http://maps.google.co.uk/maps?q=edinbur ... 6&t=m&z=15
Edinburgh can be quite interesting because you've got the Old Town near the castle, south and east of Princes St Gardens on this map, dominated by a single long street with lots of little spines coming out from it like a backbone, and lots of windy streets and alleyways going up and down and over each other, and the painfully grid-structured Georgian New Town (built in the 18th century, so not very new anymore) to the north of the Gardens.
The rest is pretty fucking chaotic, though. There's elements of a grid structure near where I live, but it fits inbetween routes that I suspect are much older and follow a more-or-less straight-but-a-bit-bendy route from the centre of town. If you go down to the docks at Leith, which used to be a separate city that was subsumed quite a long time ago, it can be very easy to get lost if you don't know what you're doing because the roads just go wherever the hell they like, but getting there is very easy as you just go down a very straight long road.http://maps.google.co.uk/maps?q=york&hl ... 6&t=m&z=15
York on the other hand, which is the only other city I've spent a reasonable length of time in, has windy, bendy, narrow streets as the norm, including a giant pedestrian zone in the centre. Grid-system-like structures just don't exist to the same degree (there are a few, but they're more difficult to discern on the map), even in the more newly developed areas outside the city centre (which is conveniently marked by an orange ring road on the google map), although they are much newer than the Georgian bits of Edinburgh. Houses are much more tightly packed together than in Edinburgh, however; in York the norm is terraced houses with a small yard out the back, while in Edinburgh the norm, especially in the Georgian and Victorian areas, is terraced 3 or 4 storey apartments with a large shared garden. So in York, instead of grids, you often see rows of streets very close together, and you also get alleyways that are marked as roads on the Google map. It's also common to find houses on a small cul-de-sac away from the main road, at least to a greater extent than Edinburgh (I shouldn't talk, I live on such a cul-de-sac here...).
Also, I'm not sure, but I get the distinct feeling that I found it more infuriating to try and get places in York, because side streets are more likely to be dead ends that don't lead anywhere. In Edinburgh I can usually just point myself in the rough direction and start walking, particularly in the Old Town, and alleyways will usually come out where I want them to, or else it's on a (pseudo-)grid system. York often had me take a long way round a certain piece of land that didn't have any paths running through it. I do get that a bit in Edinburgh too, to be fair, like near my house there's a railway line and I have to go to a bridge (fortunately I live near such a bridge and it's usually not a problem, but if I'm coming from the other direction it can be annoying). One particularly annoying example from York is shown below: I lived at the red dot and wanted to get to the supermarket at the blue dot. But I couldn't just walk off the north end of the university campus because there was a fence. So I had to go round via the green routes (both of which took roughly the same amount of time). Agh!
Also, it took me the best part of a year to get used to the layout of York's town centre, and I was still discovering things years later. Just sayin'.