First Flight Island Restaurant and Brewery

First Flight Island Restaurant and Brewery brings historic Key West dining, craft beer, garden seating, cocktails, seafood, and Caribbean-American flavor to 301 Whitehead Street in Old Town Key West. Set inside the landmark building known as the birthplace of Pan American World Airways, this restaurant gives visitors a rare chance to enjoy lunch, dinner, drinks, and happy hour in one of the island’s most aviation-rich historic settings.

The main garden dining area is one of the most memorable restaurant spaces in Key West, with soaring trees, brick pathways, tropical greenery, and evening lights creating a relaxed island atmosphere just steps from Duval Street, Mallory Square, Truman Annex, and the Historic Seaport. Inside and around the garden, guests can find Pan Am memorabilia, the Southernmost Brewery in the USA, and the well-known Crash Bar, where an airplane-wing-style bar and suspended seaplane theme add to the experience.

The menu focuses on approachable island dining with fresh seafood, burgers, flatbreads, tacos, wraps, salads, house-brewed beer, and shareable plates. First Flight is also a strong choice for visitors looking for local craft beer in Key West, with original beers brewed on property and served alongside tropical cocktails, wine, and classic bar favorites.

Daily happy hour runs from 4:00 pm to 6:00 pm at the Crash Bar, with house beer, wine, cocktail, and food specials. With lunch, dinner, brewery service, private event space, and a distinctive aviation-history setting, First Flight Island Restaurant and Brewery is a standout stop for visitors who want more than a standard meal in Key West.