New York City to Quebec City

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.

Like any seaport worth its salt, Saint John is a welcoming place but, more than that, it is fast transforming into a sophisticated urban destination worthy of the increasing number of cruise ships that dock at its revitalized waterfront. Such is the demand that a second cruise terminal opened in 2012, just two years after the first one, and 2013 will see the two-millionth cruise passenger disembark. All the comings and goings over the centuries have exposed Saint Johners to a wide variety of cultures and ideas, creating a characterful Maritime city with a vibrant artistic community. Visitors will discover rich and diverse cultural products in its urban core, including a plethora of art galleries and antiques shops in uptown.Industry and salt air have combined to give parts of Saint John a weather-beaten quality, but you'll also find lovingly restored 19th-century wooden and redbrick homes as well as modern office buildings, hotels, and shops.The natives welcomed the French explorers Samuel de Champlain and Sieur de Monts when they landed here on St. John the Baptist Day in 1604. Then, nearly two centuries later, in May 1783, 3,000 British Loyalists fleeing the aftermath of the American Revolutionary War poured off a fleet of ships to make a home amid the rocks and forests. Two years later the city of Saint John became the first in Canada to be incorporated.Although most of the Loyalists were English, there were some Irish among them. After the Napoleonic Wars in 1815, thousands more Irish workers found their way to Saint John. It was the Irish potato famine of 1845 to 1852, though, that spawned the largest influx of Irish immigrants, and today a 20-foot Celtic cross on Partridge Island at the entrance to St. John Harbour stands as a reminder of the hardships and suffering they endured. Their descendants make Saint John Canada's most Irish city, a fact that's celebrated in grand style each March with a weeklong St. Patrick's celebration.The St. John River, its Reversing Rapids, and Saint John Harbour divide the city into eastern and western districts. The historic downtown area (locally known as "uptown") is on the east side, where an ambitious urban-renewal program started in the early 1980s has transformed the downtown waterfront. Older properties have been converted into trendy restaurants and shops, while glittering new apartment and condo buildings will take full advantage of the spectacular view across the bay. Harbour Passage, a redbrick walking and cycling path with benches and lots of interpretive information, begins downtown at Market Square and winds along the waterfront all the way to the Reversing Rapids. A shuttle boat between Market Square and the falls means you have to walk only one way. On the lower west side, painted-wood homes with flat roofs—characteristic of Atlantic Canadian seaports—slope to the harbor. Industrial activity is prominent on the west side, which has stately older homes on huge lots.Regardless of the weather, Saint John is a delightful city to explore, as so many of its key downtown attractions are linked by enclosed overhead pedways known as the "Inside Connection."

Surrounded by natural treasures and glorious seascapes, Halifax is an attractive and vibrant hub with noteworthy historic and modern architecture, great dining and shopping, and a lively nightlife and festival scene. The old city manages to feel both hip and historic. Previous generations had the foresight to preserve the cultural and architectural integrity of the city, yet students from five local universities keep it lively and current. It's a perfect starting point to any tour of the Atlantic provinces, but even if you don't venture beyond its boundaries, you will get a real taste of the region.It was Halifax’s natural harbor—the second largest in the world after Sydney, Australia’s—that first drew the British here in 1749, and today most major sites are conveniently located either along it or on the Citadel-crowned hill overlooking it. That’s good news for visitors because this city actually covers quite a bit of ground.Since amalgamating with Dartmouth (directly across the harbor) and several suburbs in 1996, Halifax has been absorbed into the Halifax Regional Municipality, and the HRM, as it is known, has around 415,000 residents. That may not sound like a lot by U.S. standards, but it makes Nova Scotia’s capital the most significant Canadian urban center east of Montréal.There's easy access to the water, and despite being the focal point of a busy commercial port, Halifax Harbour doubles as a playground, with one of the world's longest downtown boardwalks. It's a place where container ships, commuter ferries, cruise ships, and tour boats compete for space, and where workaday tugs and fishing vessels tie up beside glitzy yachts. Like Halifax as a whole, the harbor represents a blend of the traditional and the contemporary.

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.

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.