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Kelly’s Caribbean Bar

Kelly’s Caribbean Bar in Key West has perfected the art of lazy afternoon drinking and will be a feature stop on the Conched in Key West Bar Crawl.  Here’s more.


Kelly’s Caribbean Bar – Key West

As far as island restaurants go, Kelly’s Caribbean in Key West, FL has just about all the bases covered.  They’ve got great food, wonderful drinks, good service, a beautiful atmosphere and to top it off, some of the best Happy Hour Specials in all of the Florida Keys.

This little oasis at the corner of Caroline and Whitehead Street was opened in 1991 by actor Kelly McGillis, of Top Gun fame.  Years ago, the historic buildings that house Kelly’s were moved from the end of Duval Street where they were once the headquarters of Pan American Airlines.  Rumor has it that the very first Pan Am tickets were sold out of the offices in these buildings.  The sign out from reads: Birthplace of Pan American World Airways – This building was the first office. 

Following an amazing restoration in the early ’90’s, the perfect atmosphere for a laid back restaurant and bar was created.  Two buildings encircle a large Banyan Tree shaded dining patio.  A triangular bar (half indoors, half outside) is perched up on a deck with plenty of space to enjoy a few rounds of drinks with friends and their micro-brewery is neatly tucked into a space in one of the back buildings and is constantly cranking out good beer.  All of this just steps from Key West’s famous Duval Street.

Most tourists eventually find their way into Kelly’s for a bit of refreshment, but this place is a favorite for Key West locals during their legendary Happy Hour.  It draws a huge, rowdy crowd and for good reason.  From 4-7pm every day, goblets of the house-made beer are only $2, well-drinks are $2.50, Margaritas and Mount Gay Rum Punches are $3 and a pound of hot wings are $4.  This is one of the best deals on the island and that’s saying something for a place that lives by the happy hour.


So, next time you find yourself hungry and thirsty in Key West, make your way to Kelly’s Caribbean Bar for a drinking and dining experience you won’t soon forget.

….and if you’re in Key West on September 22nd, be sure to join us for the Conched in Key West Charity Bar Crawl.  We will be stopping in at Kelly’s for a taste of the famous Mount Gay Rum Punch.  Cheers


Kelly’s Caribbean Bar, Grill & Restaurant
301 Whitehead St, Key West, FL 33040
(305) 293-7897