The Happiest Hour

Picture Don Draper on vacation: rum cocktail in hand, wind blowing through that meticulous coif. While you may never have Jon Hamm’s cut-from-glass jawline (sorry), you can make like a Sterling Cooper adman at leisure in this retro-kitted tiki lounge, from Tijuana Picnic partners Jon Neidich and Jim Kearns. The bi-level bar is crammed with mid-20th-century curios—a ’60s pop soundtrack; mod, half-moon booths; waitresses in Chuck Taylors—but it’s the customizable cocktails and breezy vibe that win over the crowd.

ORDER THIS: Renowned barman Kearns (Pegu Club, the NoMad) prompts you to pick your poison, creating a cocktail list ($12) that seamlessly matches a variety of spirits. The Link Ray—playing on Cel-Ray soda with house-made celery pop, zippy lime and Suze bitters—is the most versatile of the bunch, available with a choice of rum, gin or tequila. Sweet rum helps play up the drink’s natural sugars, gin mirrors the celery’s vegetal brightness, and the jalape–o-infused tequila proves a fiery foil to the mild quaff. Skip the Little Red Dress, a bitter cocoa-and-strawberry flop, in favor of a Sugar Shack: With maple-syrup sweetness and a slug of toffee-tinged Evan Williams bourbon, it’ll tickle you and your inner child.

GOOD FOR: Cheeky ’50s-housewife–inspired snacks. The dinerlike placemat-menu ranges from light bites like hot-sauced cucumbers ($6) and sautéed brussels sprouts ($6) to the hulking Happiest Burger ($12), smothered in American cheese and confit onions. Before getting tucked into a fluffy Martin’s potato roll, the pair of flattop-griddled patties is slathered in a relish-forward secret sauce that oozes from every edge and requires some serious finger-lickin’—but you’ll happily oblige.

THE CLINCHER: You’d be hard-pressed to find a group that didn’t fit in at the floating horseshoe bar or low-lit dining room. The crowd of twentysomethings spans off-hours suits sipping Scotch on the rocks, bubbly girl groups clinking wine glasses, polo-clad bros glugging Miller High Life and couples cozying over cocktails in velvet booths. Take your buddies, bring your bae, or go stag—here, a top-rate happy hour is anyone’s game.