Toronto Itinerary: How to Spend a Weekend in Toronto

by May 20, 2020Stopovers & Layovers, Canada, Toronto, Weekend Getaways22 comments

After so many years of travelling, I can’t believe it’s taken me this long to put together a 48 hour Toronto itinerary. It’s where I was born, and it’s where I live, work and play, you’d think it would be easy to put together a list where to go in Toronto, right? Well, it is, and it isn’t. 

Toronto is a world-class city in its own right, but for me, when I return from a trip, I want to relax and slowly try to get back into the groove of the daily grind. But as a travel blogger who creates short trips, mini-breaks, business travel and weekend getaway itineraries, I’m sort of obligated to create an itinerary for Toronto.

All that said, I live in a massive city, so I decided to stick with the downtown Toronto attractions instead of things to do near Toronto. Some are Toronto tourist spots, while others are hidden gems that only a local like me would know.

 Also, our national airline Air Canada is allowing you to hook up a stopover for up to 7 days in Toronto on your way to Europe or Asia. Sweet! 

You can bookmark this itinerary for when you get here. Hell, I’ll even welcome you at the airport with open arms.

This article is now available as a mobile app. Go to GPSmyCity to download the app for GPS-assisted travel directions to the attractions featured in this article.

Toronto History

  • Toronto is the capital of the province of Ontario and the most populated and most famous (forgot to remove my bias) city in Canada. This probably is the reason why most Torontonians think that Toronto IS Canada.  
  • Despite Toronto’s population, popularity and Torontonians’ feelings on the matter, It is not the nation’s capital. That would be Ottawa, the seat of Canada’s federal government.
  • The name of Toronto or “Taronto” once referred to a channel of water between Lake Simcoe and Couchiching, which has been listed on maps as early as 1675. The name eventually travelled South to a fort at the mouth of the Humber River. Fort Toronto was the first settlement in the area thus becoming the name of the most magnificent city on earth Toronto (again forgot to remove my bias)
toronto itinerary

Fort York

PLACES TO STAY IN DOWNTOWN TORONTO

Fairmont Royal York Hotel

Fairmont’s historic ballroom is legendary and the hotel itself is a city icon.  Its spacious rooms feature floral accents and include designer bath toiletries and robes. It has a skylit indoor pool, 5 on-site dining options, its across the street from Union Station with shuttle bus to both airports.

Check Rates & Availability

Thompson Toronto

The Hotel has a rooftop pool and bars with views of the city and CN Towers – I could pretty much stop there. But, it has designer linens and bath amenities. Fully stocked minibars, 24-hour concierge, on-site valet and a 10-minute walk from the bars and restaurants of King West.

Check Rates & Availability

Hyatt Regency Toronto

Located in the entertainment district in the centre of Toronto – trust me there is no better place to be. It’s a modern hotel with flat-screen TVs and Apple docking stations,  on-site sauna, outdoor pool and it’s King Street Social Kitchen and Lounge serves regional cuisine.

Check Rates & Availability
Thompson Toronto places to stay in downtown toronto

THOMPSON TORONTO – Infinity pool

GETTING TO TORONTO

Plane

Toronto has two main airports Toronto Pearson International Airport and Billy Bishop Toronto City Airport. Toronto Pearson is Canada’s principal airports with flights to every continent and over 76 scheduled and charter airlines. Canada’s flagship airline is Air Canada, which allows you to hook up a stopover for up to 7 days in Toronto on your way to Europe or Asia.

Sure, you can take a taxi, Uber or public transportation from the airport to Toronto. Still, the fastest and most cost-effective way is the UP Express (Union-Pearson Express). UP Express is a rail service that connects Toronto’s central train station (Union Station) with Toronto’s main airport.

Billy Bishop, Toronto City Airport, is located on Toronto Island, which minutes from the downtown core. A short ferry ride or a quick stroll through the pedestrian tunnel that runs under Lake Ontario will get you into Toronto. Both Porter Airlines and Air Canada serve the airport.

