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There's one problem with vacations – they end. This can be tough, especially for a car buff who spends time in a road paradise, then returns to Toronto (also known as the lowest circle of driving hell).

My wife and I recently came back from two weeks at Lookout Mountain, home to some of the finest roads in North America. Set in the green hills outside Chattanooga, Tenn., Lookout is a place where three cars is considered a traffic jam, and a road never goes more than a few metres without an interesting curve. We spent our days gliding through country vistas, parking for free, and ripping through mountain switchbacks in our little red sports car.

After this, returning to Toronto was not unlike being sent back to federal penitentiary after a parole revocation. We were back to the home of the traffic jam, the $6,000 insurance bill and some of North America's worst roads.

Like the original blues – a musical form rooted in suffering – driving in Toronto has a cultural history that only its beaten-down members can understand.

Here is a list of the Top 10 reasons why Toronto is the Mississippi Delta of driving:

Construction: I moved to Toronto in 1984. The Gardiner Expressway was under construction that year. Thirty years later, it still is.

Costs: High costs are a way of life, perhaps even a religion. Like prisoners whose will has been destroyed by years of torture and deprivation, the long-time Torontonian takes a hosing without complaint – we come to believe that insurance costs and a $1.2-million house with bad wiring, faulty plumbing and leaking basement are normal. Our friends down south added some perspective. When I told them what fuel costs – about 30 per cent more than it does in Chattanooga – they were astounded. Then I told them about license renewal fees and the cost of parking in downtown Toronto. No one plans on moving here any time soon.

Street cars: I love the ambiance of Toronto's streetcars. In an ideal world, they would run on dedicated lanes. Instead, they share streets with cars and this creates a set of built-in problems. Drivers zoom past the streetcars, unaware that they are about to disgorge passengers (disembarking from a Toronto streetcar can make you feel like a pin in a bowling alley). But the biggest problem is rooted in materials engineering – since steel and concrete expand at different rates, the tracks destroy the roads with clockwork regularity. Then come the construction crews. For a few months, the tracks and the street around it are smooth as a billiard table. Then the first cracks appear, followed by gaping holes, wheel-busting ridges and construction crews. It's a life sentence, without parole.

Traffic: In the rural south, a 30-minute trip takes 30 minutes. In Toronto, you should allow two hours. Unless there's construction which might turn it into three hours. Or five. Bring something to read.

Parking: During two weeks in the south, we spent a grand total of $1.50 on parking. On our first day back , we spent $14, and considered ourselves lucky – at least we found a spot.

Midnight auto supply: Toronto is home to one of the world's great urban cultures. We like that. Unfortunately, this culture seems to include a disproportionate number of thieves and vandals. The badges on our Honda, which are apparently prized by some gang that I'd never heard of before, were stolen while were away. Although I may have lost count, I believe this is the fourth time. We've decided that the car looks cooler without badges.

Road cuts: The repaving of a street is followed immediately by the arrival of construction crews that cut the new pavement to repair something – it could be a gas pipe, a water main, an electrical vault … the list of tasks is apparently endless. It would make sense to do these things before the road is repaved. Instead, the new pavement is patched, re-patched, then patched again. A couple of years later, they tear it all out and repave. And a few days later, a crew arrives with a concrete saw to start cutting. For Toronto road contractors, this is the Great Circle of Life.

Skill levels: There are several million people in the GTA. Their driving skills vary considerably. Although this is true of other jurisdictions as well, it has a bigger impact in a place where you're packed in like sardines, and the roads are being cut apart every day for repairs.

Potholes: Toronto can't help that it's situated in a climatological region noted for multiple thaw and freeze cycles that create the perfect conditions for potholes. But this won't make you feel better when you rip the wheel off your new sports car.

Grid layout: If you love to drive, there's nothing better than curving roads that let you explore your car's handling. Arcing through a constant-radius curve and feeling the grip of your tires through the steering wheel makes you feel alive. Unfortunately, Toronto's roads were designed by a traffic bureaucrat whose tools were limited to a lead pencil, a straightedge ruler and a 90-degree angle. There are about half a dozen curves in the entire city. But don't get too excited – they're under construction.

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