Toronto Islands

The Best Places to Explore in Toronto with Friends

Published: May 28, 2024

Toronto, a city bustling with cultural diversity, vibrant neighbourhoods, and a variety of attractions, offers the perfect place to explore with friends. Whether you’re visiting for the weekend or a local, UP Express has you covered with some of the best options to explore when you’re hitting the city with your pals. Whether you’re looking for adventure, cultural enrichment, culinary delights or good old-fashioned fun, this city truly has it all. Join us as we uncover the best places to explore in Toronto and some ways to save big with PRESTO Perks while doing so!

If you’re visiting Toronto with friends and flying through Pearson Airport, UP Express has you covered with UP Group Pass. Groups of 3-5 friends can save up to 36% on one-way fares, so you can explore Toronto at a discount!

Explore the city with Simplii Financial and PRESTO! Earn a $250 PRESTO voucher‡ when you sign up for a Simplii FinancialTM Cash Back Visa* Card beginning May 14, 2024. Just add 2 pre-authorized payments of at least $50 for 3 straight months and the voucher’s yours. You can also enjoy cash back on eligible restaurant and bar purchases to make your adventures with friends even sweeter! ‡Conditions apply.

Head up the CN Tower

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First up, just steps from UP Union Station, is Toronto’s most iconic landmark: the CN Tower. If you haven’t been yet, this is a must-visit, especially with friends. Towering over the skyline at 1815 feet, this architectural marvel offers breathtaking panoramic views of the city and beyond. Ascend to the observation deck, where you and your friends can gaze over the cityscape and take in landmarks all over the city. For some adventure, dare to step onto the EdgeWalk, the world’s highest hands-free external walk on a building. Best of all, PRESTO Perks has you covered with 15% off General Admission Timed Tickets when you show your PRESTO card!

Go back in time at the Royal Ontario Museum

Exterior of the Royal Ontario Museum (ROM) in Toronto, ON.

Step into the past at ROM (Royal Ontario Museum), where art, culture, and nature come alive through captivating galleries and exhibitions. Featuring everything from contemporary art to ancient civilizations to natural history, ROM offers a journey through time for visitors of all ages. Explore the treasures of ancient Egypt, marvel at dinosaur fossils, and immerse yourself in the rich history of cultures from across the world. ROM is the perfect place to ignite curiosity and spark conversations among friends, and you can explore the 4.5 billion years of wonder. Another perk is that you can save 15% off regular admission rates with PRESTO Perks!

Go to a Sporting Event

Three people walking off UP Express train in Toronto Blue Jays jerseys

No matter the season, there’s always a sporting event to attend in Toronto! Catching a game with friends is the perfect way to spend a day in the city. Whether you’re a baseball, soccer or football fan, Toronto has a professional sports team for them all. If baseball is more your speed, a quick walk from UP Union Station, you can catch a Toronto Blue Jays game at the Rogers Centre.

Catch a soccer match at BMO Field and cheer on the Toronto FC. PRESTO Perks has got you covered with 20% off select Toronto FC home games for the 2024 season. If football is more your speed, catch the Toronto Argos at the BMO Field and save up to 20% off ticket prices to home games with PRESTO Perks. Get your friends together and experience all the excitement of sporting events in the city!

Get your Laugh on at a Comedy Show

Comedians on stage at The Second City

Laughter is the best medicine, and Toronto’s comedy scene delivers! Gather your friends and head to one of the city’s renowned comedy clubs for a night of laughs and fun. From established venues like Second City and Yuk Yuk’s to smaller indie comedy bars, such as Comedy Bar, Toronto offers a wide range of comedic talent to suit every taste. If you’re heading to Second City (a 10-minute walk from UP Union Station), be sure to take advantage of the PRESTO Perk available to save 20% off General Admission and Value Admission from Sunday – Thursday. So, sit back, relax, and laugh with your friends while you take in up-and-coming comedians and seasoned pros alike.

Day Trip to the Toronto Islands

View of the Toronto skyline from the Toronto Islands

Escape the hustle and bustle of the city with a day trip with friends to the Toronto Islands! Just a short ferry or water taxi away from downtown and within walking distance of UP Union Station, the island offers stunning views of the Toronto skyline. Spend the day exploring the island’s lush greenery, sandy beaches, and scenic walking and biking trails. Rent a kayak or paddleboard and explore the waters of Lake Ontario, or simply relax on the beach with a picnic and soak up the sun with your friends. Toronto Island offers the perfect day of relaxation away from downtown! If you’d prefer to stay in the city but still be close to the lake, we’ve got you covered with the top things to see and do on Toronto’s waterfront.

Indulge in the Food Scene

A bowl of poutine

Toronto is known for its culinary scene, which is as diverse as its population. So why not spend a day in the city (or better yet, an entire weekend) having foodie adventures with your friends? Embark on an adventure of all the best restaurants, food markets, and hidden gems. Start your foodie adventure off with the best burgers, ice cream, pizza, and croissants in the city! And if you’re thirsty, we’ve also covered you with the best local craft breweries in Toronto to check out across the city. Toronto truly has something to satisfy every budget and palate. Be sure to sample the local favourites, such as the peameal sandwich at St. Lawrence Market, butter tarts, and poutine! With a vibrant food scene, Toronto promises the perfect foodie adventure for you and your friends.

Get Artsy at the Museum of Contemporary Art Toronto (MOCA)

Outside of the Museum of Contemporary Art (MOCA) in Toronto, ON.

Immerse yourself in the world of contemporary art at the Museum of Contemporary Art Toronto (MOCA). Located in the heart of the city’s vibrant Junction neighbourhood and a quick walk from UP Bloor Station along the West Toronto Railpath, MOCA showcases cutting-edge works by both Canadian and international artists. Wander through thought-provoking exhibitions, interactive installations, and immersive multimedia experiences as you discover contemporary art trends and innovations. With its changing roster of exhibits and events, MOCA is the perfect adventure for art lovers. Spend an afternoon exploring the museum with your friends and prepare to be inspired by the sheer creativity.

Spend a day in the Junction

Outside of buildings in Junction neighbourhood in Toronto.

Next up, end your Toronto adventure with a leisurely day in the Junction, one of the city’s most eclectic and vibrant neighbourhoods. Located in Toronto’s west end and close to UP Bloor Station, this hip and happening area is home to an array of boutiques, galleries, cafés, and restaurants. Spend the day with friends strolling along Dundas Street West, browsing unique shops, and discovering local artisans. Stop in for a comforting brunch at Dirty Food Eatery, and then explore all the art galleries. We’ve got you covered with all the trendy things to do in the Junction neighbourhood. As evening falls, be sure to check out the literary cocktail bar, Famous Last Words or one of the many breweries. With its laid-back vibe and lively atmosphere, the Junction is the perfect spot to get out of the city's heart and explore with friends!

Toronto is the perfect city to explore with friends and create unforgettable memories! The city has something to offer everyone, from iconic landmarks to cultural experiences, culinary delights, and vibrant neighbourhoods. Also, keep in mind that PRESTO Perks offers discounts for many attractions across the city, so check it out before planning your day. So, grab your pals, hit the streets, and prepare for your Toronto adventures!