Depart Toronto early. The drive to Montréal is about 5h 49m (543 km) straight up Highway 401 and across into Quebec on the 20, though weekend traffic can add 30 to 60 minutes, so budget closer to six and a half hours. If you'd rather skip the wheel entirely, VIA Rail runs the same corridor in roughly five hours and drops you at Gare Centrale downtown. Either way, aim to arrive by early afternoon and drop your bag in the Plateau-Mont-Royal, your home base for the weekend, all leafy triplex staircases and neighbourhood cafés.

Shake off the trip with a proper introduction to the old city. Take a self-guided wander through Vieux-Montréal, following the cobblestone lanes past the basilica and down to the waterfront, soaking up the stories in the architecture along the way. Pack a light rain jacket, it's 22°C but there's a 24% chance of drizzle, so the stones will glisten. Rainy day alternative: duck into the Pointe-à-Callière archaeology museum on Place Royale.

Duck into Bonsecours Market, the silver-domed 1847 hall on Rue Saint-Paul. Browse Quebec artisan stalls, then step out to the waterfront promenade of the Old Port of Montreal for golden-hour views across the river as the day-trippers thin out.

Dinner at Modavie on the corner of Saint-Paul, a warm bistro with nightly live jazz, ideal for solo dining at the bar with a plate of lamb and a glass of something local. If Modavie is fully booked or closed, try Gibbys or another Old Montreal bistro nearby. Afterward, ride the metro up to the Plateau for late drinks along Boulevard Saint-Laurent, where the bars stay loud past midnight.

Start where locals do. Take the metro to Jean-Talon station and lose yourself in Jean Talon Market, one of North America's great open-air markets. Graze on Quebec cheeses, fresh cider, and a warm pastry between the produce stalls. Arrive before 10am to beat the weekend crowds, it gets shoulder-to-shoulder by midday. Confirm hours before visiting.

Time for culture. Head to the Montreal Museum of Fine Arts on Rue Sherbrooke ($24 admission), a sprawling, free-flowing collection across several pavilions, an easy, absorbing few hours and a smart move given the 18°C drizzly forecast.

Cross town to Marché Atwater, the art-deco market hall by the Lachine Canal. Grab a coffee, walk a stretch of the canal path, and watch cyclists roll past the water as the light softens. Rainy day alternative: linger inside the market hall's food stalls and specialty vendors.

Dinner at Au Pied de Cochon on Avenue Duluth, the temple of unapologetic Québécois indulgence, foie gras, duck, poutine, and a buzzing counter that's perfectly comfortable solo. Confirm hours before visiting, as they vary. If Au Pied de Cochon is fully booked or closed, try L'Express nearby. Then walk it off toward Saint-Laurent for nightlife, or catch live music at a Plateau bar to round out the night.

Ease into the day with a stroll through the Plateau to La Maison Rose, the beloved candy-pink corner house on Rue Saint-Ambroise, one of the city's most photographed and quietly charming spots. Grab brunch at a neighbourhood café nearby before the weekend crowds wake.

Squeeze in one last classic: Schwartz's Deli on Boulevard Saint-Laurent for a hand-carved smoked-meat sandwich, an institution since 1928. Counter seating means solo travelers slot right in. If the line at Schwartz's is out the door, try Lester's Deli or grab a sandwich to go. Take a final unhurried wander down Saint-Laurent afterward.

Aim to leave Montréal by 2:00pm to beat Sunday-evening traffic. Retrace your route west on Autoroute 20 to Highway 401, roughly a six-hour drive back to Toronto (longer if weekend traffic bites). If you want a stretch break, the town of Kingston at the halfway mark makes a pleasant waterfront pause before the final leg home.