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This Little Burgundy mainstay is the headquarters of chefs David McMillan and Frédéric Morin, the acclaimed and enterprising minds behind an evolving blackboard menu that has been known to feature smoked meat croquettes, house-cured ham with truffles, lobster spaghetti and horse meat steaks. The duo is known to do absolutely everything in-house, even brew their own beer and distil their own absinthe. Stroll down Rue Notre-Dame, past their other restaurant, Liverpool House, to the nearby Lachine Canal after an evening at this inviting space with vintage wooden chairs, leather banquettes and a permanent air of celebration.

On the still-bucolic site of a former coconut plantation just west of Montego Bay, Round Hill is another of the legendary hotels created in the early 1950s to accommodate wealthy Brits and Americans who were discovering the pleasures of a Jamaican winter. Since then, it has evolved into a thoroughly modern resort that manages to retain its original, exclusive, clublike spirit. In the beginning, Round Hill consisted of a group of shareholders (British playwright Noel Coward was one) who rented out their private villas when they were absent. That’s how it still works, although the celebrity shareholder most mentioned these days is designer Ralph Lauren, who rents neither of his two villas. Along with 27 other villas, which can be divided into 86 suites, there’s the Pineapple House, a seafront block of 36 rooms, all decorated, predominantly white on white, by Lauren. The ambience is quiet luxury, the service is relatively formal (the doorman wears white), and the children among the guests are treated as the heirs and future holiday decision makers that they are. Almost every villa has a story, whether it has to do with Coward, the Kennedys, or How Stella Got Her Groove Back. And Montego Bay, whose city lights can be seen only from the highest villa (#28), is still another world away.

A church—or, at least, a small chapel—has stood on the site of the Basilica of Notre-Dame since shortly after Ville-Marie (Montréal’s predecessor) was founded in 1642. The current building, however, dates to 1829 and was constructed in a soaring Gothic Revival style. At the time, that aesthetic choice raised some eyebrows—Gothic designs were associated more with Protestant churches than Roman Catholic ones. (Perhaps the fact that the architect was an Irish-American Protestant didn’t help the situation.) Whatever initial resistance there was evaporated in the face of the beauty of the completed building. In the decades that followed, Gothic became the popular choice for churches in Canada of every denomination in large part because of Montréal’s basilica. In the 1870s, in what was perhaps a case of gilding the lily, the basilica became even more stunning when its interiors were painted in bright colors to resemble Paris‘s Ste-Chapelle.

At 6,200 feet, Mont Ventoux—also known as the “Beast of Provence”—is the highest mountain in the Vaucluse region, and a popular part of the Tour de France cycling race. About half a mile from the summit stands a memorial to British cyclist Tom Simpson, who died during the 1967 Tour de France at just 29 years old. It serves as a sort of reminder to those tackling the grueling, 15.5-mile ascent, which, at some points, features a 10 percent gradient. At the top, winds can howl at up to 150 miles an hour, but the panoramic view stretches all the way from the Alps to the Mediterranean Sea. Despite being nicknamed the Bald Eagle, Mont Ventoux is a designated UNESCO Biosphere Reserve, with more than 1,000 species of flora and fauna. Take a drive to the top, then reward yourself with a visit to the Boyer nougat factory in nearby Sault, or a stop at the Vallon des Lavandes distillery on the Lavender Route.

Louise Loubatieres’ gorgeous light-filled little concept store on increasingly hip Hap Guan Street is one of those stores you can easily lose hours in. The fascinating shop is located in self-styled Kandal Village, a compact neighborhood of three parallel streets wedged between the French Quarter and Old Market area that has become an emerging shopping, eating and drinking district. The lovely Louise, who can often be found out the back of the shop baking or making a pot of tea, is of Cambodian, French, British, and Vietnamese heritage, and her ancestry is reflected in her impeccable taste and passion for arts, crafts, textiles and design objects from Southeast Asia, and her carefully curated selection of beautiful things. Unlike some of my favorite shops, Louise doesn’t limit herself to ‘made in Cambodia’ products, and won’t hesitate to source pretty things from places like Chiang Mai or the Mekong Delta if she discovers something special. Louise largely stocks homewares, from colorful lacquer bowls to textiles that can serve as table runners.

An overnight stay at Tonquin Valley Adventures’ lodge is perhaps the best way to experience the wilderness of the Canadian Rockies. (It’s a well-earned one, too: The lodge lies almost 20 kilometers, or about 12 miles, from the nearest road!) To get there, hike the Tonquin Valley backcountry from Edith Cavell Road to the path alongside Astoria River before reaching the Ramparts Mountains. The setting is surreal, as the lodge has a series of cabins with unforgettable views. A short walk leads guests to the edge of Amethyst Lake, where canoes, kayaks, and rowboats await to take you on your next adventure.

Since opening in 1819, Australia’s first barracks has housed British convicts, female immigrants, destitute elderly women, courtrooms, and government offices until it was finally declared a museum in 1979. During a twice-daily tour, or with the help of an audio guide, visitors get a glimpse of how high-skill prisoners lived, worked, and slept (on hammocks) during the 19th century—often freely working in the city by day but sleeping alongside more than 1,000 thieves, conspirators, bank robbers, pirates, and bushrangers by night. Offered in the original convict bakehouse and store, a house-made pot pie, burger, or cake with a schooner of beer at Bakehouse is a welcome end to the experience. Outside, freedom has never felt so good.

