Let’s face it you’re one vacation and you want to get as much bang for the buck as possible and partying in Key West at an efficient dollar amount means taking advantage of Happy Hour. In this destination review two places stood out for their incredible happy hour values and one was Kellys, a pretty little perch that was started by actress Kelly McGillis.

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We ran into another couple from NJ at the bar and they raved about the wings and so we gave them a try, they come in a variety of sauces and they were nice enough to let us try them all and my goodness they were wonderful and possibly top three of all time in our travels.

The staff was friendly and very accommodating, they poured a great drink and have fresh margaritas for those of you who like to go that route, they are only $3.50 during HH and that is hard to beat.

Happy Hour runs from 4-7 but it’s best to get there on the early end as the place does fill up, even during the weekdays.

We can highly recommend Kelly’s to you. Take a gander at their menu and background story.




Located at 301 Whitehead St., on the corner of Whitehead and Caroline, stands one of Key West’s most impressive and historic buildings – Kelly’s Caribbean. Well known for being the birthplace of Pan American World Airways, Pan-Am’s first tickets were sold out of this very building in 1927. Pan Am was the principal and largest international air carriers in the United States from 1927 until its collapse on December 4, 1991. Founded in 1927 as a scheduled air mail and passenger service operating between Key West, Florida and Havana, Cuba, the airline became a major company credited with many innovations that shaped the international airline industry, including the widespread use of jet aircraft, jumbo jets and computerized reservation systems.

Our Namesake – Kelly McGillis
Kelly’s was opened in 1992 by Fred Tillman and Actress, Kelly McGillis. We are proud to carry Kelly McGillis’ name!  Noted for her various movie roles – Top Gun, Witness, The Accused – Kelly now resides in North Carolina but she does keep a watchful eye on the Kelly’s Caribbean. Should you stop on by Kelly’s Caribbean…we do have her Top Gun Jacket in the “Crash Bar” area.


Kelly’s Caribbean’s main level includes soaring trees that arch and create a living canopy in the main garden by day and sparkle with lights at night. Off the main red-bricked garden and behind French doors lies the Southernmost Brewery in the USA. The famous Crash Bar, so named for the Sikorsky sea plane plunging through the ceiling, provides a unique drinking surface – an aluminum wing – and is located off the main garden.  The second floor Tree-Top Deck is nestled in the tree-tops, it provides a view of the lower Main Garden dining area and of Whitehead Street. Both areas are great for celebrations of all kinds – your wedding party or travel group are welcome!