2 Days in Toronto Plus Canada

Two days isn’t enough to see Toronto’s checklist, and honestly, that’s not what this trip is for. This version treats Toronto as the front door to Canada: one day meeting the country through what’s downtown, one day actually leaving it on a train.

Book these before you go

Day Focus Rough cost
1 Pearson arrival, Canada’s Walk of Fame, Hockey Hall of Fame CAD 12.35 UP Express + free sights
2 VIA Rail to Kingston, Fort Henry, waterfront VIA fare (book early) + Fort Henry admission

Day 1: Land, Clear Customs, Meet the Country

Morning

  • Pearson Airport (YYZ): Clear Canadian customs and immigration here, it’s the only passport check on this entire trip if you’re staying inside Canada. Then take the UP Express to Union Station, 25 minutes, every 15 minutes, 12.35 CAD one-way (9.25 with PRESTO), free for kids under 12.
  • Union Station: Take a minute in the great hall before you rush off. This is also the launch point for VIA Rail’s national network, which matters a lot tomorrow.

Afternoon

  • Canada’s Walk of Fame: A short walk from Union, King Street West between John and Simcoe holds 230-plus maple-leaf stars honoring Canadians who made it big, Gordon Lightfoot, Anne Murray, John Candy among them. Free, outdoors, and genuinely worth the detour.
  • Hockey Hall of Fame: Tucked inside Brookfield Place, this is where the actual Stanley Cup lives, not a replica. Hockey is Canada’s closest thing to a national religion, and seeing that trophy in person says more about this country than a shelf of guidebooks.

Evening

  • Downtown dinner: Pick anywhere near your hotel; Toronto’s real food identity is dozens of diaspora cuisines sitting side by side rather than one signature dish, so you can’t go far wrong.
  • Early night: Tomorrow’s train leaves early, so don’t overdo the nightlife.

Day 2: VIA Rail Day Trip to Kingston

Morning

  • Board VIA Rail at Union Station: Kingston is about two hours and fifteen minutes away, with two dozen departures a day, so an early train gets you a full day there. Economy gets you a reclining seat; Business (VIA1) adds a hot meal and lounge access if you want to splurge.
  • Fort Henry: A restored 19th-century fortress overlooking the St. Lawrence, and a solid morning stop once you arrive.

Afternoon

  • Kingston waterfront: Walk the harbourfront and take in the view toward the Thousand Islands. This is a genuine university and military town, a completely different pace from downtown Toronto twenty-four hours earlier.
  • Lunch in downtown Kingston: Small-city Ontario dining, none of the crowds you’d fight in Toronto.

Evening

  • Train back to Union: Grab an evening departure back to Toronto in time for a last dinner.
  • One last look downtown: If you’ve got energy, a walk past Union Station at night is a fitting close, since it’s the same building that just sent you out of the province and back.

Where to Stay

  • Downtown core hotels: The Fairmont Royal York, InterContinental Toronto Centre, or Sheraton Centre Toronto Hotel all put you within walking distance of Union Station, which matters more on this itinerary than usual.
  • Budget options: Hostels or Airbnbs near Union or the Financial District, still an easy walk to the train.

Things to Know

  • Passport: One check, at Pearson, on arrival. Nobody asks for it again on the VIA Rail leg since it’s all domestic travel.
  • HST: Ontario adds 13% at the register, not included in listed prices.
  • Tipping: 15-20% is standard at sit-down restaurants.

Getting Around

  • TTC: A single PRESTO tap costs 3.30 CAD, covering subway, streetcar, or bus.
  • VIA Rail: Book Kingston tickets ahead; fares climb fast the closer you get to departure day.

Tips

  • Book the Kingston train before you land: Seats and prices both tighten up closer to the date.
  • Don’t treat Toronto as just a layover: A day meeting the national identity here (Walk of Fame, the Stanley Cup, the sheer scale of the multiculturalism) sets up the train trip better than skipping straight to Kingston.
  • My take: two days is genuinely tight for this angle, but pairing one city day with one rail day gives you a real taste of “gateway to Canada” instead of just another downtown weekend.

Other Things of Interest

  • Queen’s Park: If you pass it, know it’s Ontario’s provincial legislature, not the national Parliament, that’s in Ottawa, about four and a half hours further down the same rail line if you ever extend this trip.
  • Longer trips: A 3-day version adds a full identity-focused day in Toronto before the Kingston leg.