History, handcrafted beer, and exceptional island dining come together at First Flight Island Restaurant & Brewery, one of Key West's most distinctive restaurants. Located in the historic building where Pan American World Airways (Pan Am) sold its very first airline tickets in 1927, this unique destination blends aviation history with fresh Florida cuisine and award-worthy craft beer.
Whether you're enjoying lunch beneath a canopy of tropical trees, sipping a house-brewed beer at the famous Crash Bar, or dining on the elevated Tree Top Deck, First Flight offers an experience unlike anywhere else in Key West.
The Birthplace of Pan Am
Long before it became one of Key West's most popular restaurants, this historic building played an important role in aviation history. In 1927, Pan American World Airways began selling tickets here for scheduled air mail and passenger service between Key West and Havana, Cuba. The airline would later become one of the world's most influential international carriers, helping pioneer innovations such as jet travel, jumbo jets, and computerized reservation systems.
Today, the building celebrates that legacy with aviation-inspired décor, historic photographs, and unique design elements throughout the property.
Beautiful Gardens and the Famous Crash Bar
First Flight offers several unique dining experiences, each with its own atmosphere.
The Main Garden features towering tropical trees that create a natural canopy over outdoor dining areas, making it one of the most beautiful courtyards in Key West.
Photo Credit: First Flight
Inside, the legendary Crash Bar is impossible to miss. A vintage Sikorsky seaplane appears to have crashed through the ceiling, while the bar itself is constructed from an aircraft wing. Just beyond the bar is the Southernmost Brewery in the continental United States, where First Flight brews several of its own craft beers on-site.
For private gatherings and special occasions, the Tree Top Deck overlooks the gardens below and offers an elevated setting for celebrations, rehearsal dinners, weddings, and group events.
Fresh Florida Cuisine and House-Brewed Beer
First Flight's menu combines fresh local seafood with American favorites and island-inspired specialties.
Photo Credit: First Flight
Popular menu selections include:
- Fresh local seafood
- Mahi-Mahi Sandwich
- Fish & Chips
- Whole Yellowtail Snapper
- Seafood Fettuccine
- Fish Tacos
- Brewery Burger
- Jerk Chicken Sandwich
- House-smoked brisket dishes
- Original craft beers brewed on-site
The restaurant also serves handcrafted cocktails, wines, and a large selection of Florida craft beers alongside its own signature brews.
Just Minutes from Key West Express
First Flight is located approximately 0.6 miles from the Key West Express terminal, about a 12-minute walk through the Historic Seaport into Old Town.
Nearby attractions include:
- Duval Street
- Ernest Hemingway Home & Museum
- Mel Fisher Maritime Museum
- Key West Lighthouse
- Mallory Square
- Sloppy Joe's Bar
- Captain Tony's Saloon
- Key West Historic Seaport
Its central location makes it an excellent stop for lunch, dinner, happy hour, or a relaxing craft beer while exploring Key West.
Frequently Asked Questions
Where is First Flight Island Restaurant & Brewery located?
First Flight is located at 301 Whitehead Street at the corner of Whitehead and Caroline Streets in Old Town Key West.
Why is it called First Flight?
The restaurant occupies the historic building where Pan American World Airways sold its first airline tickets in 1927, inspiring the restaurant's aviation-themed name.
Does First Flight brew its own beer?
Yes. The restaurant is home to the Southernmost Brewery, where several original craft beers are brewed on-site.
What is the Crash Bar?
The Crash Bar is First Flight's signature bar featuring a vintage Sikorsky seaplane appearing to crash through the ceiling, with a unique aircraft-wing bar beneath it.
How far is First Flight from the Key West Express terminal?
The restaurant is approximately 0.6 miles away, or about a 12-minute walk from the ferry terminal.
Does First Flight have outdoor seating?
Yes. Guests can dine beneath a beautiful tropical garden canopy or enjoy elevated seating on the Tree Top Deck overlooking Whitehead Street.
Is First Flight family-friendly?
Absolutely. The combination of fascinating aviation history, spacious outdoor seating, fresh Florida cuisine, and a relaxed atmosphere makes it a popular choice for families visiting Key West.
Discover One of Key West's Most Historic Restaurants
From its remarkable aviation history to its craft brewery, tropical gardens, and fresh island cuisine, First Flight Island Restaurant & Brewery offers an unforgettable dining experience. Travel aboard Key West Express, enjoy a short walk into Old Town, and discover one of the most unique restaurants in Key West.
