TAMPA, Fla. — Decades before Miami danced to a Cuban rhythm, Tampa’s Ybor City grew up and got rich to the sounds of Cuban-inflected Spanish as thousands of workers rolled cigars by day and plotted the island’s independence from Spain by night.

The city was America’s first touchstone for Cubans from the island. José Martí, the poet and the hero of Cuban independence, visited often during the 1890s to plan insurrection and to raise money from the successful cigar barons and their employees. A young Fidel Castro retraced Martí’s steps in the 1950s, hoping for a similar infusion of money and inspiration to boost his own revolution. Later on, exiles and former Cuban political prisoners streamed in, escaping Mr. Castro’s Communist grip.

Today, Tampa sees itself as pivotal to Cuba once again: The city is taking the lead in the Obama administration’s effort to rekindle diplomatic ties to Cuba, a move that runs counter to the anti-engagement orthodoxy of Miami and Florida’s state government.

In fostering closer ties to Cuba — a stance some here embraced long before President Obama’s December announcement — Tampa is positioning itself to one day reap the economic benefits of helping rebuild the crumbling country. Tampa’s port allows for a straight shot to Havana’s, giving it a major advantage if the United States lifts its economic embargo. Beyond that, city officials want to begin mending the historical kinship and once-powerful economic links between Cuba and Tampa that reach back more than six generations.