Our Story

All About Kelly’s History in Key West:

20150311_Kellys-Rebecca-Gusto_3003  Welcome to Kelly's

Welcome to Kelly’s

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!

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6 thoughts on “Our Story

  1. A great aviation pub with good cold local beer with lots of cool aviation history✈️

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