About First Flight Island Restaurant & Brewery
On October 28th, 1927, the first ticket for an American international commercial flight was purchased at 301 Whitehead Street in Key West — a Pan American Airways service to Havana, Cuba, a journey of ninety miles across the Straits of Florida. The building that housed Pan American's first office is still there, and First Flight Island Restaurant & Brewery now occupies it with a respect for the history and a menu that uses the address's significance as a starting point rather than a marketing device.
The physical space is extraordinary. The interior retains Pan American memorabilia — photographs, artifacts, documents — displayed with the seriousness of a museum rather than the kitsch of a theme restaurant. A bar made from an actual airplane wing serves as the indoor-outdoor crash bar that connects the indoor dining room to the garden. And then there is the garden itself: a canopied outdoor dining space beneath the interlocked canopies of two massive strangler fig trees, which create an enclosed natural architecture of filtered light and moving shadow that no designed dining room could replicate. It is one of the most beautiful outdoor dining environments in the Florida Keys.
The brewery, which operates on the premises as the southernmost craft brewery in the United States, produces three flagship beers and rotating seasonal offerings. Executive Chef Ben Schneller has designed the menu to pair with the house beers while standing independently as a serious restaurant menu. Whole snapper, sourced from the Florida Keys' productive fishing grounds, is roasted with the confidence of a kitchen that knows its seafood. The swordfish is treated with the restraint that excellent fish deserves. The Mojo Glazed Pork Tenderloin connects to the island's Cuban culinary heritage. The Blackened Chicken Pasta is one of the menu's more accessible options and consistently earns strong reviews from the broadest range of diners.
The happy hour from 4pm to 6pm makes First Flight one of Key West's better value propositions during the early evening window. The combination of discounted craft beer and bar bites in the garden — with the light falling through the strangler figs as the afternoon heat softens — is one of those Key West experiences that visitors describe for years afterward.
Lunch is served daily and represents excellent value, with the full menu available alongside the brewery's flagship beers at prices that make a midday meal here a sensible decision for visitors with an afternoon to fill intelligently. The seasonal changes to the menu keep regulars returning and ensure that what Chef Schneller is serving reflects the current state of the Florida Keys larder.
Best Occasion: Birthday
The garden dining room under the strangler figs creates a natural sense of occasion that requires no additional decoration. A birthday group of four to ten people sits comfortably in the outdoor space, with craft beer flowing in a format that accommodates different preferences across a group. The history of the building gives the dinner a conversation anchor — where you are and what happened here in 1927 — that most birthday dinners lack. And the Key West setting means no one arrives in a bad mood.