11-Day Canada & New England Circle: Newfoundland & Montreal

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.

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.

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.

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.

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.

Old meets new in the province's capital (metro-area population a little more than 200,000), with modern office buildings surrounded by heritage shops and colorful row houses. St. John's mixes English and Irish influences, Victorian architecture and modern convenience, and traditional music and rock and roll into a heady brew. The arts scene is lively, but overall the city moves at a relaxed pace.For centuries, Newfoundland was the largest supplier of salt cod in the world, and St. John's Harbour was the center of the trade. As early as 1627, the merchants of Water Street—then known as the Lower Path—were doing a thriving business buying fish, selling goods, and supplying alcohol to soldiers and sailors.

By heading almost due east from Cap-aux-Meules in Canada, it is possible to reach France in about one day’s worth of steaming! With barely 6,000 inhabitants living on tiny St. Pierre, it is the smallest French Overseas Collective. The residents of St. Pierre are predominantly descendants of Normans, Basque and Bretons and the French spoken is closer to Metropolitan French than to Canadian French. Although Basque is not spoken any longer, the influence is still felt through sport and a Basque Festival. Interestingly, this small island has two museums in part dedicated to the Prohibition. The Musée Heritage is St. Pierre’s newest museum with a focus on medical artefacts from the 19th and 20th century. Another claim to fame is a guillotine, the only one ever used in North America. In this quirky village it is easy to find the Post Office; just look for the clock tower shaped like a praying monk.

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.