Train

VIA Rail and AMTRAK will get you into the heart of the city via Toronto’s Union Station. Union Station is connected to both Toronto’s Subway (TTC) and the underground walking network (PATH

GO Train connects Toronto with several other cities and towns around Ontario including Niagara Falls. 

Car

Several highways, including Highways 2, 401, 407 and the Queen Elizabeth Way, link surrounding cities to Toronto. The nearest Canada-U.S. border crossings are at Niagara Falls, Fort Erie and Windsor.

Bus

The Toronto Coach Terminal, once called the Gray Coach Terminal, is Toronto’s central bus station. It is connected via the underground PATH and sits between two Subway Stations. The terminal is used Coach CanadaGreyhound Canada, and Ontario Northland bus lines.

billy bishop airport and things to do in toronto

Billy Bishop Airport

BEST WAYS TO GET AROUND TORONTO

  • Foot. Walking or even crawling will probably get around the downtown core the fastest. Luckily the majority of most popular sites on this Toronto Itinerary are within walking distance or require minimal public transportation. Another option is The PATH is a massive underground pedestrian walkway that spans more than 30 kilometres. In the PATH, you’ll find restaurants, shopping, services, entertainment and connections to public transit. Check out the map HERE
  • Bike. Biking, rollerblading, skateboarding or electric scooter/bike around the downtown core is the absolute best transportation option. 
  • Car. Please don’t. Unfortunately, with copious amounts of construction and a poorly planned city, traffic is horrendous. It takes one hour to get from Toronto to Toronto in any direction – on a good day, any day, any time. Give yourself at least an hour (not including travel time) to get to your destination. Best case scenario you’ll arrive an hour early, worst case scenario you’ll arrive on time. That said, parking is not any better and presents its particular piece of hell. Parking is at a premium, and in addition to the lack of available spaces, it’s quite expensive in private parking lots. Whenever possible, look for GreenP parking lots or GreenP street metered parking as it is run by the City of Toronto and cheaper than private parking. You could use the GreenP app to find and pay for parking if you were lucky enough to score a spot.  
  • Public Transportation. The subway should technically be the perfect solution. Well, it’s not. It’s better than nothing but its often crowded, severely underserves a city this size in terms of capacity and coverage and it’s a constant work in progress. It is currently in the middle of a much-needed extension, but as of now, its a pain point. The bus and streetcar/tram surface routes (except for two specific streetcar lines) are subject to the same traffic issues as the cars.
  • Boat. I tried to fit a boat tour in the itinerary, but unfortunately, it was one of the things I needed to cut. That said, one of the best ways to see Toronto’s beautiful skyline is from Lake Ontario or Toronto Islands. From the Toronto harbour, you can book Mariposa CruisesToronto Harbour Tours, Empress Of Canadaor the traditional 165-foot three-masted schooner (which you’ll find engraved on Canada’s ten-cent coin) the Tall Ship Kajama
street car - BEST WAYS TO GET AROUND TORONTO

