First Flight Island Restaurant & Brewery

Nestled in the heart of Key West, First Flight Island Restaurant & Brewery occupies one of the island's most impressive historic buildings. This remarkable establishment stands at the corner of Whitehead and Caroline Streets in a structure famous for being the birthplace of Pan American World Airways in 1927. Aviation history enthusiasts will appreciate dining where Pan-Am's first tickets were sold, marking the beginning of an airline that revolutionized international travel.

The restaurant features a magnificent garden canopy dining area where soaring trees create a natural ceiling that sparkles with lights after sunset. Behind French doors lies the Southernmost Brewery in the USA, crafting original beers on-site. Visitors can enjoy a drink at the famous Crash Bar, uniquely named for the Sikorsky seaplane protruding through the ceiling, featuring an actual aluminum wing as its drinking surface.

For those seeking elevated dining experiences, the Tree-Top Deck provides stunning views of both the main garden and Whitehead Street. The menu showcases local seafood specialties including Whole Snapper and Swordfish alongside Caribbean-inspired cuisine such as Mojo Glazed Pork Tenderloin and Blackened Chicken Pasta.

Whether celebrating special occasions or simply enjoying a tropical getaway, guests will find First Flight's atmosphere perfect for any event. With daily lunch and dinner service plus a delightful happy hour, visitors can experience exceptional food, handcrafted beers, and authentic Key West charm in a setting unlike any other in the Florida Keys.