Roosters. Speakeasies. Exotic orchids. Legends. It’s time to update your bar crawl with some of Key West’s Finest mixologists, funky spaces, and all around entertaining purveyors as you raise your glasses — and copper mugs — in paradise.


The Roost

Half a block off Duval on character-rich Fleming Street, The Roost is a neighborhood bar and liqueur store that has become a favorite among locals and a curious find for tourists with well “trained” eyes. The rich and earthy interior styling and spacey marbled effect floor channel a timeless feel that could place patrons in the 20th or 21st century. Try the hilariously named “Blowin’ Smoke Up Your Glass” — a titularly smoky infusion of sweet syrups, Papa’s Pilar 24YR Dark Rum, bitters, fresh lime, and pineapple. The various small plates mercifully ensure that you will have ample supplies of smoked salmon and deviled “rooster” eggs to stave off the effects of drinking on an empty stomach. 508 Fleming Street


The most unique experience for craft cocktails and gourmet small bites is at local favorite and hidden gem!
Try the Banana Daiquiri made with White, banana purée, banana liqueur, lime, brûlée, & vanilla! 423 Caroline Street


General Horseplay


The Orchid Bar

Orchid Key Inn doesn’t do crowds. In fact, you’d be hard pressed to fit more than a dozen people at this streamlined, glass enclosed, and upscale spot. Emphasizing the use of fresh herbs, fruits, infused liquors and well kept elixirs you can’t go wrong with a refreshing combination of watermelon infused vodka, fresh jalapeño, and soda by one of the team’s mixologists. Did we mention the gorgeous poolside view?1004 Duval Street

The Chart Room Bar

Located at the waterfront Pier House Resort & Spa, this previously well kept local secret is credited with providing many of Jimmy Buffet’s first gigs, supplying drinks to Mel Fisher during the search for the Atocha, and even hosting Bob Marley on innumerable occasions. The Chart Room Bar is a piece of Key West lore as it is often accredited with rich stories and zany adventures by the famous, infamous, and sometimes secretive patrons. So much so that regulars who have parted from this world have had their ashes embedded into the Chart Room’s mahogany bar top. By all means come for the wide assortment of drinks but stay for the history and signature self-served hot dogs and popcorn. 1 Duval Street