Cocktail Bars

Ram's Head Southernmost logo
Rams Head Southernmost
Rams Head was founded in Annapolis, Maryland and has been family owned and operated since 1989. With roots in Key West, Rams Head is proud to be part of the local community and is committed to providing the best in Food, Fun, and Beer.
Rams Head was founded in Annapolis, Maryland and has been family owned and operated since 1989. With roots in Key West, Rams Head is proud to be part of the local community and is committed to providing the best in Food, Fun, and Beer.
Jack Flats
A great local spot in the heart of Key West, Jack Flats is the best sports bar on the island. Enjoy a beer, spirits, and our generously portioned home-style food for lunch or dinner while watching the games on our 19 big screen TVs. So kick back, relax, and enjoy your time in paradise!
A great local spot in the heart of Key West, Jack Flats is the best sports bar on the island. Enjoy a beer, spirits, and our generously portioned home-style food for lunch or dinner while watching the
Dante's Pool Bar & Restaurant logo
Dante’s Pool Bar & Restaurant
Dante's an Aquaholics Paradise! A crystal clear swimming pool warmed by its cascading waterfall, friendly servers bringing you ice cold tropical libations and tasty treats as you sun, swim, dance and party. Try our mouth-watering delights, Stone crabs, lobster, oysters and always the freshest local fish, transformed into tacos, po’ boys and platters. Join us for sporting events on 17 TV’s, sunset dinners and the keys most dangerous Happy Hour! It's all about the people, both local and visito
Dante's an Aquaholics Paradise! A crystal clear swimming pool warmed by its cascading waterfall, friendly servers bringing you ice cold tropical libations and tasty treats as you sun, swim, dance and
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
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
Photo of Grand Cafe Key West
Grand Café
Featuring one of the finest wine lists in Key West, the Grand Cafe is reminiscent of café dining in Europe. Situated in an old Victorian home, the Grand Café offers a full wrap-around porch for those lazier days with a great view of Duval Street perfect to people watch. Guests can enjoy a full selection of wine, martinis, beer and, of course, delectable seafood and fine meats.
Featuring one of the finest wine lists in Key West, the Grand Cafe is reminiscent of café dining in Europe. Situated in an old Victorian home, the Grand Café offers a full wrap-around porch for thos
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
Conch Republic Seafood Company
Experience true dock-to-dish dining as you enjoy the incredible views of the Historic Seaport inside our fully open air restaurant! Often, you’ll see our very own fleet of boats unloading their catches of fresh fish, stone crab and Caribbean Lobster!
Experience true dock-to-dish dining as you enjoy the incredible views of the Historic Seaport inside our fully open air restaurant! Often, you’ll see our very own fleet of boats unloading their catc
Salty Oyster Dockside Bar + Grill logo
Salty Oyster
From Key West pinks by the dock to a Mango Overboard in your private cabana, Salty Oyster Dockside Bar & Grill offers fresh fare and tasty drinks in a comfortable atmosphere, just steps from the pool.
From Key West pinks by the dock to a Mango Overboard in your private cabana, Salty Oyster Dockside Bar & Grill offers fresh fare and tasty drinks in a comfortable atmosphere, just steps from the pool.
Four Marlins
Enjoy a culinary adventure with regional flair at Four Marlins. Savor ocean to table highlighting the freshest, locally sourced seafood and produce. Enjoy an extensive selection of the finest rums, specialty cocktails, ice-cold draft beer, and a thoughtfully selected wine list.
Enjoy a culinary adventure with regional flair at Four Marlins. Savor ocean to table highlighting the freshest, locally sourced seafood and produce. Enjoy an extensive selection of the finest rums, sp
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 berlins
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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Area: Historic Seaport