The two cities I bike in the most are Boston and NYC. Though they share some similarities they are quite different. I find getting around NYC and Brooklyn a bit more fun than Boston. The infrastructure connects better and, if I plan my route well and take my time- not push too fast a pace, I can have an enjoyable safe ride to just about anywhere.
In Boston the infrastructure is more spotty, the drivers are abysmal- rude, impatient, territorial and aggressive and I often feel myself pushing the pace to stay with traffic. NYC seems to prefer a steadier pace for me. Too fast in NYC is asking for an accident.
I'm also a road rider and bike tourist and do a lot of riding far from cities. That is also a completely different style and set of expectations.
I've ridden in a lot of US and Canadian cities, either due to work or when traveling (I've biked across US2x's and Canada once). And every city and region has its own specific "car culture". It always takes me some time to adjust.
Right now I am living and working in San Diego for 2 months and I've had a bit of "car/bike culture shock" as I commute by bike. The roads all feel like freeways to me. Sometimes I can't believe the road I am on actually has a "bike lane" as cars whiz along beside me at 50+ mph. The intersections feel like they are 1/4 of a mile wide and making a left turn can mean crossing 3-4 lanes of high speed same direction traffic to get into the left turn lane. Last night I had my first car ride and we got on "the 5"- which is the freeway- and moved at the nice biking speed of 17-19 mph for a good 40 minutes until we got to our exit, where we promptly got on a multi lane road and travelled at 50+ between stoplights.
The bike culture here is much more an outgrowth of the "fitness culture" and though there are transportation cyclists they definitely feel second tier to the triathletes and road bikers.
The weather here is highly conducive to biking and it seems remarkable that I am seeing no more bikers than I do in NYC or Boston.
As a side note, having just installed solar panels on my home in the Northeast I cannot believe every house here does not have panels on the roof. A very modest solar array here would easily produce at least 20 kW per day virtually every day of the year. It seems just a bit more wedded to the automobile and traditional power plants than I expected.