How to Spend the Best Three Days in Toronto with UP Express!
Published: July 25, 2024
From trendy bars to some of the best food you'll try in your life, Toronto is consistently rated as one of the best tourist destinations in the world year after year. And with Canada's largest airport, Toronto Pearson International Airport, and UP Express, getting here has never been more accessible.
If you're a first-time visitor or returning to this vibrant city, this itinerary will help you make the most of your time in Toronto using UP Express. From iconic landmarks to hidden gems, get ready to experience the best of what Toronto offers. After three days, you'll be begging to come back!
So sit back, relax, and let UP Express take the guesswork out of planning your long weekend or mid-week getaway in the city!
Day 0: Arrival and Toronto by Night
Arrive in Toronto and transfer to UP Express
Arriving on one of the countless direct flights from around the world to Toronto Pearson International Airport?
Welcome to Toronto!
Collect your bags, clear customs, and follow the signs for "Train to City." Need to find your way to UP Express? Watch our step-by-step videos to help you find your way from Pearson Airport Arrivals to the UP Express platform. UP Express began operations in June 2015 and is North America's first dedicated air-rail link. Tap on your debit card, credit card, or mobile wallet on phone or watch on the UP Express PRESTO machines or purchase a ticket online before boarding, and don't forget to tap off when you get off the train before leaving the station. Be prepared to pass under, over, and through Toronto's suburbs as you are whisked to Toronto's downtown transit hub, Union Station, in just 25 minutes.
Be sure to check schedules before you arrive. The first train departs UP Pearson Station at 5:27 AM on weekdays and 6:27 AM on weekends and runs until 12:57 AM. With trains running every 15 minutes, you won’t have to wait long until you arrive in downtown Toronto.
Check into one of Toronto's best hotels
Whether looking for contemporary luxury, rooftop pools, or something more unique and local, Toronto has a hotel for everyone. Check out our Discover Toronto blog, Best Places to Stay in Toronto.
After arriving at Union Station, connect to the TTC or walk to your hotel.
Dinner and Drinks near Yonge and Dundas to soak up Toronto's Times Square at night
Walk or take the subway to Dundas Station and soak up the energy of Yonge and Dundas Square. Head to one of the many restaurants nearby for a delicious dinner. Enjoy the vibrant atmosphere and the dazzling lights that make it feel like Canada's Times Square. Plenty of options exist for every palate, from trendy restaurants to international cuisines. After dinner, experience the lively nightlife with a visit to one of the area's bustling bars or lounges for drinks and entertainment.
But don't stay up too late; you have a busy weekend ahead of you!
Day #1: Toronto, the old
Morning:
Start your day with a walk or streetcar to St. Lawrence Market, where you can enjoy a coffee and breakfast. Be sure to check out the world-famous peameal bacon, or, as we call it in Canada, the "Canadian Bacon" sandwich.
Coffee in hand, continue your walk to the Distillery District. The area is renowned for its charming cobblestone streets, historic buildings, and vibrant arts scene. With numerous art galleries, boutiques, and artisan shops, the district offers a unique shopping experience. Going in the morning will avoid the crowds that flock to the area in the afternoon.
When you are done exploring, catch the iconic Toronto 504 streetcar towards downtown.
Afternoon:
Get off the streetcar near John Street and walk towards the iconic CN Tower.
As one of the tallest freestanding structures globally, the CN Tower guarantees an unforgettable experience for those visiting for the first time, including the chance to step onto the Glass Floor and Outdoor SkyTerrace, adding an exhilarating twist to your visit. However, if you aren't interested in going all the way up, snapping a quick picture at the bottom is a must for those interested in Toronto-made artist Drake, who used the iconic tower as a backdrop for his album "Views."
At the bottom of the tower, you'll find the historic Roundhouse Park. Catch a Blue Jays game and a hot dog at Rogers Centre if time permits. If no game is happening, stop by Steam Whistle Brewery for a snack and drink on one of the best patios in the city.
After a quick break, walk along Northern Linear Park towards Fort York Historical Village. Fort York Historical Village in Toronto holds immense historical significance as it was a crucial military fortification during the War of 1812. Its history matters because it played a pivotal role in shaping the development of Toronto and Canada as a whole. Visiting Fort York Historical Village provides a glimpse into the past, allowing visitors to appreciate the challenges and triumphs that have contributed to the city's rich heritage.
Evening:
After walking, rest those weak legs at a local watering hole at Stackt Market, a new contemporary brewery and snack spot near Fort York Historical Village. You'll be well-positioned to return to your hotel before dinner or go out for dinner from here.
Considering we went out the night before, keep it chill and head to Toronto's newest food hall, the Wellington Food Market at The Well.
The Well is Toronto's newest boutique entertainment space and has introduced many exciting new food options, catering to diverse tastes and preferences. Whether you're in the mood for gourmet burgers, artisanal pizzas, or international cuisine, The Well has something for everyone. With a vibrant food hall offering a variety of culinary delights, along with trendy cafes and upscale dining establishments, The Well has become a hotspot for food enthusiasts looking to indulge in a delightful dining experience in Toronto.
Continue the night along Queen Street West, one of Toronto's trendiest neighbourhoods. Along this stretch of Queen Street, you will encounter some of Toronto's Best Bars for those looking to stretch the night!
