Day 1 Montréal, Québec, Canada

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.

Day 2 Quebec City, Québec, Canada

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.

Day 3 Saguenay, Québec, Canada

Just after visiting Saguenay, the wonderful Saguenay River pours into the massive St. Lawrence River. Before then, however, it slices through one of the world's most southerly fjords and dense forests of towering pine trees. The nature watching here is nothing short of sublime, with outdoor spots like the Parc National du Fjord-du-Saguenay offering panoramic vistas and sandy river-beaches. Island-sized blue whales cruise through the waters of the mighty rivers, and flick gallons of water into the air effortlessly with a single swish of their colossal tails. With hiking, kayaking and cycling opportunities inviting you to explore the spectacular scenery - you'll find endless ways to fall in love with this majestic outdoor escape. In fall, gorgeous colours ripple through the foliage, and in doing so, they provide one of nature's greatest performances.

Day 4 Baie Comeau, Québec, Canada

Day 5 Havre-Saint-Pierre, Québec, Canada

Havre St. Pierre is a tiny seaside port on the north shore of the Saint Lawrence River in Quebec. It was settled in 1857 by Acadians from the Magdalen Island, and still today locals speak a dialect more similar to Acadian French than to Quebec French. It was originally called Saint-Pierre-de-la-Pointe-aux-Esquimaux until 1927, when it was officially shortened to Havre St Pierre. Until recently the local economy relied mainly on fishing and lumbering, today it is mainly a titanium ore-transhipment port. Nearby is one of the world's most amazing natural phenomena – the Mingan Archipelago. They are the largest group of erosional monoliths in Canada, and were declared a Nation Park in 1984. These limestone monoliths have formed over thousands of years by wave action, strong winds and seasonal freezing and thawing. The result is a unique set of large limestone sculptures.

Day 7 Corner Brook, Newfoundland and Labrador, Canada

Newfoundland's fourth-largest city, Corner Brook is the hub of the island's west coast. Hills fringe three sides of the city, which has dramatic views of the harbor and the Bay of Islands. The town is also home to a large paper mill and a branch of Memorial University. Captain James Cook, the British explorer, charted the coast in the 1760s, and a memorial to him overlooks the bay.The town enjoys more clearly defined seasons than most of the rest of the island, and in summer it has many pretty gardens. The nearby Humber River is the best-known salmon river in the province, and there are many kilometers of well-maintained walking trails in the community.

Day 8 Sydney, Nova Scotia, Canada

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.

Day 9 Halifax, Nova Scotia, Canada

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.

Day 10 Saint-John, New Brunswick, Canada

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."

Day 11 Portland, Maine, United States

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.

Day 13 New York, New York, United States

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.

Day 17 Tortola, British Virgin Islands

The bustling capital of the BVI looks out over Road Harbour. It takes only an hour or so to stroll down Main Street and along the waterfront, checking out the traditional West Indian buildings painted in pastel colors and with corrugated-tin roofs, bright shutters, and delicate fretwork trim. For sightseeing brochures and the latest information on everything from taxi rates to ferry schedules, stop in at the BVI Tourist Board office. Or just choose a seat on one of the benches in Sir Olva Georges Square, on Waterfront Drive, and watch the people come and go from the ferry dock and customs office across the street.

Day 18 Saint John's, Antigua and Barbuda

With its superb beaches, historical attractions and beautiful coral reefs, Antigua provides a host of diversions. It is said that the island contains 365 beaches, one for every day of the year. Antigua maintains its traditional West Indian character, with gingerbread-house style architecture, calypso music and carnival festivities. St John's has been the administrative capital since the island's colonisation in 1632, and has been the seat of government since it gained independence in 1981. From the port you can explore the colourful Redcliffe district, with its restored wooden houses, and Heritage Quay with its shopping mall and craft shops. The city has some fine examples of Colonial architecture, including the twin-towered cathedral, built in 1845 and considered one of the finest church buildings in the Caribbean. All coaches in Antigua are operated by smaller vehicles, and commentary will be given by a driver/guide.

