First Flight Island Restaurant and Brewery

First Flight Island Restaurant & Brewery – Key West Historic Restaurant & Southernmost Craft Brewery

First Flight Island Restaurant & Brewery delivers an immersive experience where culinary craft, aviation history, and tropical ambiance meet in the birthplace of Pan American World Airways. Located at 301 Whitehead Street in historic Old Town Key West, this landmark occupies the original 1927 ticket office where Pan Am first launched passenger air travel. Dining unfolds beneath a lush garden canopy illuminated by subtle evening lights, transforming the space into a captivating oasis for lunch, dinner, and daily happy hour specials.

A centerpiece of the venue, the dramatic Crash Bar, showcases a suspended Sikorsky-style seaplane soaring through the ceiling while cocktails are served across a gleaming bartop built from an authentic airplane wing. An upper-level Tree-Top Deck offers private event space with elevated views of tropical foliage and historic architecture, making it ideal for intimate celebrations and group gatherings.

Recognized as the Southernmost Brewery in the USA, First Flight produces small-batch beers brewed just steps from the dining garden. Signature creations such as the Sunset Clipper Citrus Wheat, influenced by Florida grapefruit and coriander, and the Old Havana Red Amber Ale, rich with cocoa-like earthiness, reflect Key West’s adventurous maritime spirit.

The kitchen presents a Caribbean-American fusion menu focused on fresh seafood and bold island flavors. Crowd-favorites include fish dip paired with crispy plantain chips, spicy jerk wings glazed in tropical heat, and the distinctive DI PARMA charcuterie-style flatbread. Main entrées showcase mahi tacos topped with mango salsa and microgreens, baby lamb chops finished with a port wine reduction, and rotating fresh catches prepared with citrus-herb blends inspired by Key West waters.

The cocktail program mirrors early Pan Am travel culture with tropical classics like the Pusser’s Painkiller featuring British navy rum, a creamy Key Lime signature cocktail, and aviation-inspired drinks such as the Pilot’s Paloma and refreshing Havana Mojito. With daily service for lunch and dinner, plus a lively happy hour featuring house beers and handcrafted cocktails, First Flight Island Restaurant & Brewery remains a must-visit destination for anyone seeking flavor, history, and authentic Key West culture in one unforgettable setting.