Day #2: Toronto, today
Morning:
After some beauty sleep, slowly walk or take the subway to Nathan Phillips Square at Queen Subway station. Here you will see our new City Hall. Grab a picture at the iconic Toronto sign. City Hall and Nathan Phillips Square embody the future of Toronto, with ample space for community organizing, standing starkly to Old City Hall across the street.
Next, walk west towards Kensington Market. Why not try Jimmy's Coffee at McCaul and Baldwin Street? Jimmy's Café is one of Toronto's Best Cafes and a great spot to try this Toronto-exclusive coffee.
Kensington Market is significant for its vibrant and diverse community, which makes it a melting pot of different cultures and backgrounds. The area is celebrated for its rich history, eclectic mix of shops, and diverse culinary offerings, which reflect the city's multiculturalism. The market has become a symbol of Toronto's inclusive and accepting nature.
Those looking for a challenge should try one of Toronto's famous Jamaican Patties. Small and ready to move, these are a staple in a city as fast-moving as Toronto because of their easy portability.
After walking west, stop for Dim Sum at Toronto's world-famous Chinatown on Spadina. Known for its rich cultural heritage and authentic Chinese cuisine, be sure to try the delicious soup dumplings, also known as xiaolongbao. The area is filled with bustling markets, traditional architecture, and a wide range of shops and restaurants offering a genuine taste of Chinese culture.
Afternoon:
After brunch, take the 510 Spadina streetcar to the University of Toronto (Harbord and Spadina).
The University of Toronto, founded in 1827, has a rich history and is known for its excellent academic programs and diverse student population. One of the best ways to explore the university campus is by leisurely walking through its historic grounds and beautiful architecture. Stroll through the Philosopher's Walk to experience the serene landscape and the stunning buildings of the Faculty of Law and Trinity College.
We're slowing it down now with an afternoon at the museum! Several museums near Queen's Park offer a fascinating glimpse into art, culture, and history. The Royal Ontario Museum stands out with its extensive collections of natural history, art, and world cultures. Just a short stroll away, the Gardiner Museum showcases a remarkable collection of ceramic art worldwide. Meanwhile, the Bata Shoe Museum offers a unique perspective on footwear's history, culture, and design.
Evening:
It's time to get fancy!
Grab the TTC line 2 subway from your hotel or Queens Park to the Danforth neighbourhood.
The Danforth, also known as Greektown, is a vibrant neighbourhood in Toronto known for its diverse selection of restaurants. After dinner, walk towards Riverdale Park to experience the best skyline sunset in the city. Pose for a picture before catching the TTC line 2 subway back towards Bloor and Yonge.
Yorkville is a historic and upscale neighbourhood in Toronto known for its charming streets, high-end boutiques, and vibrant celebrity scene. It was once a hippie haven and a bohemian enclave in the 1960s and has since transformed into a luxurious and trendy area. The Writers Room Bar, located in the heart of Yorkville, is a sophisticated and elegant establishment known for its inspired cocktails and cozy atmosphere. The Writers Room Bar is one of Toronto's Best Bars and features another skyline view, this time of all the glimmering lights leading you back towards downtown and your hotel.
Day #3: Break from the city with Toronto's nature!
Morning:
(If you can) wake up early and make your way toward the Toronto Island ferry at Jack Layton Ferry Terminal. It is best to go early to avoid crowds looking to spend the day at Toronto's best park!
The Toronto Islands are a charming and picturesque escape from the bustling city life of Toronto. Accessible by a short ferry ride and free of all cars, the islands offer stunning views of the Toronto skyline, beautiful beaches, and peaceful natural surroundings. Visitors can enjoy various outdoor activities such as biking, picnicking, and kayaking, making it an ideal destination for nature lovers and families.
Challenge yourself to walk to Hanlan's Point, a famous LGBTQ+ historical space, before grabbing the ferry back to downtown Toronto.
Afternoon:
If time permits, do as the locals do and enjoy one of Toronto's many breweries!
Visiting the breweries in Toronto during the summer is a fantastic way to experience the city's vibrant culture while enjoying refreshing and locally crafted beers. Many breweries offer outdoor patios and beer gardens, creating a perfect setting to socialize with friends while savouring delicious beverages in the warm weather.
Trinity Bellwood's Park is often packed with people enjoying the sun with a cold drink in their hands. Venturing further west, stop by Henderson's, Bandit, or Wallace for a quick drink. Feeling adventurous? Go for a walk and try them all!
Looking for a list? Check out Discover Toronto's blog: 12 Must-Visit Local Craft Breweries.
Evening:
Depending on your flight time, catch the TTC 505 Dundas streetcar to Dundas West. There, an air-conditioned, comfortable, and Wi-Fi-connected UP Express train will whisk you back to Pearson Airport without the stress!
Toronto is a city you have to visit again!
Whew! That was a packed three days!
But guess what? We barely scratched the surface of all that Toronto offers. The good news is that Toronto Pearson International Airport provides excellent connections to the rest of the world, with many direct flights around Canada, the United States, and Europe, making it easy to return and explore more.
Plus, when you come back, we at UP Express will be waiting to whisk you from Pearson Airport to the heart of the city, ready to show you around again. Toronto's diverse neighbourhoods, rich cultural tapestry, and exciting events ensure that there's always something new to experience.
So, until next time, happy exploring!