Caroline's Other Side

Bar · Key West

Caroline's Other Side

Bar · Key West

2

429 Caroline St, Key West, FL 33040

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Caroline's Other Side by Photo courtesy of the Other Side
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Caroline's Other Side by null
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Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null
Caroline's Other Side by null

Highlights

Nestled in the historic Porter Mansion just off Duval Street, The Other Side serves up exquisite craft cocktails in a chic, tropical hideaway.  

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429 Caroline St, Key West, FL 33040 Get directions

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429 Caroline St, Key West, FL 33040 Get directions

+1 305 294 7511
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Jul 4, 2025

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@afar

"The Other Side: New-School Cocktails in Old-School Key West In the land of piña coladas and light beers, The Other Side cocktail lounge is chiseling out new booze territory one ice globe at a time. Drinks, loosely inspired by the Keys, are like nothing else on the island. There’s the frothy Ramon Fizz, a mix of gin, lime, cream, egg whites, and fleur d’orange, or twists like the fennel martini, and for purists, a serious list of bourbon, whiskeys, and 16 rums. The small space feels a world away from the beach, with touches of old-school Hollywood glamour: a marble-topped bar, padded white leather bar stools, and a painting of a peacock tail fanned across one wall. When you need a break from the sun and throngs, this is the place to tuck in with a good book, or a good date (snag the chess board if you’re feeling ambitious)."

The Best Bars in Key West
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@cntraveler

"Any bar that isn't a tourist trap is a good thing in Key West, never mind one in a historic mansion just a few steps off Duval Street's main drag—and this sophisticated speakeasy with just a hint of kitsch delivers, with its immense list of spirits, along with a few are nice wines and local craft beers. But it's the cocktails that keep people coming back. The bar does a great job with the classics, but the more creative concoctions are where things really shine; on a recent visit, the Summer Thyme, made with vodka, raspberry puree, apricot liqueur, lime juice, peach bitters, and thyme syrup impressed. But if nothing seems to suit you, talk to the bartenders; even when the bar is buzzing, they'll turn all their attention toward you, and make you feel like you’re their only customer." - Jennifer M. Wood

10 Best Bars in Key West | Condé Nast Traveler
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Steven Smith

Google
Quite possibly some of the BEST drinks and atmosphere I have experienced in Key West! Quiet, quaint, classy, and amazing cocktails! We have been coming to Key West yearly for more than 20 years and this is our first time here and wish we had found it sooner! If you need a break from the loud, crowded, hustle and bustle, of the everyday Key West bars...but still want the alcohol...the DEFINITELY come here! The tastes and smells are amazing, you will not regret it!

Adam D'Amore

Google
The best cocktails of the trip... Maybe the most amazing cocktails that I have ever had. So good. It's probably for the best that I don't live nearby... Neither my wallet nor my liver could survive. Mixologist was awesome. It's off menu, but her The Last Word was indeed the last word on the subject: exquisite. If the music were a bit quieter, this place would get six stars for sure.

Blair Johnson

Google
Awesome music, and an amazing dark and stormy! This isn't your local dive, this is a place you come if you are actually cool and want a proper cocktail. Frank Sinatra is playing in the background as the mixologist burns my lime with a blow torch. I would come here every night if I could.

Mariah Murphy

Google
Wish I could give 4.5 stars. The cocktails were perfection. The decor was not to my taste, but it gets an A for effort. The Zoltar fortune telling machine in the back was SO loud and very obnoxious.

Chris Mann

Google
craft cocktails, great setting and staff. sick selection of spirits.

Matthew Poe

Google
Hands down the best bar we went to in Key West; I'd go further and say that it compares favorably to most of the best places doing classic cocktails in NYC these days. Fantastic drinks, cool crowd, hip space, great artwork, charming and friendly bar staff. If you like classic cocktails, go, go, go!

Matthew Kahn

Google
After two visits and a thorough sampling of their libations, I can't say enough good things about this place. The decor is cool but not pretentious, the music is a mix of old school and top 40 and the cocktails are strong, consistent and carefully made. When you've had your fill of sour mix at the many low-end bars in Duval Street, stop in here for a REAL drink.

Toby Weir-Jones

Google
Without a doubt, the best cocktails in Key West. Tim, Cassie, and Lisa serve up premium cocktails with innovative recipes largely informed by Tim's experience and background. He's spent time honing the trade in St. Louis at Sancturia, and a number of other stops before ending up down south. This is not a place for cheap shots and rowdiness, but you'll run into a diverse crowd of tourists, Navy airmen, and outspoken locals as you sit at the bar and peruse the options. Well worth a visit if you value a deft touch in your spirits and the benefit of experience and wisdom in their creation.