Essential Toronto Itinerary: Downtown Core and the Financial District

In anticipation of so many friends and family coming to visit my fair city this summer, I’ve assembled a proper guide for the best things to see, do and of course, eat in Toronto. As a lawyer living and working in this crazy urban setting, I’m kicking off the series with an homage to my neighbourhood: the Downtown Core and the Financial District. 

Union Station

More likely than not, you will be coming to Toronto in some form or other through Union Station. This is the central hub of Toronto’s transportation system (although you’ll find that it’s really not in the “middle” of the city). Look into your public transportation options while you’re in the station, and don’t be surprised at how confusing the options are (yes, we still use tokens and have streetcars, but also have day passes, monthly metrocards, and a Prestopass system). Union Station has gone through massive renovations lately, and there are some nice and easy dining options here (try Amano for a proper meal, or Greenhouse Juice or Biscotteria Forno Cultura for something small and delightful. Pilot Coffee (in the train station part) or Balzac’s Coffee (near the UP Express train) are both great options for coffee.

Lunchtime Rush

After freshening up, take a short walk around the Financial District. If you find yourself caught in the rain or unbearable muggy heat, look for any sign that leads to “The Path” and discover where all of Toronto’s suits regularly go to for lunch. Otherwise, you might happily lose a few hours aimlessly wandering Toronto’s Eaton Centre at the intersection of Yonge and Dundas Street. Proper dining options are limited here, but Hokkaido Ramen Santouka is one of my favourite hidden spots at the southeast corner. If you find yourself closer to the Yonge and Queen Street intersection, the lower floor of Sak’s Fifth Avenue/Hudson’s Bay is also home to Sak’s Food Hall by Pusateri’s and these department stores also share a space with the beautiful South American Leña Restaurante. If you’re hanging out above ground, I would recommend Café PlentyDineen Coffee or Sud Forno Temperance for a small bite or caffeine fix. If you have a few moments to linger, head west on Temperance St. and enjoy a stylish afternoon at Boxcar Social. For a unique meal, head to the conceptual Assembly Chef’s Hall on Richmond Street where you will find outposts of many of Toronto’s best restaurants all in a common space.

Sud Forno at Yonge and Temperance
Sud Forno at Yonge and Temperance

The Main Attractions

The most obvious tourist attraction in Toronto is the CN Tower and most people can’t help but want to go up just to say they did. Keep in mind that it’s always more cost-effective to pair the visit with a meal or activity up there, as the price of the ride up will be included. If you have children or otherwise just like fish, check out Ripley’s Aquarium. Depending on the season (and the price you’re willing to pay), you may want to go to a Toronto Blue Jays game, a Toronto Raptors game, a Toronto Maple Leafs game.

If sports are not your thing, consider theatre, but book in advance! You can find information about all the shows happening in Toronto here. If the tickets you want are not available, perhaps you might opt for a film screening at TIFF Bell Lightbox, home of the Toronto International Film Festival. If you are having dinner beforehand, I would recommend LUMA Restaurant or Byblos for some finer dining, and Pai or La Carnita (if you can get a seat) for something more casual. FIGO is a good in-between option. I would strongly avoid blindly testing out any of the dated and “we don’t need to try” restaurants on Theatre Row.

If you want to do something even more high society, review the opera and ballet schedule at the Four Seasons Centre for the Performing Arts (and arrange to have dinner at Nota Bene if you do). 

Things to Walk By

There is really no need to drive in Downtown Toronto. Walking gives you a great opportunity to see landmarks such as Nathan Phillips Square (which turns into a great skating rink in winter, hosts festivals in the summer, and is home to the giant TORONTO sign) and Toronto’s Old and New City Halls. A personal favourite is Old Osgoode Hall (the original home of my law school) which is now home the Ontario Court of Appeal and the Law Society of Ontario. There is an excellent restaurant within. Many people either don’t know about it, or assume it’s only for lawyers, but it’s actually open to the public during regular lunch hours. Though it can be a bit hectic and overly-touristy at times, there are often fun events happening at Yonge-Dundas Square  (think of it as a try-hard Times Square of the North). My favourite place to stop and stare downtown is at Berczy Park, more lovingly dubbed the “Dog Fountain”, located just east of Yonge and along Front Street. There are few urban places as happy as this little piece of land.

For Your Business Dinner

If you’re going to be spending the evening in this area, it is likely that you’re here for a business trip or conference, and you need a restaurant to match the occasion. I recommend Richmond Station for almost anyone, anytime. Buca, Marben, or Woods Restaurant are all excellent options as well. If your budget or expense account is generous, you might also consider a reservation at Canoe, Bymark or The Chase. All seven of these restaurants (with the exception of Buca which is purely Italian) serve contemporary Canadian food. If you’d prefer something Japanese, JaBistro and Miku are two of the best high-end sushi restaurants in Toronto. An honourable mention goes to the slightly more casual French gastropub called The Gabardine


The newly-opened Walrus Pub & Beer Hall and King Taps should be considered your go-to places to feel comfortably overcrowded and get up close and personal with the Bay Street crowd. If your evening is continuing past 10:00 PM, the bars and clubs on King Street West are your best bet (though be warned that many of them take themselves very seriously and have dress codes to match). I would recommend Baro (great things to eat here as well), WVRST (fancy sausages and beer), The Addison’s Residence (like you’re going to your wealthy friend’s parent’s house), The Citizen (a classic option), Bar Hop (a bit more casual) or SPiN Toronto (this is Susan Sarandon’s ping pong club. Yes, it’s a real thing, and you will need to reserve well in advance). Whatever club you end up in afterwards is up to you. If you’re closer to Yonge and Front Street and want to avoid all of the King West noise, D.W. Alexander is a casual and modern speak-easy style bar, The Reservoir Lounge is great for jazz music, and Pravda Vodka House is a strange place but great for any true vodka lover. All three of these places are located near Berczy Park. 

Final Notes (and What to Avoid)

There are so many great restaurants in Toronto that it would be a shame for you to end up at a bad chain restaurant (read my little guide here), and unfortunately, the Downtown Core is full of them. If the restaurant you’re contemplating seems too big and generic, it probably is.

If you get lost, most people are more than willing to provide you with directions. However, if you start to feel that Torontonians seem unfriendly, it is likely because you’re walking too slowly and blocking someone’s path to the meeting they’re late for. Keep to the right side of the sidewalk at a comfortably brisk pace, and you’ll find that everyone will seem a lot friendlier. 

Up next: Essential Toronto Itinerary: Distillery District and Canary District

[small]Disclaimer: some of these places above are partially-owned by some of the partners at my law firm, but they did not have any involvement in the drafting of this post. For what it’s worth, there are also places that they own that didn’t make the list! Further note: I have not included Edulis and Alo, two of the best restaurants in Toronto, on this list, because the reservation process is quite challenging. If you have the ability to book, I would encourage it! Financial District photo credit: Al x on Unsplash[/small]


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