3-Day Toronto Itinerary: Museums, Galleries, and Theaters

A long weekend in Toronto will give you time to enjoy the city’s museums, galleries, and theaters. Base yourself at the arty Drake or Gladstone Hotels, or choose a lodging in the Entertainment District, like the Hotel Le Germain, Soho Metropolitan, or Thompson Toronto. Plan a day trip to see a show in either Stratford or Niagara-on-the-Lake.

street in toronto distillery district
Toronto’s Distillery District. Photo © Carolyn B. Heller.

Day 1: Art Galleries and a Night at the Theater

Start your museum meandering at the Art Gallery of Ontario, which has an extensive collection of Canadian and international art in a striking building designed by Frank Gehry. Next door, you can’t help but notice the Sharp Centre for Designit’s the checkered box floating in the sky supported by yellow, blue, and purple “pencils.”

Head east to the Distillery District to browse more galleries, including the Artscape Building, which houses more than 60 artist studios. After lunch in one of the district’s cafés, go downtown to see what’s happening at the always-bustling Harbourfront Centre. Check out the Power Plant Gallery, and watch the artists at work in The Craft Studio.

Have dinner in the Entertainment District, then catch a concert at Roy Thompson Hall, a performance of the National Ballet of Canada, or a play at one of the city’s many theaters.

glittery platform shoes worn by elton john
Elton John’s platform shoes on display at the Bata Shoe Museum. Photo © Carolyn B. Heller.

Day 2: Museums and Film

A tour of the Elgin and Winter Garden Theatre Centre takes you through Toronto stage history in Canada’s only “double-decker” theater. Then get a dose of world culture and natural history at the Royal Ontario Museum. Nearby is the eclectic Bata Shoe Museum, which houses more than 10,000 shoes—from doll-like slippers worn by Chinese women with bound feet to singer Elton John’s sky-high platforms.

Make an excursion to the Junction Triangle to see what’s on at the Museum of Contemporary Art, then take a break at one of the neighborhood’s craft breweries. Your next stop is Queen Street West, where you can wander into whichever galleries and boutiques catch your eye and where you have lots of options for a meal. After dinner, see what’s screening at the TIFF Bell Lightbox.

Day 3: Theater Day Trip

From Toronto, it’s an easy day trip to either the Shaw Festival Theatre in Niagara-on-the-Lake or the Stratford Festival in Stratford. Take a behind-the-scenes tour of the theater before lunch, then see an afternoon matinee. You’ll be back in Toronto in time for a nightcap to top off your weekend of art and culture.


Related Travel Guide


Pin it for Later

toronto itinerary pinterest graphic