Novice smokers are welcome at Philadelphia's quintessential cigar bar, but Mahogany caters more to seasoned puffers with its menu of top-notch tobaccos and private humidor lockers (annual rental fee: $600). Mostly older gents hang here, sipping and smoking while seated in high-backed paisley-print armchairs. You're allowed to bring your own cigars, too; Stop at Holt's Cigar Company, located on the floor below Mahogany.

The Philadelphia infiltration of chain restaurants yielded this lesser-known English pub and restaurant franchise a few years back, a theme that you might not pick up on from the more-or-less Americanized menu. That's no matter for cigar smokers—take a seat in the Burgundy Room, choose from F&H's selection of 13 stogies and puff till closing.

Drank one too many cups of Earl Grey at the Ritz's afternoon tea? Wind down with an after-dark indulgence at the Ritz-Carlton's Vault, tucked deep away from street noise and hotel traffic. Home to sink-in couches, super-sized martinis and a stellar choice of cigars, both men and women light up here.

Hanging out at any jazz haunt just wouldn't seem authentic without clouds of smoke swirling around the saxophonist. This swanky subterranean restaurant and lounge takes cigar-chomping one step further and lets smokers hang at the bar, day or night, and inhale in peace.

If you're looking for a piece of history in uber-trendy Northern Liberties—make that the entire city—look no further than one of the oldest bars in Philly. Cigar smoking is allowed any time of day, anywhere in the place, but it would be criminal to not light up while throwing back a classic drink at the behemoth Victorian bar.