Back in the 1960's, Yorkville was Canada's answer to Haight-Ashbury, a bohemian enclave home to then subversive personalities like Neil Young, Joni Mitchell and Margaret Atwood. Much has changed in 40 years and while those same people probably like to pop in to their old 'hood when they're in town, there's little left of its peacenik past.

In the decades since, Yorkville has mutated into one of North America's most expensive neighbourhoods and Toronto's playground for the rich and famous. You'll still stumble on the occasional eccentric on Yorkville Avenue, but these days they're more likely to be a silver haired fox wearing a $150 pair of bicycle shorts and smoking a Cohiba Esplendido.

That said, it's still one of the city's premier tourist destinations and one of the best spots in town for an afternoon of people watching (that bicycle short wearing, cigar smoking guy is real). The trick is to find the right vantage point and Ciao Wine Bar has just the patio. Well, they have two actually; one street-side and another along a pedestrian corridor, both prime for people watching.

Who goes there?
During my short visit I encountered a lot of silver hair, expensive suits and very, very tanned skin, but to my surprise--virtually no arrogance. The maĂŽtre d' was incredibly friendly and helpful and didn't mind at all that a scruffy red head in faded jeans and a worn, army green jacket was loose on the premises. It's rare that I get the opportunity to bump elbows with the Ferrari crowd, and I realized I'm far too quick to judge.

Grub and Libations
Ciao Wine Bar specializes in - duh - wine; particularly of the Italian variety although you'll find a humble selection of new world wines from Canada, the U.S., Australia and New Zealand. The selection from Italy is divided by region representing the entire peninsula. You can fetch a glass for as little as $10 and bottles range from $40 to just about as expensive as you'd like to shell out.

The menu is a pretty standard contemporary Italian card featuring a selection of antipasto ($8-15), fresh pasta ($16-19) and pizza ($10-20) among other things. Every Tuesday they offer linguini with a fresh whole lobster for $21, which sounds pretty reasonable to me.

Odds of scoring (a seat)
Every patio in Yorkville becomes sought after real estate when the sun is shining, and Ciao is no different. They do take reservations though, so if you've got someone to impress it's probably best to call ahead.

A view to a ...
As I mentioned before, this is prime people watching territory. Because of the neighbourhood's weird and wonderful history there is this totally unique blend of people within Yorkville's invisible walls. It's a mix of meandering tourists, lunching ladies, sports cars, kids drunk on entitlement, George Hamilton lookalikes, rich aging hippies--oh, and so much cigar smoke. There is nowhere in Toronto - nowhere - that loves cigars as much as old men in Yorkville loves cigars. In a mere half hour my sightings hit double digits, they're everywhere.

SPF recommended
The neighbourhood is pretty dense, so its not the best place to sunbath, a bit ironic considering the saturation of tanned skin. Still, the rays to peak through. Both patios at Ciao are protected by retractable awnings though, obviously mainly for rain, but it's good to know that if summertime gets a little too intense, us scruffy redheads are safe.

Overall Impressions
To me, Yorkville is one of those places where I feel like a tourist in my own city. It's a great place to visit, but I wouldn't want to live there. However, when I do visit I think I'd like to have a drink on the Ciao patio. It embodies modern Yorkville in all the right ways. It feels swanky and sophisticated, but still accessible (and you're treated that way, even if you're not dressed that way). It's a place for legitimate tourists, those like me and regulars alike--maybe even the cigar smoking cyclist.

Previously in the series:

• House on Parliament
• Three Speed
• href="http://www.blogto.com/eat_drink/2011/05/toronto_patio_season_preview_pour_boy/">Pour Boy
• Markaz Cafe
• Churchill
• Jason George
• Town Crier
• O&B Canteen
• Stout Irish Pub
• The Blake House
• Origin
• The Caledonian
• Marben

A special thanks to Rickard's White for sponsoring our patio adventures.