Berlin’s Cigar & Cocktail

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.”

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.