THINGS TO KNOW ABOUT TORONTO

  • Construction. Let’s get the bad stuff out of the way first. Development here in Toronto has its very own year-round season; Spring, Summer, Fall, Winter & Construction. When you look around, you can see dozens of cranes cluttering the skyline with condominiums being built at an alarming speed – which most consider a good thing. But with growing pains come watermain repairs, street repairs, bridge repairs and subway extension projects, getting around the city by car and at times public transportation can be challenging. (As mentioned above) 
  • Pronunciation. “Chrrr-runo” is the way we pronounce Toronto. We can usually tell who’s not from here as visitors tend to emphasize the T’s.    
  • As mentioned above Toronto is the best-known city in Canada, which usually leads to other cities, towns and villages hating us and our sports teams – especially the Toronto Maple Leafs (hockey). The Blue Jays and the Raptors (baseball and basketball respectively) are exempt as they are the only National teams Canada has. 
  • Speaking of the Toronto Raptors, they were 2019 world champions! “WE THE NORTH!”
  • Neighbourhoods. One of Toronto’s greatest treasures is its communities, which at times can be looked at like mini-cities or mini-countries in some cases. Unofficial known as “the city of neighbourhoods.” we have 140 neighbourhoods officially recognized and about 240 official and informal communities within the city. French is Canada’s official second language, but not everyone speaks French. Without getting into the countries ugly colonial past involving French & English empires and the mistreatment of indigenous peoples. Some tensions remain between French and English Canada (often represented by Quebec and Ontario). Some times the language difference rares its ugly head culturally, politically and definitely during hockey games. In Toronto, however, we speak English.
  • Diversity Equals Great Food. Not all Torontonians are friendly people. We are not as aggressive as NYC, but we are not that far off. What is considered “polite” here in Toronto is more like the American’s Southern Insult – Good Bless Your Heart. There’s almost nothing that will unite Canadians faster than if someone comments on certain similarities between Canada and the United States. Quietly defining their distinctions from their southern neighbours has been a part of the Canadian experience of national identity since 1867. Yes, some Canadian accents may sound similar to some American ones, and on the surface, a megacity such as Toronto might reflect the generic “look” of a North American city, but historically, politically, and socially, Canadians are proud of their country and its differences.
  • Raccoons. Raccoons rule the city, and in fact, I’m not opposed to having our national animal the beaver being replaced with a raccoon. For they are smart enough to get past border security at Toronto Pearson International Airport. 
toronto raptors - fun activities in toronto

Day 1

Toronto Itinerary

Baldwin Steps

The first stop is Casa Loma but in order to get up the hill, we need to use the Baldwin Steps, which are a public outdoor staircase that dates back to the 19th century. They are named after a former landowner of the area, the Baldwin family, which included Robert Baldwin, a former premier of Ontario.

toronto places to visit baldwin steps

Casa Loma

This 98-room castle was commissioned by Sir Henry Mill Pellatt, a Canadian soldier, and investor who founded the Toronto Electric Light Company in 1883. Sir Henry Mill Pellatt ordered Toronto native and architect E. J. Lennox to design Casa Loma. The 3.5 million dollar castle began construction in 1911 and was finally completed by 1914. Today Casa Loma is used as a filming location, a museum, as a venue for weddings. It is also one of Toronto’s most popular landmarks.

casa loma things to do in toronto ontario
toronto itinerary - casa loma
casa loma things to do in toronto ontario

Royal Ontario Museum (R.O.M.)

The Royal Ontario Museum is one of the largest museums in North America and the largest museum in Canada. The ROM is highly regarded as a “preeminent field research institute and an international leader in new and original findings in biodiversity, paleontology, earth sciences, the visual arts, material culture, and archaeology”.

Royal ontario museum what to see in downtown toronto
Royal ontario museum what to see in downtown toronto
Royal ontario museum what to see in downtown toronto

University Ave. South from Bloor St.

university street south - toronto itinerary

Philosophers Walk (*Hidden Gem)

The Philosophers Walk is a scenic footpath located in the St George campus of the University of Toronto.  It runs north-south along what was once natural water called Taddle Creek, which was buried during the industrial age and now flows underwater.

philosopher's places to visit around toronto
philosopher's walk places to visit around toronto
philosopher's walk places to visit around toronto

Legislative Assembly of Ontario & Queens Park – Beside The University Of Toronto Campus

LEGISLATIVE ASSEMBLY OF ONTARIO & QUEENS PARK

University of Toronto (Campus)

The University of Toronto was originally founded in 1827 as King’s College and as the first institution of higher learning in Upper Canada. The university is comprised of twelve colleges. The University of Toronto also has two satellite campuses located in Scarborough and Mississauga.

university of toronto campus - places to explore in toronto
university of toronto campus - places to explore in toronto
university of toronto campus - places to explore in toronto

View of Toronto from University of Toronto Campus

university of toronto campus - places to explore in toronto

Baldwin Street, Restaurants (*Hidden Gem)

Yes, you might have guessed it’s the same Baldwin family who owned the land that the steps used to get to Casa Loma are built on. This small Toronto enclave is located in Toronto’s Grange Park neighbourhood. Baldwin Village is famous for its small shops and restaurants like, Shawarma and Falafel Place, Chardise, Sid’s Deli, and many other favourited restaurants of Toronto. 

baldwin st - toronto where to go
baldwin st - toronto where to go
baldwin st - toronto where to go

Kensington Market

Kensington Market is Toronto’s self-proclaimed “most vibrant and diverse neighbourhood”.  This bustling Toronto neighbourhood serves as a fine indicator of Toronto’s multicultural diversity. No establishment in Kensington Market is the same. Vendors, shops, and restaurants of all sorts of ethnicities make up the melting pot that is Toronto’s “most vibrant and diverse neighbourhood”.

