The crusty fishing spot at Long Island's tip is more Key (than Kanye) West: It has kitschy, shack-style share houses with names like Captain Dusty's, and the locals are so wary of visitors they'll squint at you when you're on line at the grocery store—just like they do on the Florida island. You can tally the Duval Street tees on staff in the dive bars and diners around town for proof (I spotted three in one day), but undoubtedly the clincher is that Conch Republic national bard Jimmy Buffett has spent a chunk of his millions on a sprawl nearby.

And just like Key West, Montauk saltily resists all attempts to unify it with the surrounding towns. Every summer, the bar czars—for whom the Hamptons spew profits—attempt to open a new scene-y spot there to replicate successes further west. It never works for more than a season. That was true for Backyard at Sole East; a year in, it soldiers on with a new chef, but is now gloomily people-free. The waterfront Sunset Saloon should have been a slam-dunk spot for sundowners, if only the sand were cleaner and the furniture a grade up from garden.

The '08 contender—as New Yorkers have been heftily reminded in recent weeks—is the white-walled, St. Bart's-esque Surf Lodge (pictured). The remade Lakeside Inn is now a month into its new incarnation, and it's a terrific place—stiff Dark & Stormies, lounge-y waterfront patio, quick-to-help check-in clerks. But the problem is the first-season crowd. The floppy hatted girls, stringy-haired dudes, and skimpily outfitted Brazilians co-opted as servers all look as if they'd be hard-pressed to find Montauk on a map.

That's the big issue with the Surf Lodge and company: Rather than proud Montaukers, part-time or otherwise, they've been overrun by cliques of wannabe Southamptonites, biding time until they can afford swishier shares further west. Me? I'd rather hole up there with the crackpots and conspiracy theorists who helped the government chit-chat with aliens. Oh, and Jimmy Buffett.