After lunch, head north to Jean-Talon Market, one of Montréal’s great public markets. It’s a feast of Québec cheeses, seasonal produce and maple treats. As the afternoon unfolds, head south toward Griffintown, where former industrial warehouses have been converted into modern art galleries, craft breweries and stylish cafés along the historic Lachine Canal. Rent a cruiser for a ride along the waterfront before continuing east into Old Montréal, where the modern streets give way to centuries-old stone facades, cobblestone laneways and public plazas.

As dusk falls, Old Montréal comes alive. Wander through Place Jacques-Cartier, browse boutique galleries and settle into an acclaimed restaurant like Monarque. Finish the night with a cocktail at The Coldroom speakeasy or atop a rooftop bar like Terrasse Nelligan with views of the Old Port. From intimate wine bars to fine-dining institutions, the experience is less about checking attractions off a list than letting the city reveal itself at its own pace.