Ultimate Guide To The History of Havana

The history of Havana is deeply connected to Key West. Before the Revolution, there was regular ferry service between the two islands, and Cuban culture flowed freely. El Mesón de Pepe's founder, Pepe Díaz, fled Cuba after the Revolution and brought his family's recipes and cultural memory to Key West. Understanding Havana's history is essential to understanding Key West's identity.

Havana Before the Revolution

For centuries, Havana and Key West were sister cities. Regular ferry and shipping traffic moved people, tobacco, food, and music between the two islands. Cuban cigar makers established factories in Key West in the 1800s, drawn by the proximity — only ninety miles of water separated the two. Havana was a cosmopolitan port city, and its influence shaped Key West's architecture, cuisine, and culture. Read more in our history of Key West and Cuba.

The Cigar Connection

Havana's cigar industry was the economic engine that linked the two cities. Key West became one of the wealthiest cities per capita in the United States thanks to Cuban cigar factories. The tradition of cigar making in Key West grew directly from Havana's expertise, and the historic William Wall Warehouse that houses El Mesón de Pepe is a physical reminder of that era.

Music and Culture

Havana exported more than tobacco. Afro-Cuban rhythms, salsa, and son cubano traveled across the strait and became part of Key West's musical identity. Today, the nightly live salsa music at El Mesón de Pepe's patio bar is a direct continuation of that cultural exchange — the same sounds that filled Havana's streets now animate the Sunset Celebration at Mallory Square.

Pepe Díaz's Journey from Cuba to Key West

After the Revolution, many Cubans fled to Key West, carrying their recipes, music, and memories. Pepe Díaz was among them. He founded El Mesón de Pepe in 1986 as a living museum of the Cuba he remembered — the food, the music, the warmth. Read the full story of El Mesón de Pepe and learn about traditional Cuban cuisine to understand how Havana's legacy lives on at Mallory Square.