the two cities I ride in most are Boston and NYC.
Boston has limited bike infrastructure, very aggressive drivers, potholed narrow streets, constant construction, tons of on street parking and double parking. It's few MUP's are poorly maintained but part of a gorgeous urban park system designed by Frederick Law Olmstead that make the scenery worth the ride in many cases. But I ride the streets and the Boston- Watertown MUP daily and love it.
NYC used to be a nightmare of mean streets and high speed avenues and in some ways it still is. But the improvements in infrastructure, in particular the west side greenway and the adding of bike lanes has moved it into the lead of the 2 towns for me. I still can't believe what a difference a few ribbons of asphalt and some stripes on the street made in that town. That and the fact that it just hit it's peak capacity of private autos and trucks and it's citizens are getting sick of all the cars. So the catering to autocentricity that still exists in Boston is diminishing in Manhattan. The city has also cut back on the number of hours that automobiles can drive in Central Park and it can be a real oasis- just watch for all the peds, bikes, carriages and joggers.