Where to stay
The strong U.S. dollar means that you can splurge for less at places such as the design-forward Le Petit Hotel, in the historic district. Rates average $220 in September and October. For an Old World feel, try one of the 30 rooms in the Manoir Sherbrooke, housed in a century-old mansion in downtown Montreal. Rooms go for $90 to $128 a night in September and October.
What to do
Get your bearings at the new observation deck on the 46th floor of Au Sommet Place Ville Marie (tickets, $15). You’ll overlook some of Montreal’s iconic sites, such as the Gothic Revival Notre-Dame Basilica ($4 admission), which was founded in 1683, and the nine-mile Lachine Canal, flanked by a walking and biking path. For lunch, try Montreal’s signature sandwich, featuring a pastrami-like smoked meat, at the legendary Schwartz’s Deli ($7). Danny Pavlopoulos, co-founder of Spade & Palacio Non-Touristy Tours, recommends dinner at the Restaurant Le Diplomate.