Boston, without a doubt. I've driven (not anything larger than a 1-ton pickup) through a lot of cities in the US.

Boston is the worst. In the core of Boston, it is an old city, without enough room, lots of one-way streets, hills, and "bent" streets. I don't think there is one straight and true street in all of Boston. Streets run at crazy angles to the compass... and then we have to talk about Boston drivers.

Boston drivers consider using their turn signals to be "giving information to the enemy." So they don't use turn signals.

Then we get to the roundabouts as you get outside the core of Boston.

If I never drive in Boston again, I will consider my life better lived.