Day 19 Basseterre, Saint Kitts, Saint Kitts and Nevis

Mountainous St. Kitts, the first English settlement in the Leeward Islands, crams some stunning scenery into its 65 square miles (168 square km). Vast, brilliant green fields of sugarcane (the former cash crop, now slowly being replanted) run to the shore. The fertile, lush island has some fascinating natural and historical attractions: a rain forest replete with waterfalls, thick vines, and secret trails; a central mountain range dominated by the 3,792-foot Mt. Liamuiga, whose crater has long been dormant; and Brimstone Hill, known in the 18th century as the Gibraltar of the West Indies. St. Kitts and Nevis, along with Anguilla, achieved self-government as an associated state of Great Britain in 1967. In 1983 St. Kitts and Nevis became an independent nation. English with a strong West Indian lilt is spoken here. People are friendly but shy; always ask before you take photographs. Also, be sure to wear wraps or shorts over beach attire when you're in public places.

Day 21 Kralendijk, Bonaire

Day 22 Willemstad, Curaçao

Dutch settlers came here in the 1630s, about the same time they sailed through the Verazzano Narrows to Manhattan, bringing with them original red-tile roofs, first used on the trade ships as ballast and later incorporated into the architecture of Willemstad. Much of the original colonial structures remain, but this historic city is constantly reinventing itself and the government monument foundation is always busy restoring buildings in one urban neighborhood or another. The salty air causes what is called "wall cancer" which causes the ancient abodes to continually crumble over time. The city is cut in two by Santa Anna Bay. On one side is Punda (the point)—crammed with shops, restaurants, monuments, and markets and a new museum retracing its colorful history. And on the other side is Otrobanda (literally meaning the "other side"), with lots of narrow, winding streets and alleyways (called "steekjes" in Dutch), full of private homes notable for their picturesque gables and Dutch-influenced designs. In recent years the ongoing regeneration of Otrobanda has been apparent, marked by a surge in development of new hotels, restaurants, and shops; the rebirth, concentrated near the waterfront, was spearheaded by the creation of the elaborate Kura Hulanda complex.There are three ways to cross the bay: by car over the Juliana Bridge; by foot over the Queen Emma pontoon bridge (locally called "The Swinging Old Lady"); or by free ferry, which runs when the pontoon bridge is swung open for passing ships. All the major hotels outside town offer free shuttle service to town once or twice daily. Shuttles coming from the Otrobanda side leave you at Riffort. From here it's a short walk north to the foot of the pontoon bridge. Shuttles coming from the Punda side leave you near the main entrance to Ft. Amsterdam.

Day 23 Oranjestad, Aruba

Aruba's capital is easily explored on foot. Its palm-lined central thoroughfare runs between old and new pastel-painted buildings of typical Dutch design (Spanish influence is also evident in some of the architecture). There are a lot of malls with boutiques and shops—the Renaissance mall carries high-end luxury items and designer fashions. A massive renovation in downtown has given Main Street (a.k.a. Caya G. F. Betico Croes) behind the Renaissance Resort a whole new lease on life: boutique malls, shops, and restaurants have opened next to well-loved family-run businesses. The pedestrian-only walkway and resting areas have unclogged the street, and the new eco-trolley is free and a great way to get around. At this writing, Linear Park was well and will showcase local merchants and artists. There will be activities along a boardwalk that will eventually run all the way to the end of Palm Beach, making it the longest of its kind in the Caribbean.

Day 25 Ocho Rios, Jamaica

Day 26 Georgetown, Grand Cayman, Cayman Islands

Begin exploring the capital by strolling along the waterfront Harbour Drive to Elmslie Memorial United Church, named after the first Presbyterian missionary to serve in Cayman. Its vaulted ceiling, wooden arches, and sedate nave reflect the religious nature of island residents. In front of the court building, in the center of town, names of influential Caymanians are inscribed on the Wall of History, which commemorates the islands' quincentennial in 2003. Across the street is the Cayman Islands Legislative Assembly Building, next door to the 1919 Peace Memorial Building. In the middle of the financial district is the General Post Office, built in 1939. Let the kids pet the big blue iguana statues.

Day 28 Miami, Florida, United States

Miami is one of the world's most popular holiday spots. It has so much to offer; from its countless beach areas, to culture and museums, from spa and shopping days out, to endless cuban restaurants and cafes. Miami is a multicultural city that has something to offer to everyone.