No stranger to best places-to-go lists, Toronto is a friendly metropolis famed for its patchwork of neighbourhoods, diversity of food and culture, beloved sports teams and world class entertainment. The following itinerary features a mixture of the new, improved and classic experiences that Canada’s largest city has to offer. Of course, there’s no way to include all there is to see and do. so treat this as a guide and don’t be afraid to go rogue.  

Day One

Roy Thompson | Destination TorontoRoy Thompson | Destination TorontoCN TowerCourtesy of Destination Toronto

Ascend the CN Tower

Built in the 1970s and among the tallest free-standing structures in the world, Canada’s most iconic landmark, the CN Tower, offers fantastic views at dizzying heights.

Visit three hoods in a day

Eat your way through three neighbourhoods in a day each offering a different vibe, but all within easy walking distance of each other. No mandated order here, but perhaps coffee and a pastry at Wanda’s Pie in the Sky in Kensington, dim sum at King’s Noodles in China Town and a romantic dinner at Sotto Voce in Little Italy.

Kensington Market

Destination Toronto | Kensington Market Shopping in summerDestination Toronto | Kensington Market Shopping in summer

Following the tradition of the Jewish merchants who established this open-air market in the 1900s, vendors display their wares on the ground floors of colourful homes and on the sidewalks. Here, you’ll find everything from butchers, bakers and candle makers to gift boutiques, pot shops, gourmet eats, cheese and fish mongers, and vintage everything especially clothing and jewelry. Lots of patios for people-watching. Very 420-friendly.

China Town

Established in the late 1800’s, this vibrant neighbourhood bursts with Chinese, Vietnamese and Japanese restaurants and bakeries, unique shops packed to the rafters with various wares, sidewalk fruit markets and more. Art lovers will want to leave time to take in the Art Gallery of Ontario a few blocks east of Spadina on Dundas West.

Little Italy

little italy in torontoDestination Toronto

Strolling the streets of the first major little Italy in Toronto, you can still get a sense of what it must have been like in the 1950s when an influx of Italian immigrants began opening fruit stands, bakeries and other shops along College Street. Today, a myriad restaurants, bars and cafés create a culinary utopia. Those interested in pop culture and works by Toronto artists will enjoy swinging by The Local Gallery.


Take in some live music at the iconic El Mocambo (yep, the Rolling Stones have played here) or head to Queen West to the equally iconic Rex Hotel for live jazz and blues.


Day Two 

Take in Old Town and The Village

Destination Toronto | Toronto's Gooderham Building in Old TownDestination Toronto | Toronto's Gooderham Building in Old Town

The Flat Iron Building and St. James Cathedral are among the many 19th century buildings that dot the streets of historic TO. Enjoy the laid-back vibe of Old Town and the Distillery District, then head Toronto’s gay community for dins and a show.

St. Lawrence Market

St Lawrence MarketDestination Toronto

With well over 100 shops and a 200-year history, this landmark market offers something for every palette from a world famous peameal bacon sandwich to dozens of different types of mustard to fresh fruit and veggies, meats and cheeses, antipasto and more. Fabulous for a quick bite or take-back-to-the-hotel-room treats.

Museum of Illusions

Kids (and those who are young at heart) will marvel at this small fun-house museum where nothing is as it seems. Are you upside down in a streetcar? Are there multiple versions of you playing poker? Wait a minute, is that your head on a platter?

Distillery District

Madrina Bar y Tapas | Destination TorontoMadrina Bar y Tapas | Destination Toronto

Here, cafés, restaurants and shops are housed within a Victorian-era former distillery and easily accessible thanks to charming laneways and pedestrian-only brick-paved streets. Theatre and galleries add to the ambience and pubs such as Mill Street Brewery beckon visitors in for a pint.

The Village

The Village | Courtesy of Destination TorontoThe Village | Courtesy of Destination Toronto

Welcome to Canada’s largest 2SLGBTQ+ neighbourhood, Church Wellesley, also known as The Village. Here, famous hotspots like Woody’s and Sailor are nestled up to ice cream and pizza parlours, an iconic gay bookstore and drag show venues such as Crews & Tangos. To really experience the community, arrive in time for happy hour and perhaps a walking tour, followed up by dinner and a show.

Day Three

A bougie day of pampering and people-watching with a selection of museums in between.

Marvellous by Fred 

Indulge beneath an enormous chandelier at this Queen West patisserie where everything from the chocolate croissants to the little cakes are divine.

