Start: College Station, and a streetcar west to Augusta Avenue.
1. Kensington Market
A bustling street market of fishmongers, vintage retailers, coffee shops, and music stores, Kensington Market pulses to its own beat. It's a multiethnic mélange that was once a Jewish neighborhood — the original synagogue still remains — and has been gradually layered with successive waves of immigrants from Portugal, the Caribbean, and the Middle East. If you want to bring home great vintage finds, do some shopping in this area (check out Tom's Place, Fresh Baked Goods, and Courage My Love). Life starts later in the morning here and stays up well into the night.
2. La Tortilleria
On the edge of the market is this tiny spot comprising just a few stools inside and, weather permitting, tables out front, that serves good corn tortillas made daily. Tacos and bottled drinks from Mexico round out the tiny menu. There are other locations around town, some of them supplying Mexican groceries, as well.
Toronto has a large Chinese population dispersed throughout the city, but this was home to the first great wave of Chinese immigrants. It's changed since its early days, particularly because of the infusion of Hong Kong money. It's such a large and significant area that it's a shame no official entryway exists. The addition of gilded statues of dragons and the like on poles in the middle of Spadina Avenue is a nice touch, however.
4. Art Gallery of Ontario
With renovations completed in 2008 — by local boy Frank Gehry, who grew up around the corner — and now blessed with the brilliant Thomson Collection, the AGO is arguably Toronto's best gallery. Visit for the stellar collection of paintings by Canadian legends and European masters, the best collection of Henry Moore sculpture in the world, the photography gallery, and much more. Stop at the low-key cafe for a quick lunch.
5. Sharp Centre for Design
Although Toronto has long suffered an out-of-date reputation for being straitlaced, when people do wacky things here, the new additions are quickly absorbed into the accepted cityscape. This brilliant bit of design from Will Alsop is a cube on stilts that requires a first-hand view to really appreciate its beauty. It's home to the Ontario College of Art and Design (OCAD) and is closed to the public except on special occasions, such as an annual art fair.
6. Queen Street West
Once considered the edge of the city's hipsterdom, this strip is now a mix of chains such as The Gap and enduringly cool boutiques (Fashion Crimes, Peach Berserk, and the like). It's still a great place to park at a cafe, bar, or pub, and watch the parade go by — there's always plenty of street life to take in.
7. The Art & Design District
This is one of Toronto's most interesting neighborhoods. Still a bit gritty in spots (which means it hasn't been sanitized), it's filled with exceptional, small-scale art galleries and independent boutiques run by local designers. Mid- to late afternoon is the perfect time to check it out because everything is open (some of the shops are closed all morning) and the streets are full of life. Great restaurants with lively patios and some exciting live-music spots make it an appealing destination after dark, as well.
8. Trinity Bellwoods
This site used to be the home of the precursor to the University of Toronto. The buildings have been torn down, but the impressive stone-and-wrought-iron gates that face Queen Street West still remain, and there are Victorian lampposts along the main paths. There are benches where you can rest and take in the scene, but it's more fun to wander. As you do, watch out for the legendary albino squirrels who reside in the park.
9. Oyster Boy
Torontonians love oysters and other seafood, and this is one of the city's seafood institutions. It's known for its exceptionally fresh oysters, an excellent selection chosen by owner Adam Colquhoun, and a friendly pub-like atmosphere. The fish-and-chips are great, too.
10. Museum of Contemporary Canadian Art
You've already seen the iconic art of the AGO; now's your chance to see what's happening in today's art scene. MOCCA is a gallery that has a reputation for its (sometimes freaky) temporary exhibits. Edgy, good stuff.
11. Ossington Avenue
For years, this has been a sleepy part of town, part of Toronto's Little Portugal neighborhood, where many of the houses have religious icons painted near the front door. But now, Ossington Avenue is the epicenter of Toronto nightlife. Drop in at Watusi for 1960s retro-cool cocktails and ambience, or at Sweaty Betty's for a no-fuss vibe and a great patio.