It might take a little extra work to track down these Key West hidden gem bars, but, hey, that’s all part of the fun. From bonafide dive bars to upscale craft cocktail and Champagne lounges, here are a few of our favorite watering holes off the beaten path.
The lovable dive bar at the corner of Truman Avenue and Grinnell Street comprises an inside air-conditioned bar, an outside tiki bar, and a liquor store complete with a drive-up window. Locals love the “first and last bar off of Duval Street” for the friendly bartenders, cheap drinks, TVs, and bar games like pool, darts, corn hole, and ping pong. 1000 Truman Ave.
The bubble gum-hued Bobby’s Monkey Bar is one of Key West’s most relaxed gay bars, beloved for its daily eight-hour-long Happy Hour, nightly karaoke, and neighborhood feel. The bartenders are excellent conversationalists and may even tell you a story or two! 900 Simonton St.
Tucked behind the famous A & B Lobster House, this speakeasy-style cocktail bar has been a local hideout since the late 40s. Settle into a soft club chair, listen to jazz, and sip on delicious innovative and classic cocktails. Berlin’s has an impressive top shelf liquor inventory and a fun make-your-own gin and tonic menu where you can select from 10 gins and three tonics to create your perfect bright and zesty concoction. 700 Front St.
The bar (1st floor) and craft cocktail lounge (2nd floor) is known for its killer 20% discount given to veterans, active-duty military, police, firefighters, EMTs, nurses, doctors, veterinarians, and all other modern day heroes that serve and help others. Other reasons we love this spot include the live music and local spirits like rum from Key West First Legal Rum Distillery and Papa’s Pilar Rum Distillery, whiskey from Key West Trading Company, and gin from St. Augustine Distillery. 506 Southard St.
Discreetly located at the corner of Truman Avenue and Duval Street, Tiger Bar and the Champagne Room is a fusion of two concepts. Tiger Bar serves up tasty international street food-inspired small plates while the vintage lounge of the Champagne Room features a rotating boutique wine list and artisanal hors d’oeuvres. 500 Truman Ave.
The friendly neighborhood bar is just steps from Duval Street and creates innovative cocktails that rival even the most lauded mixologists on the island. Try the Maria-Rita with habanero and hibiscus or the Traditional Hemingway Daiquiri. 508 Fleming St.
Located within 24 North Hotel in New Town, the Havana-esque craft cocktail lounge has put together an exciting drink menu complimented by unique charcuterie boards and nightly live music. Try out-of-this-world beverages like the Cigar Smoking Smuggler infused with smoke from a Rodriguez Reserva cigar, the 24 Carrot Gold with fresh carrot juice and Ancho Reyes chile liqueur, and the Key West Sunset for a medley of flavors and colors that perfectly captures the essence of our world famous sunset. 3820 N Roosevelt Blvd.
Looking to visit Key West’s hidden gem bars in plain sight? Plan your accommodations with 24 North Hotel Key West. Our New Town hotel has amenities you won't find in other hotels - modern rooms that are smartly furnished, a large pool, restaurant & bar, Starbucks, and shuttle service to and from Old Town. Plus, if you want some peace and quiet during your downtime, we're in just the right spot. Read more about special offers at 24 North Hotel.