Little Canada 

Maya Masengi | Little Canada Maya Masengi | Little Canada 

Calling all giants (that’s you)! One of Canada’s newest museums exhibits miniature replicas of cities including Toronto, Niagara Falls and Quebec City with more representing the other provinces on the way. As day turns to night every 15 minutes, watch the lights come on in the cities presenting a whole new view of this animated and highly detailed world. Get yourself miniaturized and a wee you figurine will be permanently placed wherever you wish!

The ROM or Gardiner 

Royal Ontario Museum | Destination TorontoRoyal Ontario Museum | Destination Toronto

Destination Toronto | Totem Pole at the Royal Ontario MuseumDestination Toronto | Totem Pole at the Royal Ontario Museum

The Royal Ontario Museum (ROM) is Canada’s largest museum boasting 13 million artworks, cultural objects and specimens displayed within 40 gallery and exhibition spaces. The significantly smaller Gardiner Museum, situated across the street, specializes in ceramics and features 4,000 exhibits.


Sassafraz | Destination TorontoSassafraz | Destination Toronto

Spend the afternoon browsing and people-watching in Toronto’s esteemed Yorkville. Try the local hangout Hemingway’s or the upscale Sassafraz for lunch. If you’re in the mood for a facial, you’re in the right place with spas such as Rejuuv Medi offering fab treatments. Afterward, enjoy happy hour at the recently renovated Writers Room rooftop lounge at the Park Hyatt where city views are spectacular.

Catch a show

Destination TorontoDestination Toronto

Ballet, opera, theatre, the symphony ... with most shows starting around 8 p.m., you can sneak in an early dinner or lighter fare beforehand at one of the many restaurants in the Entertainment District (Melrose on Adelaide’s charcuterie board hits the spot for a pre-show nibble) or enjoy light fare and eccentric cocktails afterward at hotspots like Hartley’s or BarChef.

Sports enthusiasts may prefer to spend the evening taking in a game – Toronto fans are nutty about their baseball, basketball, hockey, football and soccer teams and there’s almost always a home game being played here.

Day 4

Destination TorontoDestination Toronto

Situated on the shores of Lake Ontario, Toronto surprises visitors with its vibrant harbourfront scene, waterfront trail and sandy beaches. Warm weather season extends from May to early October.

Pedal and Paddle

Grab a bike-share and pedal west along the waterfront trail to Budapest Park for a SUP or kayak lesson at Indigenous-owned Oceah Oceah.

Toronto Islands 

Destination TorontoDestination TorontoDestination TorontoDestination Toronto

A chain of islands connected by pathways and bridges and featuring massive green spaces, “the Island” is ideal for leisurely strolls, bike rides and picnics. Happily, it’s only a 13-minute ferry or water taxi ride away. Pop by the marina for lunch on a patio with Toronto skyline views or take the kids to Centreville amusement park.  There’s even a clothing-optional beach on Hanlan’s Point. 

Gone Sailing 

Be it a leisurely afternoon, Friday Night Wine & Cheese, Full Moon, or Sunset sail, there’s no better way to enjoy the harbour than cruising around on a fully crewed sailboat for a few hours. Public and private charters are available.

City Cruises 

Hop on board for an afternoon or evening on the water taking in the skyline, brunch or dinner, cocktails and on weekends, dancing on the upper deck to the tunes pumped on by the onboard DJ.

The Beaches (seasonal)

Destination TorontoDestination Toronto

Queen Street’s 501 streetcar transports beachgoers east to Toronto’s ultimate summer destination, The Beaches (aka “The Beach”), a vibrant neighbourhood chock full of restaurants and shops, with Kew and Woodbine beaches as a backdrop. Think boardwalks, sandcastles, volleyball, refreshments and all manner of water activities.

Queen Street 501

Bellwoods Brewery | Destination TorontoBellwoods Brewery | Destination Toronto

Alternatively, if you’re here in the off season or water is not your thing, the Queen Street 501 streetcar takes folks to Queen West and Queen West West, a haven of cool shops, bars and eateries. Stop by The Drake Hotel for a bevvy and a peak at local art;  Craft Ontario Shop which offer gorgeous one-of-a-kind pieces by Canadian craftspeople; and trendy Ossington Street for craft beer at Bellwoods Brewery or an evening sip of top shelf tequila at Reposado.

Looking for more local art and keepsake souvenirs? Visit 401 Richmond just south of Queen West near Spadina, a restored industrial building and cultural hub featuring galleries and boutiques such as Spacing which offers Toronto-centric books, games, apparel and accessories.

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