After you land at Montréal, you'll be transferred to the Ritz-Carlton Montréal, your home for the next two nights. It's located on the city's Golden Square Mile, where Montreal’s elite built their mansions. Just down the street, the Montreal Museum of Fine Arts is located in four different buildings, with its permanent collection and temporary exhibits covering the best of Canadian and international art. For shoppers, the Montreal location of Holt Renfrew, Canada's upscale department store, may prove to be a distraction. Even if you aren't shopping for designer duds, the neighborhood has some good lunch options including Alexandre et Fils and Anton & James Urban Cafeteria. In the afternoon, wander the streets of Old Montréal, with its oldest buildings dating from the 17th century. The Place Jacques-Cartier, the Notre-Dame Basilica of Montréal, and the Château Ramezay are just a few of the must-see sites in this atmospheric neighborhood. Tonight you’ll dine at H4C Place St-Henri, located in a former post office a block from the Notre-Dame Basilica. Chef Dany Bolduc has earned a loyal following with his innovative dishes—his signature foie gras dumplings are not to be missed.

On your second day, skip from historic Montréal to some of its modernist masterpieces. The Olympic Park, constructed for the 1976 Games, is still used for occasional sporting events while the velodrome now houses the city’s Biodôme, a unique series of four different environments from arctic to temperate rainforests with more than 4,000 animals and 500 plant species. Travelers with a green thumb will want to stop by the nearby Botanical Garden, one of the largest botanical gardens in the world, home to 22,000 plant species and cultivars, 10 exhibition greenhouses and more than 30 thematic gardens. Head next to the Plateau Mont-Royal neighborhood where boutiques and restaurants occupy the Victorian-era buildings. From the bistro fare at L’Express to smoked meats at Schwartz’s, Cari will provide personalized lunch recommendations. In the afternoon, dive deeper into the city’s cultural highlights at institutions like the McCord Museum, a social history museum that celebrates Montreal’s people with engaging exhibitions, and the Musée d’art contemporaine de Montréal. Or head instead to the beautiful Mount Royal Park, laid out in part by Frederick Law Olmsted. Montreal is a haven not just for fine arts but the performing arts as well, with more than 100 festivals year-round, and Cari will arrange for tickets to a musical or theatrical performance, preceded by an early dinner at Brasserie T! Located in the Quartier des Spectacles, it’s the more casual alternative from one of the city’s top restaurateurs, Normand Laprise of Toque!

After breakfast, head outside Montréal to the Eastern Townships. From the city, it's only an hour and a half drive up to picturesque Lake Massawippi. Your base for exploring the area will be the Manoir Hovey, an inn which was built as a home in 1900 and is loosely based on the design for Mount Vernon. The inspiration is perhaps appropriate, given that Lake Massawippi was a popular summer destination with Americans, and especially Southerners. Today, the rooms at the Relais & Chateaux property are a mix of traditional and contemporary, while the restaurant has become a destination in its own right with its creative cuisine and lakefront setting. There are a number of other country inns in a range of budgets and styles that you can choose from instead of the Manoir Hovey for your customized itinerary.

After a morning breakfast at your hotel, you’ll explore the town of North Hatley, population 750, on the shores of Lake Massawippi. The town was founded by Loyalists who left New England following the American Revolution and its long history is waiting to be uncovered by curious travelers. Afterwards you’ll transfer 50 minutes to the village of Sutton for a coffee and a stroll. From there you’ll depart on two wheels, riding on quiet country roads to the Abbaye de Saint-Benoit-du-Lac, founded in 1912. You might be able to hear the monks and their Gregorian chants while picking up some cheese and applesauce in the shop.

On the morning of your fifth day, rise early and ride south on rolling country roads, stopping at various picturesque towns along the way. At Beebe, on the US-Canadian border, stop for lunch at an iconic creperie like Le Tomifobia, which serves dishes straight from Brittany. Many towns in Eastern Townships region straddle the border, with only one step separating the two countries. In fact, when you visit the Stanstead Opera House, note that the audience sits on American soil while the stage is in Canada. After lunch, transfer back to Montreal for your return flight home.