After landing at Toronto Pearson Airport, keep things easy and take the UP Express straight to Union Station. It’s usually the fastest, least stressful option into downtown, especially when traffic on the 401 is doing its usual thing. Trains run about every 15 minutes, the ride is roughly 25 minutes, and a one-way fare is typically around CAD 12–13. Once you’re downtown, you’ll be close to St. Lawrence and can check in, drop your bags, and get your bearings without losing the whole first day to transit.
Head over to St. Lawrence Market for a first taste of the city. If you’re arriving on the later side, don’t worry about doing the whole market like a mission—this is more about an easy wander and grabbing a casual dinner than ticking off every stall. The market is especially good for simple, satisfying food: peameal bacon sandwiches, fresh pasta, pastries, or something quick from one of the prepared counters. Most vendors close by early evening, so aim to get there before it gets too late. Budget about CAD 15–25 if you’re eating casually, a little more if you make it a fuller meal.
From there, walk a few minutes to Berczy Park to stretch your legs. It’s small, but it’s one of those little downtown parks people quietly love, mostly for the whimsical dog fountain and the nice view lines toward the old core. A 20-minute stop is enough unless you’re jet-lagged and happy to sit longer. Then continue to C'est What? for your first proper Toronto pint and a relaxed dinner. It’s a very local-feeling spot for Ontario craft beer, with a menu that leans hearty and pub-friendly; expect around CAD 30–45 per person. If you’d rather do something a touch more polished, swap dinner for The Keg Mansion in the Garden District—it’s a beautiful old house and a classic first-night steakhouse choice, usually in the CAD 45–70 range. Either way, keep the evening light and leave some room to wander back through the downtown streets after dinner.