Old Montreal has a reputation problem: tourists see the horse carriages and cobblestones and assume that's the whole story. It isn't. There's a genuinely good 48 hours to be had here — you just have to walk two blocks off the main strip to find it.
Friday evening: Arrive without a dinner reservation on purpose. Walk toward Rue Notre-Dame instead of Rue Saint-Paul, and pick whichever wine bar has the shortest, most confident-looking menu.
Saturday: Morning market run, then an afternoon that has nothing to do with a checklist — this is a neighbourhood built for wandering, not scheduling. Save the evening for a tasting menu you booked weeks ago, because the good ones fill up fast.
Sunday: A slow brunch, not a rushed one. Then leave before the day-trippers arrive and the neighbourhood turns back into a postcard.
Full itinerary — with the specific streets, the reservation you need to make in advance, and the one you shouldn't bother booking — in the guide.