From cigars to Hemingway, rum-drinks to deep-sea ﬁshing, Cuba and Key West have a history and future that are closely aligned. Ponce de Leon was the ﬁrst European to discover the much smaller island in 1521. Soon after, Spanish ﬁshermen named the island Cayo Hueso (Bone Key), ﬁnding the island littered with bones from an indigenous battleﬁeld or burial ground. Key West remained part of the Spanish realm for over 250 years until Great Britain took control of Florida in 1763, at which time the existing community of Spanish and Native Americans moved to Havana.
By 1876, Key West was a bustling center of trade, with Cuban cigar rolling its primary industry—exporting more than 100 million cigars per year from the small island city. Half of the residents were Cuban or of Cuban descent, including many local politicians.
On January 3rd, 1892, Jose Martí addressed the people of Key West from the balcony of the San Carlos Institute Southernmost point in the U.S.A. on Duval Street. His speech united the various Cuban exile groups, and lead, on April the same year, to the establishment of the Partido Revolucionario Cubano that encompassed the interests and characteristics of the diﬀerent groups of immigrants and members of Cuban society elements. It would also provide a program to prepare the new war against Spanish colonial rule, in addition to the urgency to give coherence and unity to all independence eﬀorts.
Ernest Hemingway's love for the sea —and in particular the Florida Straits— led him to acquire homes in both Key West and Cuba, writing novels set in both locations with colorful characters traveling regularly the hundred miles of water between Key West and Havana. With the advent of air-travel, tourism between Key West and Cuba became a day-trip, a leisurely ﬂight of less than an hour.
In 1956 the West India Fruit and Steamship Company launched regular car ferry service aboard the S/S City of Havana. The largest ship operating from Florida to Cuba, the ferry held 500 passengers, 125 cars, and sported air-conditioned first class cabins. The seven hour trip departed from Stock Island (Key West) three days a week, making the return trip the following day. Regular travel between the two islands was at its apex.
In recent decades, direct travel between both cities has been at its lowest in 200 years. Yet, at the present there are eﬀorts being made to reconnect these islands in the stream. One such eﬀort is being led by Stock Island Marina Village in Key West. With the largest deep water marina in the Florida Keys —just 100 miles from Havana— the Marina Village is investing in new infrastructure and services to accommodate international yachts and cruisers as they make way south to the pristine waters of Cuba. Perhaps the coming years will see these islands connected.