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I Got Hometown Advantage. The 48 Hours Toronto Itinerary – Tried, Tested & True 

Day 1

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.

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”.

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 a natural water called Taddle Creek, which was buried during the industrial age and now flows underwater.

Taddle Creek

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.

Baldwin Street, Restaurants (*Hidden Gem)

This small Toronto enclave is located in Toronto’s Grange Park neighborhood. Baldwin Village is famous for its small shops and restaurants like, Shawarma and Falafel Place, Chardise, Sid’s Deli, and many other favorited restaurants of Toronto. 

Kensington Market

Kensington Market is Toronto’s self-proclaimed “most vibrant and diverse neighbourhood”.  This bustling Toronto neighborhood 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”.

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.

Queen Street West

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

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 kilometer (.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

Rogers Centre (a.k.a. The Sky Dome)

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).

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!

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.

Day 2


We loved using Airbnb so much we started our own. Located in the core of Toronto’s thriving Entertainment District, your room will offer you a true lifestyle experience with a neighbourhood feel.

Coming To Toronto? Stay with us.

Booking Flights:


The average person doesn’t need to think twice about getting out of town for a 48 hour travel adventure or a long weekend. The only thing stopping you dead in your tracks is finding cheap flights. Please visit our helpful posts on Booking Flights. Personally, I’m all about simplicity so I recommend Skyscanner, the the best way to search the best rates in flights.


This was actually tougher than I thought. In a way, it’s sort of like reverse engineering. You see, when I’m traveling abroad, I follow a two-day itinerary I created after days and months of research. Sometimes you discover things you didn’t plan for or miss things that would have been amazing to experience. It’s a gamble. I get it and I know I’m not going to see everything a city has to offer in 2 days.

Creating a Toronto itinerary was different. It was difficult because I know this city. I was born, raised, live and work in this city.


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 hurt my feelings to have to leave things out. I had to pound the pavement and walk the 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 Travel – In My Own Backyard page.

About Me:
Using the latest travel apps, technology, and gear, I take a city; see the sights, taste the food, smell the roses, hear the stories and feel the love. All in 48 hours. Then, using videography & editing, photography and writing I retell and share those stories with my readers and viewers.

I'm Christopher Rudder and welcome to Rudderless Travel.

Read more about me here: Being Rudderless With Christopher Rudder and here: Rudderless Travel gets nominated for the Leibster Award.

This blog uses affiliate links at no extra cost to you. We also accept sponsored posts but only if we feel the brand, product or service is a perfect fit with who we are or what we post..
All opinions belong solely to the blog unless otherwise mentioned and never influenced by a third party ’cause that's how we fly.


Day Two:

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, theaters, and more!

Mill Street Brewery Situated in Toronto’s Distillery District, Mill Street Brewery is a community- friendly brewery that prides itself on its humble beginnings. Since 2002, Mill Street Brewery has expanded twice (once in 2006, then in 2012). Aside from its humble beginnings, the folks over at Mill Street Brewery have an “earth-friendly” philosophy when it comes to brewing beer, with their Original Organic Lager, which was the breweries’ first beer ever made, and the first organic beer to be brewed in Ontario. Mill Street Brewery’s eclectic portfolio boasts over 60 unique beers that have won have won over 100 awards, including 3-time Canadian Brewery of the Year.

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 provides 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 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. Gooderham  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 an historical landmark that adds to Toronto’s pizzazz.   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 meter (305 foot) tower and pointed spire. Metropolitan United Church Metropolitan United is the largest church in downtown Toronto. Located at 56 Queen St E, this non-dominational church welcomes people of “any faith or orientation” into its community. The Metropolitan United Church is a progressive church that is outspoken on social issues and is whole-heartedly committed to strengthening the community through faith and worship. Yonge-Dundas Square Yonge-Dundas Square is Toronto’s equivalent to 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. 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. Old City Hall Old City Hall is Toronto’s 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. 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 are stand at varying heights. Toronto City Hall’s courtyard, Nathan Phillips Square, serves as the primary host of various festivals and events in Toronto. Yonge St. Centered 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. 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. Toronto Islands This small chain of islands in Lake Ontario is just south of mainland Toronto. The islands offer visitors an array of fun and engaging activities and events to do. The Toronto Islands is comprised of six different islands, with beaches, amusement parks, ferry boats, live concerts, yacht clubs and many other fun activities for visitors of all ages. Gibraltar Point Lighthouse The Gibraltar Point Lighthouse is a stone lighthouse that has been standing on the Toronto Islands for the past 300+ years. Despite being occasionally open for tours, the Gibraltar Point Lighthouse has been decommissioned since 1956. It is common folk lore that the lighthouse is haunted by the ghost of its first keeper John Paul Radelmüller, who was murdered by drunken soldiers in 1815. Harbourfront | Harbour Centre The Harbourfront Centre is nonprofit cultural organizations that puts 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. 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. King West Village Kings West Village is one of Toronto’s fastest growing communities. With waves of young professionals moving into the neighborhood, 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.

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