Kensington market - best things to do in toronto
Kensington market - best things to do in toronto
Kensington market - best things to do in toronto
Kensington market - best things to do in toronto

Art Gallery of Ontario (AGO)

The Art Gallery of Ontario (AGO) is home to over 90,000 different artworks and is lauded as one of North America’s most distinguished art museums.  This massive museum carried works of art that range from the Renaissance to contemporary pieces of art. Aside from being an astonishing physical museum, AGO also has launched its social media website called Collection X, which grants users access to a digital art forum that is opened to artists and art lovers.

ago - art gallery of toronto - toronto art museum
ago - art gallery of toronto - toronto art museum

Grange Park

Right beside the AGO is OCAD U (The Ontario College of Art and Design University) and right behind that is Grange Park which happens to my local park. 

Many-a-blog-post was conceived in this park!

There are two large sculptures by world-famous sculpture, Henry Moore and 14 nature related, inscribed granite paving stones from famous Canadian authors. 

ago - art gallery of toronto - toronto art museum
ago - art gallery of toronto - toronto art museum
ago - art gallery of toronto - toronto art museum

Queen Street West

Named “the second coolest neighbourhood in the world” by Vogue magazine, Queen Street West in downtown Toronto’s most celebrated (fashion) district. Queen Street West is a hip, urban strip that extends for two kilometres (1.25 miles) between Bathurst and Gladstone and is comprised of some of the city’s most trendy boutiques, art galleries, bars, and restaurants.

queen st west - where to go in toronto
queen st west - where to go in toronto
queen st west - where to go in toronto

Graffiti Alley (*Hidden Gem)

Just south of Queen Street West is one of Toronto’s most surprisingly artistic accomplishments: Graffiti Alley. Graffiti Alley stretches for approximately one kilometre (.6 miles) and is teeming with urban art that is (legally) painted each summer by an artistic troupe called Style in Progress. If you’re looking to explore Toronto in hopes of finding a hidden gem that reflects the urban, artistic capabilities of the city, then Graffiti Alley is that and more. Read more about Graffiti Alley from my post: Toronto’s Graffiti And Street Art

graffiti alley - stuff to do in toronto
graffiti alley - stuff to do in toronto
graffiti alley - stuff to do in toronto

King Street West | King West Village

King West Village is one of Toronto’s fastest-growing communities. With waves of young professionals moving into the neighbourhood, Kings West Village has experienced a boost in its economy and social scene. Aside from the rapidly changing demographic of the neighbourhood, King West Village is well-known for its landmarks, 19th-century buildings, and iconic brownstones.

King West - fun places in toronto

Rogers Centre (a.k.a. The SkyDome)

Opened in June 1989 and originally named the SkyDome, Rogers Centre is a multi-purpose indoor stadium that holds some of Toronto’s wonderfully exciting venues. Notably, the Rogers Centre is home to the Toronto Blue Jays (MLB) and has served as the venue for an array of different events: sporting events, concerts, auto shows, circuses, Disney on Ice, and much more.

Architecturally, the stadium is well-known for being the first stadium to have a fully retractable motorized roof, having an annexed 348-room hotel attached, and is also the last dual sporting major-league stadiums in North American (MLB and NFL).
Rogers centre skydome - stuff to do in toronto

Toronto Railway Museum

The Toronto Railway Museum, a mainstay attraction of downtown Toronto located in Roundhouse Park,  is “dedicated to preserving the physical legacy, history, and experience of rail transportation in Toronto and Ontario.” The museum has lots to offer, such as a railway simulator, in-depth historical displays, and interactive displays. Be sure to check out the gift shop and go on a Miniature Train ride before you leave!

