Bar, Grill & Brewery Bar

Seen in Conde Nast, People Magazine and on Food Network! we describe our restaurant, bar and micro-brewery as "American Flare with an Island Twist".

Kelly’s main level includes soaring trees that arch and create a living canopy in the main garden and sparkling lights at night creating a welcomming atmosphere for your meal day or 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 seaplane plunging through the ceiling, provides a unique drinking surface- an aluminum wing- and is located off the main garden. Sample some of the excellent homebrewed beers like Havana Red, Key West Golden and Southern Clipper Wheat.

Historic Building Front Building

Located at 301 N. Whitehead Street, on the corner of Whitehead and Caroline, stands one of Key West’s most impressive, well-known for being the birthplace of Pan American Airlines - Kelly's Caribbean. Pan-Am’s first tickets were sold out of this very building in 1927.
Kelly's has a large, covered open-bar area, an indor eating area, as well as an outdoor dining area under the canopy of lush vegetation. The hidden outdoor rooftop garden is perfect for intimate affairs and romantic Wedding receptions.

The second floor Tree-Top Deck (also know as the rooftop garden) is nestled in the tree-tops and provides a view of the lower Main Garden dining area and of Whitehead Street. The rooftop garden level is complete with restroom facilities and an indoor open air-pavilion area which is also open to the main garden below.

Namesake Front Sign

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. The actress herself invented many of the sauces used.
Should you stop on by Kelly's Caribbean... we do have her Top Gun Jacket in the "Crash Bar" area. More info on Kelly McGillis...