Cocktail Bars

photo of sloppy joes
Sloppy Joes
As one of Key West’s most iconic locations and the favorite watering hole of Ernest Hemingway, Sloppy Joe’s boasts visitors from all over the world who come to enjoy their favorite beverage, true Key West atmosphere, and high quality cuisine. There’s always a party in the main bar and Joe’s Tap Room sports a large variety of crafted and specialty beers. Live musical entertainment begins at 12 in the afternoon and rocks until 2:00 a.m.!
As one of Key West’s most iconic locations and the favorite watering hole of Ernest Hemingway, Sloppy Joe’s boasts visitors from all over the world who come to enjoy their favorite beverage, true Key West atmosphere, and high quality cuisine. There’s always a party in the main bar and Joe’s Tap Room sports a large variety of crafted and specialty beers. Live musical entertainment begins at 12 in the afternoon and rocks until 2:00 a.m.!
Blue Macaw
The Blue Macaw brings a little piece of the Caribbean to Key West. Located at the entrance of Bahama Village on the corner of Whitehead and Petronia Streets, Blue Macaw features a delicious menu of local seafood, salads and burgers. Blue Macaw also features the only build your own Bloody Mary bar on the island with over 50 different ingredients to choose from. Live music and a tropical atmosphere make the Blue Macaw a favorite with locals and visitors alike!
The Blue Macaw brings a little piece of the Caribbean to Key West. Located at the entrance of Bahama Village on the corner of Whitehead and Petronia Streets, Blue Macaw features a delicious menu of local seafood, salads and burgers. Blue Macaw also features the only build your own Bloody Mary bar on the island with over 50 different ingredients to choose from. Live music and a tropical atmosphere make the Blue Macaw a favorite with locals and visitors alike!
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Berlin’s Martini and Cigar Bar
A perfect conclusion to any evening would be a visit to Berln’s Martini and Cigar Bar. Relax in their oversize classic furnishings while peering out into the Key West Harbor. Their signature martinis and dessert wine complement an array of cigars. Choose from their selection of rare smokes or bring your own to sample. There is no other place on the island like this.
A perfect conclusion to any evening would be a visit to Berln’s Martini and Cigar Bar. Relax in their oversize classic furnishings while peering out into the Key West Harbor. Their signature martini
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Little Room Jazz Club
The Little Room Jazz Club is situated on the quieter side of Duval Street. Featuring live music nightly from some of the world’s best blue and jazz musicians around. This cozy club opens at 4pm daily, they serve a large selection of craft beer and wine.
The Little Room Jazz Club is situated on the quieter side of Duval Street. Featuring live music nightly from some of the world’s best blue and jazz musicians around. This cozy club opens at 4pm dail
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Don’s Place
Don’s Place, a “a ‘locals’ bar for tourists. Located at the corner of Truman and Grinnel, Streets, it is an inside air-conditioned bar with an outside tiki bar. Play a game of pool or darts inside or challenge someone in a game of corn hole, ping pong or foosball at the outside tiki-bar while watching your favorite game on the tube. Need to take some liquor home? Its drive up window makes it very convenient. Don’s is the first and last bar you hit off of Duval Street.
Don’s Place, a “a ‘locals’ bar for tourists. Located at the corner of Truman and Grinnel, Streets, it is an inside air-conditioned bar with an outside tiki bar. Play a game of pool or darts in
photo of the rum bar
The Rum Bar
Situated in the home of the late Raul Vaquez, a cigar selector and rum-runner of the early 1920’s, the Rum Bar has the largest selection of rums on the island. Spectacular cocktails, not just rum, await you as you sit quietly on the porch watching the passerby’s on Duval Street. Located on the first floor of the Speakeasy Inn, this laid back spot is a must see on your visit.
Situated in the home of the late Raul Vaquez, a cigar selector and rum-runner of the early 1920’s, the Rum Bar has the largest selection of rums on the island. Spectacular cocktails, not just rum, a
photo of louies upper deck
Louie’s Upper Deck
Magical panoramic views of the Atlantic Ocean await you at the Upper Deck at Louie’s. Fine wines by the glass or bottle are served as a perfect compliment to the small plates of focaccia, carpaccio, oven-fresh gourmet pizzas and more. Open 5-10pm, Tuesday through Saturday. A local and visitor favorite for over 25 years.
Magical panoramic views of the Atlantic Ocean await you at the Upper Deck at Louie’s. Fine wines by the glass or bottle are served as a perfect compliment to the small plates of focaccia, carpaccio,
photo of sunset pier
Sunset Pier
Adjacent to Mallory Square along the boardwalk you will find the Sunset Pier. Enjoy breathtaking views of the world famous sunset while indulging in Caribbean delights from their tiki-bar. Nightly music and dancing surround you as you perch atop one of their waterfront bar stools. Sip on a tropical beverage as your watch the sunset into the horizon making it the perfect ending to a marvelous day.
Adjacent to Mallory Square along the boardwalk you will find the Sunset Pier. Enjoy breathtaking views of the world famous sunset while indulging in Caribbean delights from their tiki-bar. Nightly mus
theotherside
The Other Side
Welcome to The Other Side. Upon entering door number 1, you will be transported back in time when the cocktail was more than just a drink, but a handcrafted libation prepared with precision and passion just for you. They prepare all of their cocktails with the freshest ingredients and finest spirits. You can find The Other Side hidden away in the old Porter mansion across the hall from The Porch. Don't forget to get your fortune with Zoltar! Yes, the real Zoltar! Doors open at 5pm daily.
Welcome to The Other Side. Upon entering door number 1, you will be transported back in time when the cocktail was more than just a drink, but a handcrafted libation prepared with precision and passio