sixxpack saidah, i suppose i didn't give much guidance did i? i'm more foodie than gourmand, independent bookstore than books-a-million, billy reid than hugo boss, and vocal trance than tribal. having just done new orleans for halloween, i'm all "big easied" out. i was looking more for something colder, older, and outside my southeastern stomping grounds. i'll definitely be on the dance floor all night but will be ferreting out the quirky coffee houses and bookstores during the day. thanks again.
OK, well that would be a fair description of a week in NYC. The only problem with the Times Square ball-dropping scene is that the police now use crowd control, whereas it once was all open. And depending on the threat level you'll have to pass security checks that will likely prohibit large items like backpacks, or bottles.
For that reason you may have to arrive a few hours early to gain "entrance" before crowd capacity is reached and it's completely blocked, and then just wait around. Dress warmer than you normally would for whatever temperature it is that night, with hat & gloves, because hours of standing idle on sometimes windy New York streets will chill you more than you may have experienced before.
And check local online sites & newspapers for this year's Times Square rules & guidance. I believe this NYPD site will be carrying official police policy as the day approaches, as will the NYC municipal site:http://www.nyc.gov/html/nypd/html/home/home.shtml
Afterwards there aren't too many gay clubs near Times Square, they're rather spread out, NYC really not having a gay "strip" like some cities do. But straight clubs can be fun, too. Wherever you go there may be lines outside to get in, though that should diminish after midnight.
If you do decide on NYC let us know, plenty of RJ guys who know the city well, and who may also want to meet you. I live in South Florida but used to be a regular in Manhattan. And of course let me know if you instead choose South Florida. Fort Lauderdale/Wilton Manors has most of the gay clubs, while South Beach should be having some outdoor partying, like along Ocean Drive and on Lincoln Mall. But neither really has some of the other things you say you're looking for, not like compared to NYC, and certainly not as cold.