72 Hours in Toronto

Our Thoughts

Here’s how to make the most of your three days in The Big Smoke.

To celebrate a friend’s milestone birthday—and for a much needed change in scenery during the pandemic—I flew from YVR to YYZ at the end of the summer to enjoy an extended weekend of café hopping, sightseeing and shopping.

Arrival, Transportation and Where to Stay

We checked into our hotel, the Fairmont Hotel York, at 5:30 p.m. Arriving from Pearson International was a breeze—we took public transportation four stops to Union Station and conveniently crossed the road to our hotel.

TLW tip: Avoid Toronto’s notoriously terrible traffic and enjoy the 30 minute train ride to your hotel.

The weather was unseasonably warm (and luckily we missed the record-breaking rain in Vancouver), so we checked in, changed and headed out for dinner at Richmond Station. Unfortunately, the great reviews weren’t an accurate representation of the meal we were served. The Thai fried chicken and cabbage salad was lackluster, but the patio seating in the Financial District and people watching somewhat made up for it.
From there, dessert was in order. I highly recommend Butter Baker—the lineup out the door was warranted. We took our dessert to go, enjoying it in the Entertainment District, below skyscraping billboards.From there, we wrapped the night with a nightcap at Coffee Oyster Champagne.

Committed to transiting on foot for the duration of our trip, we wandered through the historic Hudson’s Bay, past old and new City Hall buildings and Nathan Phillips Square before calling it quits and heading to bed in preparation for a fresh start the next day.

Day One

Our first day in Toronto started with an early morning 35-minute walk from York Hotel to Chinatown and Kensington Market for a bagel from Nu Bagel paired with Dark City Coffee brew. Dark City Coffee, originating from just outside of Toronto, is the most unique coffee I’ve tried—in fact, it doesn’t really taste like coffee. Try it yourself at Nu Bagel, or other local cafés.

Kensington Market in the morning was calming—sitting in the sunshine on a patio and watching shopkeeper’s prepare for the day ahead. It’s a street lined with local vendors and restaurants, and you just knew it comes to life at night. From there we visited Casa Loma, a Gothic Revival style castle mansion.

Arriving early in the morning was to our advantage; there were fewer people milling about as we enjoyed a lengthy walk through the castle’s four stories and outdoor towers, via audio guide. For those that enjoy history and luxury, this is the place for you. Envelope yourself in the old days as you imagine living life in a mansion overlooking Toronto. Casa Loma will cost you $30 to enter.

Finishing up at the castle, we walked about 35 minutes to Yorkville and the Annex, where we scoped out the high-end shops located on Bloor Street West. On our way, we walked down Hazelton Avenue. If you’re a fan of unique, character homes, be sure to stroll through this picturesque neighbourhood.

After a few hours of browsing we stopped at Sassafraz for lunch, which I highly recommend, but expect a wait. In need of a post lunch buzz, we popped to Holt Café for a latte where the service, and coffee, outshone any other establishment on the trip.

Finally it was back to the hotel to prepare for the evening.

The evening took us to the CN Tower where we watched the sun set. Test your bravery walking over the see-through floor, and if you feel so inclined, have a refreshment at the top and take it all in. I’m one for city views, so at $40, this attraction was a must for me.

We went to nearby Scaddabush for a late dinner. I wouldn’t recommend the place, but if you do stumble upon it, try their pizza.
With day one in the 6ix in the books, it was time to get some rest before taking on day two.

Day Two

Day two was my favourite of the trip. We started off with a Balzac’s oat milk latte, then carried on touring through St. Lawrence Market, and stopping to admire the architecture (Gooderham Building) of the Distillery District.

St. Lawrence Market is mostly made up of local grocers, rather than restaurants and souvenir shops. If you’re looking to do some shopping, venture around the neighbourhood—I picked up a beautiful blue, lace dress in the area.

The Distillery District is one of the five must see neighbourhoods of Toronto, along with the Entertainment District, Yorkville + the Annex, Chinatown + Kensington Market + AGO District and Queen West + King West + Liberty Village.

Before leaving the Distillery District we had lunch at Hot House and again, were disappointed by the misleading reviews.

From there we took the ferry to Centre Island from Jack Layton Ferry Terminal. The round trip cost us $8.50 each and was well worth it.

Toronto Island was majestic. We headed left after exiting the ferry, enjoying the amusement park and petting zoo views and watching those playing disc golf and enjoying water sports. Without intention, we walked the entire Island, stopping at The Island Café for an espresso and cookie (don’t miss it!), and enjoying the waterside promenade and pier.

After many hours on Toronto Island, we took to the city, cruising King Street at night (party central for those who are interested) and popping into Gusto 101 for dessert before calling it.

Day Three

We started our final day in T.O. at Louix Louis located on the 31st floor of the St. Regis Hotel. After some overpriced avocado toast and coffee, we headed to Queen Street for some shopping.

Queen Street was lovely—endless boutiques and no shortage of homegrown coffee shops. After picking up a pair of perfectly fitting jeans and a few vintage sports tees, we headed back into town, stopping at Dineen Coffee Co. It’s highly rated, and there’s no shortage of patrons, inside and outside the old world charm café.

After the caffeine, we decided to head for a late lunch and waterfront walk before grabbing our stored bags from the Fairmont Hotel York.

The Cavolo Nero salad from Cafe Oro di Napoli near the East Bayfront area was arguably the best salad I’ve ever had at a restaurant. Sitting on the patio, I took in my final few moments in Toronto, watching the restaurant churn out smiling, gelato licking customers.

Toronto, Summarized: What You Can’t Miss

You can absolutely get a solid feel for Toronto in 72 hours. Here’s what you won’t want to miss:

  • CN Tower
  • Toronto Island Park
  • The Island Cafe
  • Butter Baker
  • Cafe Oro di Napoli
  • A stroll on Toronto’s waterfront
  • Shopping Queen’s Street and for wanderers with deeper pockets, Bloor Street West

Deana Srdic

Deana is a writer, content marketer, operations manager, and big dreamer. For her, travel amounts to architecture gazing, market shopping and people watching at sidewalk cafés. Most importantly, when traveling she wanders endlessly on foot.

Reader Interactions

Leave a Reply