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I think NYC, more specifically Manhattan, would be 1st in this category, hands down. After being a 16 year old with his permit driving through Times Square, driving has been a peice of cake for me. I drive like I've been doing it for 30 years because of NYC.
Not that I've physically driven in many other cities, but I would have to agree Manhattan is terrible... because of cabbies changing lanes with no warning (like signaling), the double-parked cars/trucks causing that, and worst of all... the pot-holes you MUST avoid all at the same time. You must've gotten a few honks at 16 & inexperienced though.
My first thought upon seeing the title was Boston. Reasons already well documented in this thread...
After some reflection, I'd also say LA is really tough if you don't have a good GPS that says street names. First time I drove there was in 2005 and GPS was not as common as it is now. With printed mapquest maps for every trip, it still took a driver and a navagator to get around the city for a week of business meetings. If you merge onto a freeway from the left, and have to exit in 2 miles on the right, that may sound simple, but in LA you need the full two miles to get over the 6+ lanes of traffic. And "turn right in 400 yards doesn't even begin to help you, when there may be 3 different exit ramps between 300-500 yards.
The traffic is horrible (took me longer to get from N LA to Manhattan Beach areas on the 405 than it did to get from Bakersfield to N. LA!!), but the real challenge in LA is knowing where you are going, what lane you need to be in, and which ramp to take, all with enough time to position yourself to actually do it.
In one week, we only missed one turn, but it took a lot of planning and communication....
Ah I don't know, but I tell ya Louisiana has the worst roads, highest car insurance, and the list goes on and on. Car company's send new model cars down here and test drive them a few months figuring if they can hanle these roads anywhere else will be a snap, many don't make it.
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