roundhouse - tourist sites in toronto
roundhouse - tourist sites in toronto

CN Tower | 360 Restaurant

Often viewed as the pride and joy of Toronto, The CN Tower is a spectacular architectural and engineering feat that captures the livelihood of the city. This national icon and landmark are well-known for its (cost-efficient) state-of-the-art LED lighting system, as well as recently being on the cover of Drake’s critically-acclaimed album “Views”.  Aside from its stature as a culture and urban icon, the CN Tower is home to the revolving 360 The Restaurant.  This world-class restaurant is managed by Executive Chef John Morris and General Manager of Restaurants and Events Cameron Dryburgh, who helms the culinary team at the award-winning restaurant.

cn tower - top sights in toronto
cn tower - top sights in toronto
cn tower - top sights in toronto

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Day 2

Toronto Itinerary

Distillery District 

Despite its name, Toronto’s Distillery District is known for being “Canada’s premier arts, culture and entertainment destination”.  The district gets its name from the 47 buildings that were formally known as the Gooderham & Worts Distillery. Since 2003, the Distillery District has been offering locals and visitors a “hip, cool dynamic” that is comparable to New York City’s SoHo or Chelsea. Be sure to check out the Distillery District’s unique shops, galleries, studios, restaurants, cafes, theatres, and more!

distillery district - things to see in toronto
distillery district - things to see in toronto
distillery district - things to see in toronto
distillery district - things to see in toronto

Balzac’s Coffee – Distillery District 

balzacs - places to go in toronto
balzacs - places to go in toronto

St. Lawrence Market

The St. Lawrence Market is an encompassing, nostalgic shopping destination in Toronto. The market is made up of three main buildings that each provide their own unique services and products: The South Market, the North Market and St. Lawrence Hall. The South Market is known for having vendors that sell fresh produce, meat, fish, grains, baked goods, dairy products, as well as non-food items.

The second floor of the South Market, home to the Market Gallery, serves as an exhibition space for the City of Toronto’s Cultural Services. The North Market is well-known for its Saturday Farmers’ Market, Sunday antique dealers, rental spaces. St. Lawrence Hall is comprised of various retailers on the ground floor, city offices on the second floor, and auxiliary rooms for special events on the third floor.

toronto itinerary
st. lawrence market - where to go in toronto
st. lawrence market - where to go in toronto
st. lawrence market - where to go in toronto

Gooderham Building 

Toronto’s Gooderham Building, also known as the Flatiron Building, is one of the city’s historical landmarks. Located in Toronto’s Financial District, the Gooderham Building was completed in 1892 as a premature model of its current architectural state. Now, the building serves as not only an office building but as a historical landmark that adds to Toronto’s pizzazz.

gooderham building - toronto points of interest
gooderham building - toronto points of interest

Cathedral Church of St. James

Opened on June 19, 1853, the Cathedral Church of St. James stands as one of the largest Toronto-built buildings. The Cathedral was constructed with the intention of replicating Gothic Revival architecture. The cathedral is well-known for its 92.9 meters (305 foot) tower and pointed spire.

st, james - toronto points of interest

Yonge-Dundas Square

Yonge-Dundas Square is Toronto’s equivalent of New York City’s Times Square. This bustling, vibrant square experiences fluxes of tourists and locals who relish in the square’s open space and eccentric ambiance. Yonge-Dundas Square’s myriad of LCD displays brings a one-of-a-kind luminescence to Toronto and capture’s the city’s animated downtown vibe

dundas square - toronto points of interest
dundas square - toronto points of interest
dundas square - toronto points of interest

Eaton Centre 

Located in downtown Toronto, the Eaton Centre is Toronto’s only mega shopping centre. This massive shopping centre is home to over 230 national and international retailers, as well as offering patrons tons of dining and entertainment options.

eaton centre - toronto places to visit
eaton centre - toronto places to visit

Old City Hall

Old City Hall is just one of four city halls to be constructed in Toronto. The building boasts a Romanesque style of architecture, as well as a distinguishable clock tower. Since 1984, Old City Hall has been designated as a National Historic Site of Toronto.

old city hall - toronto itinerary

Old City Hall & New City Hall

old city hall - toronto itinerary

Toronto City Hall | Toronto Sign

Toronto City Hall, also known as New City Hall, serves as the home of Toronto’s municipal government.  Despite its round base, Toronto City Hall is comprised of two towers that are curved in, and stand at varying heights. Toronto City Hall’s courtyard, Nathan Phillips Square, serves as the primary host of various festivals and events in Toronto.

toronto city hall - toronto itinerary

Yonge St.

