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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.

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!

Each summer the Atlantic Film Festival brings Halifax the AlFresco FilmFesto on the waterfront boardwalk. The AlFresco FilmFesto takes place on Friday nights from July to August and features outdoor movies, often with a theme, like Billy Murray movies or Spielberg films. They are projected on a large screen on the boardwalk which runs along the harbor. It’s free (with a requested donation), so bring a blanket or chair to sit on and enjoy a movie under the stars.

There is something fundamentally different in the air of this Eastern Townships winery—something I couldn’t quite grasp but that made me want to stay forever. The winery, which specializes in ice wines and ciders, was founded a few years ago by three young, passionate investors and lifelong friends, and it has since received immense praise, both from its clientele and the wine industry. For me, I think the setting is what sets it apart from other wineries. A charming bright-red barn overlooks acres of dense forest and rolling hills.

The little town of Baie-St.-Paul has been a haven along the north shore of the St. Lawrence since the 1670’s, when the French began settling here. Today, just a couple of hours from Québec city by car, it’s an artist’s colony full of charming galleries and restaurants. I hadn’t been here in over a decade when I brought my wife here for her first visit. The dramatic Charlevoix region (the rolling landscape northeast of Québec city) was one of her favorite areas, and we spent an afternoon here, reveling in the cool green, soaking up the contrast from home in Arizona...

In a remote spot off Vancouver Island in British Columbia, surrounded by rain forest, mountains, and beaches, the Clayoquot Wilderness Retreat first opened in 1998 as an overnight floating lodge experience; since then, it has grown into a luxury tent retreat. While the camp has a rugged outpost atmosphere, with huge stone fireplaces and a long wooden cookhouse, it’s an outpost with every possible luxury: from white linen tablecloths and polished silverware to soft comforters and high-thread-count bedding.

This busy restaurant sits on Rue Saint-Paul, a street in Lower Town that’s lined with antique shops, hence the name. Buffet de L’Antiquaire is a classic diner—but with a Québecois twist—that has been a mainstay of the city’s dining scene for more than 40 years. The reasonably priced menu lists traditional dishes like boudin (blood sausage) and pork stew among the entrées and sugar pie and crepes among the desserts. (You can also order more typical diner fare, from burgers to omelettes.) It is open early to late, from 6 a.m. to 10 p.m. seven days a week, adding to its popularity.

Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.

You can find a respectable beer selection at most Banff Avenue restaurants, but a well-crafted cocktail requires a little more intel. For a fabulous mixed drink, head to Block Kitchen + Bar on Caribou Street, an intimate venue specializing in all things shaken and stirred. With concoctions like the Gin Beetroot Sour and the Coffee & Artichoke Negroni, you’ll be glad you ventured off the main drag. You can grab tapas and gourmet sandwiches here too, like the Red Devil Calamari appetizer with spicy Thai sauce or the Kuterra Salmon on ciabatta bread. Keep in mind this teeny spot has limited seating, so arrive early or roll in fashionably late to get a seat.

Handily situated two minutes from the subway, and at the junction of three of the city’s most popular tourist neighborhoods, the Hotel Place d’Armes makes for an easy, car-free vacation. Situated in a beautifully restored stone building with intricate gargoyles, pillars, and oversize arcade widows dating back to 1870, it was originally the Great Scottish Life Insurance Company building. The rather masculine formal lobby gives way to plenty of cozy nooks and inviting couches, with a pool table on offer for those who fancy a game. Guest rooms feature original, exposed brick and stone walls, and the earthy natural palette is brightened by deep-red leather chairs and couches. The Place d’Armes has an easy upgrade policy, so it’s worth asking for one upon check-in; most guests will get an upgrade on request, depending on availability. Throughout summer, the hotel’s rooftop Terrasse is one of the city’s most popular outdoor hot spots.

The atmosphere alone in this Iranian restaurant is a wonderful introduction to any day. The sunny, high-ceilinged space on Avenue Laurier Ouest is decorated with nice wooden furniture and traditional Middle-Eastern patterned pillows, for your ultimate comfort as you sip sweet mint tea served in small gilded glasses and decide what to order. Will it be the selection of flatbreads served with fresh herbs, nuts and fresh cheese? It comes with a selection of house-made jams like kiwi and passion fruit or orange blossom. The “omelets” are also very special – they’re actually scrambled eggs mixed with ingredients such as feta cheese and dill. Photo: Frédérique Ménard Aubin

Not unlike the Eiffel Tower in Paris or the Empire State Building in NYC, the Mont Royal acts as a natural landmark for orientation-challenged travelers. The “mountain” (some would call it a big hill) overlooks the entire city and offers unparalleled panoramas of downtown and the Eastern Townships south of the city. The entire mountain is actually a city park, with many things to do besides admiring the view: tam-tam jams, bird watching, cycling, forest treks—and even skiing, snowshoeing, ice skating, and sledding in the winter. Brownie points if you make it to the Kodiaronk lookout at dawn, in time to see the sun rise behind the skyscrapers.

This place is nothing short of a local institution. Bo-Bec has served countless cones and ice cream sandwiches since it opened in the late 1980s, but the owner never changed the warm, genuine smile he offers every customer who walks in. And that makes all the difference. Bo-Bec doesn’t serve just any ice cream. Everything is handmade, and about half of the flavors available at the counter are original concoctions, be it maple nougat or rose water strawberry. They even have vegan ice cream! The perfect spot for a post-dinner treat or to take away and eat in the massive park around the corner.

The Carré Saint-Louis (also known as St. Louis Square) is one of Montréal’s most important literary streetscapes. Famed Québecois poets Émile Nelligan and Gaston Miron called this home. Brightly painted Victorian/Second Empire graystone rowhouses line the square—one of the best leafy spaces in the city. (It’s been called “the closest thing to a European neighborhood square you’ll find this side of the Atlantic” by the Project for Public Spaces.) A few blocks away is the fabled Schwartz’s Deli. Grab a “smoked meat” to go, then come here to chow down by the fountain, surrounded by trees and 19th-century façades. (The nearest subway is Sherbrooke station on the Orange Line.)

Marble footpaths meander up pine-clad Filopappou Hill, a peaceful hideout for picnickers and joggers. Hidden in a rocky clearing is the Pnyx, the world’s first democratic assembly, where the great orators Pericles and Themistocles held court in the 5th century B.C.E. The Pnyx could hold 18,000 citizens on wooden benches, with standing room for thousands more. Imagine the scene when the founding fathers of democracy took to the podium—and enjoy the phenomenal cityscape from this historic vantage point, with the Acropolis in the foreground. Climb all the way to the summit of Filopappou (also known as the Hill of the Muses) and you can see all the way to the port of Piraeus, with the promise of nearby islands shimmering on the horizon. Crowning the adjacent Hill of the Nymphs, the National Observatory is Greece’s oldest research institute. Set in lovely landscaped gardens, the charming 19th century building contains rare books and antique astronomical equipment. Occasional evening tours offer the chance to stargaze through a refracting telescope and learn about the Greek myths written into the constellations.