Which cities are toughest to drive in?

Good point. You have to be careful but. it can be done. Can't remember names/#'s but I messed up in Chicago my 2nd wk driving and was sitting in a mall parking lot trying to figure out what next when another driver came up to me. Asked where I was TRYING to go and directions. He laughed at the company directions and asked" do you want to get there the easy way or the best way?" WTF? He put me on wide 2 lanes and 4 lane expressways runing along the interstates and then a few diagnals that cut miles. Yes it was slow rolling like you said but was better than moving 2 ft every half hour. It pays to know There's more roads we can drive other than the big blue and green lines!

 

I hate NJ,DE,DC,MA,and....you guessed it, NYC and any place thereabouts. Got my 1st driver's award in NYC.
What about places that are labled Trk RT and even a GPS says you're ok and its got a 8'6 (I think that's right lol US 24/Broadway Lexington KY) overpass... I'm familiar with the area so I know better but a headache for sum1 that don't check the front of a map or read the 2 small signs. Older towns where 1 side of the overpass is 13'6+ and othe side is 12 or less. Think that's in Edenbourgh(sp)IN. Any TMC driver knows this 1 lumberyard/wood finishings.
Places with separate E/W or N/S streets/roads going in 1 way and finding a place to crossover to get where you need.
Detroit with all the 1 ways and service roads can be tricky for new drivers. Atlanta's not 2 bad if you time it right or go downtown call ahead 1st some places require a lot of backing, not room to turn around. Ouch I ranted too much. Look at any new place as a new experience, don't over think it, and just take your time.

 

While it is true most major cities can be a pain--and everyone has their personal favorite--or nightmare LOL--I surprised this thread has gone this long and no one mentioned New Orleans--that can be a real challenge-
Just my $.02

 

NYC isn't bad at all. I guess cutting your teeth in the NorthEast will do that to you. Philly, Boston, NYC, northern NJ, etc. nothing to be scared of. Just keep your eyes peeled and pay attention. You'll be fine. I did most of my driving in that area. Chicago does suck, but if you know where you are going, once again, not too bad. Los Angeles, I love LA. Even though you could be running two hours ahead of schedule 3 miles from your destination and still be 45 minutes late. But LA is an awesome city, along with the surrounding areas. I love driving the West Coast. Yeah, it's 55 in CA and OR, and 60 in WA, but I just sit back, relax and enjoy the scenery. Going balls out all the time gets old, and slowing down isn't bad.

 

Philadelphia

 

Joseph1135 no offense I cut my teeth in the NE and hated every mile. Did make cities everywhere else easier tho.

 

I second Philly there's a lot of low bridges.