New York

While continuing to sport swim trunks bespeaks an admirable devotion to summer, no amount of testi-retracting stubborness can delay winter's icy grip. Instead, hit up Puerto Rico's Encanto Beach Club, kicking off November 2nd.

EBC's a massive, palm tree'd expansion of the El San Juan Hotel & Casino, designed by the guy behind Buddha Bar (which is still open). Poolside living's taken to another, unbreakable-glass'd level, starting with three tiki hut cabanas equipped with wifi, flat screens, minibar, safe, etc; rent one, and the staff'll kick off your mornings by wheeling you bedside cartfuls of mojitos, known locally as los hair del pero. Whether shacking up there, or lounging on one of the additional 24 day beds, you'll enjoy Caribbean grill grub (e.g., shark panini, mango sushi, lobster crepes), plus poolside drink service and gambling lessons from the casino staff, the latter being gratis -- because when you're learning how to lose money, it's important to be frugal.

Other Encanto odds and ends include a rotating roster of international DJs, pre-programmed iPods, and poolside Spanish lessons -- after which you'll be able to confide to a cabana boy, "My balls have come alive, where is the bathroom?"