Key West and Cuba are separated by roughly 90 miles of water, but their shared story has been unfolding for generations. Cuban immigrants helped build the island's economy, supported the struggle for Cuban independence and left a lasting mark on local politics, education, art, architecture, language and food.
That heritage is not confined to a museum display. You can experience it in a strong cup of café cubano, a historic building on Duval Street, a plate of roast pork and plantains, or the Spanish name many locals still use for Key West: Cayo Hueso. Arriving aboard Key West Express places you near the Old Town streets where much of this history unfolded.
Why Key West and Cuba Share Such a Deep Connection
Key West sits closer to Havana than it does to Miami. For much of the island's history, the Florida Straits functioned less like a barrier and more like a maritime highway. Fishing boats, merchant vessels and passenger ships carried people, goods, news and ideas between the two islands.
Spain controlled Florida for long periods before the territory formally transferred to the United States in 1821. The Spanish name Cayo Hueso, commonly translated as “Bone Key,” gradually became “Key West” in English. Cuban residents began settling on the island during its early decades as an American port, and later waves of immigration made the cultural connection much stronger.
The Ten Years' War, which began in Cuba in 1868, sent people across the straits in search of political freedom, safety and economic opportunity. By the late 1800s, Key West had a large and influential Cuban community with Spanish-language newspapers, businesses, schools, social organizations and political clubs.
Cuban Immigrants Helped Transform Key West
Cigar manufacturing became the economic engine behind much of this growth. Cuban tobacco and skilled Cuban cigar rollers helped Key West develop into a major manufacturing center. Samuel Seidenberg established the island's first clear-Havana cigar factory in 1867, and the industry expanded rapidly during the following decades.
The factories supported far more than cigar rollers. Printers, carpenters, merchants, shipping companies and neighborhood businesses all benefited. Cuban workers and their families built communities around those jobs, contributing to the population and prosperity that made Key West Florida's largest and wealthiest city by 1890.
Photo Credit: Joann Ogonowski / Florida Keys Photo Adventure.
Cuban residents also became part of civic life. Carlos Manuel de Céspedes y Céspedes, a Cuban exile and independence supporter, was elected mayor of Key West in 1876. His election reflected how deeply Cuban residents had become involved in the island's public affairs.
This article focuses on the wider cultural story. For a closer look at the factories, workers and manufacturing techniques behind the boom, read Cuban Cigars and Key West: The Industry That Shaped an Island.
The San Carlos Institute: A Center of Cuban Life
Few places represent Key West's Cuban heritage as clearly as the San Carlos Institute at 516 Duval Street. Cuban exiles founded the institution in 1871 as a patriotic, educational and cultural center. It became a meeting place, theater, library and school for the island's Cuban community.
For more than a century, the San Carlos operated as one of the nation's early bilingual and racially integrated schools. Students learned in Spanish and English, making the building an important part of both Cuban-American and Key West educational history.
Photo Credit: Avbelli, own work, CC BY-SA 4.0, via Wikimedia Commons.
After years of decline and closure, a preservation campaign restored the building, and it reopened in 1992. Today it continues to serve as a museum, library, gallery, theater and cultural center. Because access and programming can vary, check the San Carlos Institute's official website before visiting.
José Martí and Key West's Role in Cuban Independence
Key West was more than a refuge for Cuban exiles. It became an important center of the independence movement. Poet, journalist and revolutionary leader José Martí visited the island repeatedly, addressing supporters, building unity among exile groups and raising money for the effort to end Spanish colonial rule in Cuba.
Martí spoke at the San Carlos Institute and other gathering places throughout the Cuban community. Cigar workers famously supported the cause with regular contributions from their wages, while clubs and newspapers helped circulate political ideas.
Photo Credit: Keys Weekly, Bruce Neff
One surviving landmark is the former home of cigar manufacturer Teodoro Pérez at 1125 Duval Street. Martí addressed supporters from its balcony, and the property became known as La Terraza de Martí—Martí's Terrace. The shortened name, La Te Da, remains familiar in Key West today. Visitors can appreciate the historic exterior and marker while remembering that the property is now an operating hotel and entertainment venue.
Cuban Art, Architecture and Everyday Culture
Key West's built environment reflects many influences, including Cuban, Bahamian, Caribbean, Spanish and American traditions. The San Carlos Institute, former cigar factories, workers' cottages and historic homes help tell the story of communities that adapted their surroundings to island life.
The Cuban presence also survives through visual art, music, family traditions and language. Spanish names and phrases remain part of the island's vocabulary, while galleries and cultural programs continue to interpret the relationship between Key West and Cuba.
Artwork Photo Credit: The Gallery on Greene / Silvia Rivero.
Cuban heritage exists within Key West's wider multicultural identity rather than apart from it. A walk through Old Town and nearby Bahama Village reveals how Cuban, Bahamian and other Caribbean communities contributed different threads to the island's character.
Taste Key West's Cuban Heritage
Food may be the easiest—and most enjoyable—way to experience Key West's Cuban influence. Start with café cubano or café con leche, then look for dishes such as ropa vieja, roast pork seasoned with citrus and garlic, picadillo, black beans and rice, fried plantains, yuca and flan.
Several longtime and locally recognized businesses make it easy to build Cuban flavors into a day on the island. El Mesón de Pepe serves Cuban food near Mallory Square, El Siboney is known for traditional, homestyle dishes, and Cuban Coffee Queen offers coffee and casual Cuban favorites at multiple Key West locations.
Menus, locations and hours can change, so check directly with each business before planning a meal. Wherever you stop, remember that Cuban cuisine in Key West is not simply a visitor attraction. It is part of the island's everyday life.
How to Explore Cuban Heritage in One Day
Begin Near the Historic Seaport
From the Key West Express terminal, walk toward Old Town and begin with Cuban coffee or breakfast. The short distance between the waterfront and the historic district helps put the island's maritime relationship with Cuba into perspective.
Visit the San Carlos Institute
Continue to 516 Duval Street to see the building that served generations of Cuban residents as a school and cultural center. Even when the interior is not open, the exterior is an important Old Town landmark.
Follow the Martí and Cigar-Era Story
Walk farther along Duval Street toward the former Terraza de Martí, then continue east to see the historic E.H. Gato Cigar Factory building on Simonton Street. The building is now used by Monroe County, so view it as a historic exterior rather than assuming it operates as a visitor attraction.
Add a Museum and a Cuban Meal
The Key West Museum of Art & History at the Custom House provides broader context for the people and industries that shaped the city. Finish with a Cuban meal, sandwich or coffee before returning to the waterfront.
A Living Heritage, Not Just a Historic Chapter
Key West's Cuban heritage cannot be reduced to cigars, one political movement or a handful of buildings. It lives in family histories, food traditions, music, art, language and the island's habit of looking south across the Florida Straits as naturally as it looks north toward the mainland.
Traveling aboard Key West Express offers a fitting way to begin that story. Instead of spending the day behind the wheel, you cross the Gulf and arrive close to Old Town, ready to explore on foot. When you are ready, review current travel information and book your Key West Express trip.
Hero Image Photo Credit: Alvin Jewett Johnson, Public domain, via Wikimedia Commons.