While many associate them with the British Isles, the Celts were the dominant culture in Switzerland for about a millennium (from around 500 B.C.E. to 400 C.E.). The country’s lakes, particularly Lake Neuchâtel, were the epicenter of Celtic culture here during the La Tène era, when Celtic settlements could be found from Turkey to Ireland. The Laténium Park and Archaeological Museum, named after extraordinary excavations in Neuchâtel, is home to the world’s premier collection of Celtic treasures unearthed in Europe. The museum boasts an übermodern design—by a consortium of four Geneva architects—that is impressive, but the hundreds of dazzling items that it houses are the real attraction: a Gallo-Roman ship, a Celtic bridge, and finely wrought gold, glass, and stone treasures found in and around the lakes. Ongoing exhibitions provide introductions to this culture that had a huge influence on the story of Europe. As the Laténium covers some 50,000 years of local history and not just the Celtic period, allow yourself a few hours to digest it all.

Fearing a British takeover of its ill-gotten trading post, the Dutch East India Company built this star-shaped castle (known as Kasteel de Goede Hoop) between 1666 and 1679 to defend its territory. Now the oldest building in South Africa, the castle served as the center of Cape Town‘s civilian, political, and military life. The austere facade opens up to a striking central lawn and commanding buildings that, in their restored form, represent Dutch, English, and French architectural styles. History buffs will go nuts here: Check out the William Fehr Collection, the African pottery exhibit, and the Castle Military Museum.

The Freedom Trail is the artery connecting most of Boston’s key Revolutionary War sites, from Boston Common to the USS Constitution—16 stops in all. Besides providing you with some history, following the red stripe around town also delivers an easy self-guided tour of the heart of Boston, including the lively North End and Charlestown. The Common, Old North Church, the Paul Revere House, and the site of the Boston Massacre are obvious and obligatory stops, but the trail also leads to three legendary cemeteries, the 1718 Old Corner Bookstore (now a Chipotle restaurant, of all things), the 1713 Old State House, and the unmissable Bunker Hill Monument, whose cornerstone was laid by Lafayette to mark the 50th anniversary of the bloody battle between British troops and patriot militias in June 1775.

A Montreal favorite, this wine bar is known for its elegant food and drinks— and comes recommended highly by Ritz-Carlton concierge Simon Bajouk. The wine selection is vast and the staff is extremely helpful in guiding visitors to something that they like. “Trios,” aka flights, are another good way to taste through a well curated selection. (Cocktails and local Quebecois beer are also available.) The food ranges from snacks like gougeres and nuts to porcini arancini and short ribs. A dish of green beens with truffle oil and almonds was fresh, light, and delicious; the charcuterie plate was a generous offering of various local salumi.

When Bouillon Bilk first opened in 2011, Montréal’s restaurant critics were intrigued. The chef, François Nadon, had worked at several of the city’s top restaurants but was largely unknown, and the restaurant was located on an undistinguished stretch of boulevard St-Laurent. But it soon became both a critical and popular favorite. The contemporary, minimal space is decidedly unstuffy compared with many of Montréal’s leading restaurants. Similarly, the menu may be gourmet but it’s also daring, with ingredients and preparations from Asia complementing French dishes and techniques. You can start with Japanese yellowtail, move on to a pasta dish, and end with a selection of Québecois cheeses, if you choose. There are also fresh oysters on the menu at both lunch and dinner.

The French chef Daniel Boulud made his name in New York, where he oversees seven restaurants and has since expanded his culinary empire to six other outposts around the globe. His venture in Montréal makes perfect sense, with Québecois cuisine combining French traditions and techniques with New World ingredients—not unlike Boulud himself. The space—by Super Potato, one of the hottest design firms today—is elegantly restrained, with smoked glass details, wooden floors, and a contemporary enclosed fireplace warming and lighting the room. Boulud uses the best of Québec’s produce in dishes centered on local foie gras, duck, and salmon. The result is refined yet soulful contemporary French dishes, prepared by Maison Boulud executive chef Riccardo Bertolino. In warmer months, guests can dine alfresco, while in the winter you can take in the snowy scene from the restaurant’s enclosed greenhouse. Image courtesy of Ritz-Carlton Montreal.

The province of Quebec is notorious for its quaint, picturesque villages. The compact forests and the thousands of lakes in the Laurentides region certainly make for the picture-perfect Canadian postcard, including the beautiful lakeside chapel in Saint-Alphonse or the wholesome locals of Old-Town Saint-Sauveur. On the other hand, the rolling hills of the Eastern Townships are as bucolic as it gets: villages like Hudson, with its gourmet market, microbrewery and century-old houses have a slight England feel, as does nearby Sutton. However, the ultimate wintery escape from Montreal surely is Quebec City, with the snow-capped Château Frontenac, 400+ year old historic center and festive winter Carnival every February.

To me, no other place in Montréal represents the city better than Place d’Armes. After all, it is the second oldest public site in the city, and its center is home to a statue of Paul de Chomedey, the founder of Montréal. And the varied architectural styles surround the square in a way that clearly demonstrates just how old and historic Montréal is. A blend of Gothic Revival, classic Art Deco, and ultra-modern sleek skyscrapers illustrates the major periods of Montréal’s development. It’s definitely a great place to start or end an Old Montreal exploratory tour, or to stop and people watch!