Montreal rewards visitors who plan around its seasons. May through October gives you terrasses, festivals and the Old Port at its best; December through March gives you a quieter, genuinely beautiful winter city — provided your transport is winter-equipped.
Base yourself downtown or in Old Montreal. Downtown puts you near the Bell Centre and the Golden Square Mile; Old Montreal gives you cobblestone streets, the Notre-Dame Basilica and the finest boutique hotels in the city.
A strong three-day chauffeured itinerary: Old Montreal and the Basilica on day one, Mount Royal lookout and the Plateau's Mile End on day two, and a Laurentians run to Mont-Tremblant on day three.
Keep a chauffeur on hourly service for at least one of those days. Parking in Old Montreal is genuinely difficult, and being dropped at each door turns a logistics exercise back into a holiday.
