7-Day Canada & New England: Maine, Maritimes & 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.

Portland, Maine The largest city in Maine, Portland was founded in 1632 on the Casco Bay Peninsula. It quickly prospered through shipbuilding and the export of inland pines which made excellent masts. A long line of wooden wharves stretched along the seafront, with the merchants' houses on the hillside above. From the earliest days it was a cosmopolitan city. When the railroads came, the Canada Trunk Line had its terminal right on Portland's quayside, bringing the produce of Canada and the Great Plains one hundred miles closer to Europe than any other major U.S. port. Some of the wharves are now occupied by new condominium developments, with the exception of the Customs House Wharf, which remains much as it used to be. Grand Trunk Station was torn down in 1966 and a revitalization program of this historic section was spearheaded by a group of committed residents. The result was the revival of the Old Port Exchange District with its redbrick streets built in the 1860s following a disastrous fire. The area today features a wide variety of restaurants, specialty and antique shops, and makes for a pleasant place for a stroll. Congress Street and its many side streets are an engaging mixture of culture, commerce and history. Art is everywhere, from the Portland Museum of Art to the many statues and monuments throughout the city. Other points of interest include the Portland Observatory, Henry Wadsworth Longfellow's childhood home, several colonial mansions and Fort Williams Park, with the adjacent Portland Head Light. Farther afield one can visit the charming yachting and fishing village of Kennebunkport, also noted as the locale of the home and summer White House of former President George Bush. Going Ashore in Portland Pier Information The ship is scheduled to dock at the Portland Ocean Terminal, a very easy walk to the Old Port District located about two blocks away. Taxis are available at the pier. Shopping A wide range of Maine-made clothing, crafts and imported items can be found in shops along the cobblestone streets of the quaint Old Port Exchange. Small boutiques and numerous art galleries feature everything from paintings, crafts and furniture to prints and photographs. Antique lovers will enjoy browsing through area shops. Bargain hunters may want to visit the designer factory outlet shops in Freeport. On Sundays, most shops are open from 12:00 noon to 5:00-6:00 p.m. The local currency is the dollar. Cuisine Portland has the most restaurants per capita, second only to San Francisco. Eating establishments are as diverse as the menus they offer. The fresh catch of the day can be found on most menus, but seafood is only one of many culinary delights. From specialty coffee houses and ethnic restaurants to chowder and lobster houses to elegant dining rooms, Portland makes it easy to please every palate. Other Sights Longfellow's "City by the Sea" Portland is a walkable city, and a good place to start exploring is at the Old Port with its striking buildings comprising a bevy of architectural styles, ranging from Italianate to Mansard, Queen Anne to Greek Revival. The charming streets house an amazing collection of shops, galleries, bookstores and restaurants. Congress Street and the Arts District reflect the changes of 350 years of history, boasting an engaging mixture of culture and commerce. Portland Museum of Art The museum's award-winning building is a blend of 1911 Beaux Arts and 1983 post-modernism. It houses one of New England's finest art collections. Don't miss the museum's indoor Sculpture Garden. Portland Observatory Built in 1807, this is a rare example of a signal tower from which signal flags would be flown to identify incoming vessels. Factory Outlets of Freeport About a 25-minute drive north of Portland (approximately $35 one way for a taxi), this shopping mecca is crammed with serious shoppers who come from as far away as New York. Private arrangements for independent sightseeing may be requested through the Tour Office on board.

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.

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.