Filled with museums, stunning architecture, vibrant galleries, and design-forward restaurants, Toronto sets itself apart as a top culture destination and an unforgettable vacation for art aficionados. Discover how this diverse city offers an impressive array of sites and experiences for creative-minded travelers, whether you want to explore colorful street murals, learn about the history of footwear, or visit the largest museum in Canada—all while staying at The Drake Hotel, a boutique hotel with curated local art. This three-day itinerary makes the most of every moment for an inspiring Toronto getaway.
ItineraryPLAN YOUR TRIP
Day 1Welcome to Toronto
Kick off your trip at the Museum of Contemporary Art Toronto, a museum and art gallery that believes museums can be culturally and socially useful by fostering active dialogue and celebrating inclusiveness. MOCA’s current exhibition, Seeing the Invisible, incorporates augmented reality throughout some of Toronto’s public parks, guiding guests through virtual art and nature while addressing themes on the environment, sustainability, technology, and more.
Across town at the world-renowned Aga Khan Museum, North America’s first museum dedicated exclusively to Islamic arts, start with a feast of cantaloupe gazpacho, green harissa shrimp kebab, and eggplant stew with dill labneh at the onsite restaurant Diwan. Next, tour the jaw-dropping building, designed by Pritzker Prize-winning architect Fumihiko Maki, and its collection of ancient jewelry, textile, books, and artwork.
At dinner, Sofia in Yorkville will satisfy your eye as well as your palate. Admire an in-house gallery of international artists such as Banksy and Jean-Michel Basquiat while dining on seasonal Italian antipasti and pasta. Keep the party going with drinks at Cry Baby Gallery, a playful speakeasy that fuses street art and mixology.
Day 2Toronto’s Galleries and Street Art
In visionary Toronto, art doesn’t simply exist on white walls—it lives and breathes. Take a self-guided tour of Queen West Street, the epicenter of the downtown art scene, to find a fascinating mix of pop-up shops, indie boutiques, street art, and galleries. Pause for a postcard-worthy moment in Graffiti Alley, an ever-evolving, colorful tribute to the city, and with the iconic Giant Thimble sculpture that honors the factory workers who worked in this neighborhood when it was still Toronto’s garment district.
To see (and eat) edible art, head to Selva for dinner, a Michelin-recommended, multisensory restaurant that takes diners on a jungle-themed journey. Cap off your day by celebrating another facet of Toronto’s rich cultural milieu with an opera or ballet at the Four Seasons Centre for the Performing Arts.
Day 3Deeper into Toronto Art and History
Afterward, stop by two of Toronto’s cultural gems. Nearby Casa Loma, built by financier Sir Henry Pellatt in 1914 and one of Toronto’s most popular attractions, provides a glimpse into the city’s rich past. Its charming five acres of estate gardens are well worth a visit too. Nearby, Bata Shoe Museum serves as an international center for footwear research with an astounding display of more than 1,000 shoes and related artifacts, from Chinese bound-foot shoes to fashion-forward Manolo Blahniks.
Toast the end of an inspiring vacation back at Casa Loma’s BlueBlood Steakhouse, where you can enjoy caviar and dry-aged beef surrounded by heirloom antiques and modern art by the likes of Andy Warhol and Salvador Dalí.