Berlin's Cigar & Cocktail Bar, Florida

Puffing away in Key West, 90 miles from Havana.

On a windy day in Key West, it's possible to catch a faint whiff of the sweet tobacco growing 90 miles away in Cuba's Vuelta Abajo—or so the legend goes. In reality, that's probably just the smoke wafting out of Berlin's Cigar & Cocktail Bar.

Easygoing yet elegant, Berlin's is a calm oasis in a raucous town. Nights on Duval Street (Key West's main strip of bars, restaurants and souvenir shops) get loud. Though the town hosts far fewer smugglers, treasure hunters and wayward sailors than it did 100 years ago, pleasure-seeking tourists and wanderlusting vagabonds seem more than willing to carry on the town's tradition of debauchery. The music at Berlin's—Frank Sinatra's "That's Life," for example—contrasts sharply with that of Duval Street's other cantinas, where a more common jukebox selection is Jimmy Buffet's "Why Don't We Get Drunk and Screw."

Not that Berlin's isn't fun. It is, but in a mellower, let's-have-a-drink-and-a-cigar kind of way. Echoing the laid-back island attitude for which the locals are famous, it's a gentlemen's club minus the pomp of conventional gentlemen's clubs. The cigar lounge has no dress code (except that everyone must be dressed, unlike several other places in town), women are more than welcome (the cigar menu includes, according to manager Michelle Leonard, "thinner, less robust, lady-friendly sizes") and membership isn't necessary (nor is bringing a fat wad of cash).

The bar is located on Front Street, just off Duval, on the second floor of a waterfront building. Inside, the view from the corner couches or plush leather chairs is vintage Key West: fishing boats and yachts moored in the marina under a starry sky, with a huge 30-year-old red-and- white sign advertising Alonzo & Berlin's Lobster House, the bar's parent establishment, lending the scene a neon cast. High-backed booths line Berlin's mahogany walls, and some 10 tables, each with at least one cigar ashtray, encourage conversation.

"What's special about the room is that it has a bar area, living area with couches and coffee tables, tables for backgammon, and a baby grand piano for weekend jazz nights," said co-manager Kathleen Peace. "All areas of relaxation and conversation are covered."

Berlin's shares the building with the Lobster House, a Key West institution in the '50s and '60s. It closed in the mid-'90s but was reopened two years ago by Paul Tripp, who also owns Berlin's, a first-floor raw bar called Alonzo's and two other Key West eateries. With two restaurants on the premises, Berlin's gets a good portion of its crowd from well-fed diners who amble upstairs or next door for a post-meal smoke and a coffee—then maybe something stronger. The bar is stocked with after-dinner liquors, single-malt Scotches, Bourbons and other top-shelf spirits. Perhaps Berlin's greatest strength is its prices—a 12-year-old McCallum is just $7.50 and a highball of Maker's Mark is only $5. The all-American wine list is extensive and fairly priced, though, oddly enough, it lacks vintage dates.

With five cigar shops within a half-mile radius of the A&B compound, Berlin's probably doesn't need to carry cigars, but what's a cigar bar without the smokes? All cigars come in several sizes (mostly Churchills, robustos and panetelas), but every size costs the same: Cohibas ($16.50), Montecristos ($14), Macanudos ($12), La Gloria Cubanas ($7.50), Dunhills ($12.50) and a local brand called Vanilla Tattoo ($5.50).

Berlin's closes at midnight, right about when things are getting crazy on Duval Street. Unless you're hitting the hay to prepare for a day of deep-sea fishing, you can drink like a fish at one of the island's countless saloons. But for a mellow night on the town on this everything-friendly island, Berlin's is a place to avoid the hedonists and catch a quiet moment.

Berlin's Cigar & Cocktail Bar
700 Front Street
Key West, Florida 33040

5:30 p.m. to midnight, seven days a week