Pepe’s Cafe & Steakhouse

Pepe’s Cafe has operated continuously since 1909, a run of more than a century that makes it the oldest eatery in the Florida Keys and the second oldest restaurant in the entire state, a distinction that alone would justify a visit even before considering what actually comes out of the kitchen on any given day.

The restaurant treats its old fashioned approach as a point of pride rather than a limitation, noting that the only freezer in the house is reserved for ice cream, a small but telling detail about a kitchen still committed to daily fresh made bread, fresh squeezed juices, and oysters shucked to order rather than the shortcuts a century old restaurant could easily have adopted along the way.

The bar has picked up real recognition in its own right, winning best mojito and best margarita at the 2026 BUBBAS Awards, a reminder that a restaurant this old has not simply been coasting on nostalgia but continues to compete seriously against newer restaurants for the same local accolades.

The dining room and walls carry more than a century of accumulated history, including photographs of famous patrons, President Harry Truman among them, tying the restaurant directly to Key West’s mid century role as a winter retreat for the highest levels of American political life during Truman’s presidency.

Hours run long, from seven thirty in the morning until nine thirty at night daily, with a happy hour from four to six that has become a specific draw of its own for the oyster specials on offer, giving the restaurant a role in the neighborhood that spans from breakfast through a full dinner service.

The restaurant is also pet friendly, fitting for a Key West institution in a town where dogs are a common sight at outdoor tables throughout the historic district, and one visitor’s description of the place as a totally underrated spot with so much history packed into such a small space captures the restaurant’s appeal well.

For a genuine taste of Key West history alongside a properly made cocktail and fresh oysters, Pepe’s Cafe offers more than a century of continuous operation behind every meal, a rare kind of authenticity in a town where restaurants often turn over every few tourist seasons, and a reminder of just how long this small island has been welcoming visitors to its tables, decades before Duval Street ever became the entertainment strip most tourists now associate with the name Key West.