Centred around Yonge-Dundas Square is Yonge Street. As is typical of the streets of downtown Toronto, Yonge Street is lined with heaps of restaurants, bars, and shops. Yonge Street is one of Toronto’s main streets, it is the longest street in the world and divides the city between East & West.

yonge st - downtown toronto attractions
yonge st - downtown toronto attractions
yonge st - downtown toronto attractions

Hockey Hall of Fame

In the typical Canadian fashion, Toronto is home to the Hockey Hall of Fame (HHoF). The Hockey Hall of Fame building was established in 1943 and is located on Yonge Street. The HHoF houses 15 various exhibit areas that cover 60,000 square feet. Visitors of the HHoF can view trophy displays, memorabilia, and player equipment worn during special games. The Hockey Hall of Fame also has an interactive display called “Be a Player” that allows patrons to use shoot real pukes against a simulated legendary goaltender, Ed Belfour.

hockey hall of fame - yonge st - downtown toronto attractions
hockey hall of fame - yonge st - downtown toronto attractions
hockey hall of fame - yonge st - downtown toronto attractions

Union Station

union station - places in toronto

Harbourfront | Harbour Centre

The Harbourfront Centre is nonprofit cultural organizations that put together events and activities to enrichen and enhance downtown Toronto. Located at 235 Queens Quay West, on Toronto’s waterfront, the Harbourfront Centre is a must-visit destination for all those looking to enjoy the cultural diversity and creativity of Toronto, right on the water.

harbourfront center - places in toronto

Amsterdam BrewHouse

Located in the Harbourfront, Amsterdam BrewHouse specializes in offering patrons craft beers and delicious eats. Amsterdam BrewHouse’s ideal location makes it the perfect place to enjoy local craft beers, delicious local foods, and a lakeside view of Lake Ontario.

Visit my post called The Best Harbourfront Restaurant in Toronto to find out more about this awesome place!

Also, while at the Amsterdam BrewHouse I got to hang out with a good friend of mine and fellow travel blogger Danielle from the Thought Card. She’s a pro at cost effective travel so if you’re curious about budgeting a trip to Toronto she wrote a great post called Toronto Budget: How Much Does A Trip To Toronto Cost?  

amsterdam brewhouse - cool places in toronto
amsterdam brewhouse - cool places in toronto

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Walking the beat…

Even though I’m still discovering things in Toronto I know what to see and what shouldn’t be missed. This resulted in an itinerary with 50 things to see on each day. For the first couple of drafts, I needed to cut back, and when I did, it actually hurt my feelings. I had to pound the pavement and walk the 48 hour Toronto itinerary, in 48 hours to make sure everything was logistically sound. Living here gives me the privilege of seeing things when ever I want too. At the end of the day what ever I left out as well as some of the items in the itinerary will have their own individual post on the Toronto TravelIn My Own Backyard page.
toronto port lands - toronto itinerary
things to do in toronto - pinterest

Toronto Day Trips

Port Perry

If the hustle and bustle of Toronto is proving too much and you’re craving that small-town feel I strongly recommend Port Perry, Ontario. In about an hour’s time you can be sitting in the middle of a frozen lake (Lake Scugog) with friends, ice fishing, drinking beer and eating apple fritters the size of your head.

Often used as a filming location because of its small-town “American”, Port Perry’s historic downtown is one of York Durham’s prettiest little towns. With loads of boutique shops that line the Victorian streets starting from Lake Scugog with its Old Mill – Canada’s oldest grain elevator, up towards the Town Hall Theatre.  

toronto day trips - port perry
toronto day trips - port perry

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