the highest point in Upper Town, where it holds court over the entire city.Sitting proudly above the confluence of the St. Lawrence and St. Charles rivers, the city's famous military fortification, La Citadelle, built in the early 19th century, remains the largest of its kind in North America. In summer, visitors should try to catch the Changing of the Guard, held every morning at 10 am; you can get much closer to the guards here than at Buckingham Palace in London.Enchanting as it is, the Old City is just a small part of the true Québec City experience. Think outside the walls and explore St-Roch, a downtown hot spot, which has artsy galleries, foodie haunts, and a bustling square. Cruise the Grande-Allée and avenue Cartier to find a livelier part of town dotted with nightclubs and fun eateries. Or while away the hours in St-Jean-Baptiste, a neighborhood with trendy shops and hipster hangouts.