Before Key West became famous for sunset celebrations, colorful characters and tropical escapes, it was known for something else: cigars. In the late 1800s, Cuban tobacco, Cuban craftsmanship and Key West's location just 90 miles from Cuba helped turn the island into one of the nation's most important cigar-manufacturing centers.
That history is still woven into the streets of Old Town. Travelers arriving aboard Key West Express step ashore near the Historic Seaport, within easy reach of neighborhoods and landmarks shaped by the island's close relationship with Cuba.
Tobacco was cultivated in the Americas long before Europeans arrived. After Spanish explorers encountered it, tobacco spread to Europe, and cigar smoking became increasingly fashionable during the 19th century. Cuba's climate, soil and generations of agricultural knowledge helped its tobacco develop an international reputation for quality.
A traditional premium cigar is more complex than a simple roll of tobacco. Its filler provides much of the flavor and strength, a binder holds that filler together, and a carefully selected wrapper forms the smooth outer layer. After harvesting, tobacco leaves are cured, fermented, sorted and aged before a skilled cigar maker—or torcedor—shapes the finished cigar by hand.
Photo Credit: Adam Jones Adam63, CC BY-SA 3.0, via Wikimedia Commons.
Key West offered an unusual combination of advantages. It was close enough to Cuba for tobacco and workers to travel across the Florida Straits, while its warm, humid air helped keep tobacco leaves pliable during production. The island was also an American port, which became especially valuable after an 1857 tariff made finished cigars imported from Cuba more expensive.
Factory owners could bring Cuban-grown tobacco to Key West and employ experienced Cuban cigar makers to produce what became known as “clear Havana” cigars. The term did not mean the cigars were manufactured in Havana. It meant they were made in the United States entirely from Cuban tobacco.
In 1867, Samuel Seidenberg established Key West's first clear Havana cigar factory. Others quickly followed, and the industry grew at a remarkable pace.
By 1873, 15 cigar factories employed more than 1,200 workers in Key West. Just three years later, 29 factories were producing approximately 62 million cigars annually. The industry attracted thousands of immigrants—particularly Cubans—and helped Key West grow into Florida's largest and wealthiest city by 1890.
At its height, Key West was producing more than 100 million hand-rolled cigars a year. Large factories stood alongside smaller workshops, filling the air with the scent of tobacco and creating an economy that reached far beyond the rolling table. Printers made cigar-box labels, carpenters built boxes and buildings, merchants served workers and ships carried raw materials and finished products.
Photo Credit: Alexander Klink, CC BY 4.0, via Wikimedia Commons.
The success of a cigar factory depended on the hands and judgment of its workers. Torcedores selected, trimmed and rolled leaves with techniques learned through years of practice. Because the work required concentration, many factories employed readers known as lectores, who read newspapers, novels and political commentary aloud while employees worked.
Cigar workers did more than support an industry. They built homes, businesses, mutual-aid societies and cultural institutions that strengthened Key West's Cuban community. Factories also became gathering places for conversations about Cuban independence, and the island played an important role in fundraising and organizing for that movement.
One prominent manufacturer was Eduardo H. Gato, who founded what became Key West's largest cigar factory in 1876. His operation and the surrounding worker community known as Gatoville became enduring symbols of the era. The surviving E.H. Gato building at 1100 Simonton Street dates to 1916, replacing an earlier wooden factory that burned.
Key West's dominance did not last forever. Labor disputes, transportation challenges and the search for more room encouraged some manufacturers to relocate. Vicente Martínez Ybor, one of the best-known cigar producers associated with Key West, moved his operation to an area northeast of Tampa in 1885. The community that developed around the new factories became Ybor City and was incorporated into Tampa in 1887.
Tampa's rail connections and available land helped it become a powerful competitor. Later, inexpensive machine-made cigars and the economic strain of the Great Depression accelerated the decline of hand-rolled cigar manufacturing in Key West. The island's cigar economy faded, but the people, architecture and cultural traditions it brought together remained.
The factories may no longer define the local economy, but visitors can still find traces of the cigar era throughout Key West. The historic E.H. Gato building stands on Simonton Street, and the surrounding streets reveal how closely industry, housing and community life once fit together on the small island.
For a broader understanding of the people and events that shaped the city, visit the Key West Museum of Art & History at the Custom House. You can also use our guide to the secrets of historic Key West to add more meaningful stops to your walk through Old Town.
This cigar story is one chapter in a much larger relationship between the two islands. Our separate look at how Key West embraces its Cuban heritage explores that wider cultural connection through food, architecture, traditions and community life.
A hand-rolled cigar sold in Key West is not necessarily a Cuban cigar. Local cigar shops may offer cigars made in Cuban styles or by cigar makers with Cuban heritage, but a true Cuban-origin cigar contains tobacco from Cuba.
Under current U.S. rules, travelers may not import Cuban-origin tobacco products into the United States, even when they were purchased in another country or intended for personal use.
Key West's cigar history is a story of geography, migration, skilled labor and cultural exchange. Knowing it changes the way you see the island: an old factory becomes evidence of a booming industry, a neighborhood reveals the lives of its workers, and the short distance to Cuba feels central rather than incidental.
Make the journey part of the experience aboard Key West Express. Leave the long drive behind, relax during the trip across the Gulf and arrive close to the historic districts where this story unfolded. Review current sailing information and book your Key West Express trip when you are ready to explore.
Hero Image Photo Credit: kuhnmi, CC BY 2.0, via Wikimedia Commons.