A group of 38 business leaders and politicians from Tampa flew to Cuba in late May. Tourist visas forbid them from any official meetings. But there was no mistaking that the trip was about promoting Tampa as Cuba’s future trading partner.

On the last night of the five-day trip, members of the delegation gathered at the bar at the Hotel Nacional de Cuba to watch the sun set over the Florida Straits and sip 7-year-old rum.

Vince Cassidy was among the Tampa delegation. He went with a singular purpose: Someday Cuba will open up to U.S. investors. Land purchases will be a mess. Title companies — like the one Cassidy owns in Tampa — will be needed to research convoluted sales histories.

As Cassidy sipped drinks at the hotel bar, he kept thinking: “We have a foreign country 90 miles away from our shores. We’re not doing business with them right now. Imagine if we were.”

Quietly at first, and now quite publicly, the city of Tampa has courted Cuba in hopes of becoming its future trading partner. Business owners talk of how to expand into Cuba. Politicians make trips there and have come out against the embargo.

Tampa’s efforts began in 2002 with a visit from its mayor. A city councilwoman followed with multiple trips over the past decade, and in May the chamber organized a group of 38 politicians and business leaders.

Tampa politicians talk of expanding direct flights to Havana. They want to be home to cruise ships that call to Cuban cities. And they imagine the port of Tampa becoming the main hub of goods heading to the island once the embargo is lifted.

José Gabilondo, head of the Cuban Research Institute at Florida International University, said Tampa city leaders talk of exploiting Miami’s reluctance to plan for Cuban trade.

“Ironically, Miami may be the only major city in Florida that’s not actively preparing for more engagement with Cuba,” he said.

Tampa is making a mistake, said Andy Gomez, a Cuba expert and former senior fellow at University of Miami’s Institute for Cuban and Cuban-American Studies. The country’s crumbling infrastructure can’t support business on a large scale, and its legal system is so corrupt that companies have no recourse when debts go unpaid, he said.

“I don’t know about you, but I don’t want to invest in Cuba,” Gomez said. “Why would Tampa take that risk with a country that’s in shambles?”

Miami-Dade Commissioner Javier Souto compared Tampa’s plans to trade with Cuba to countries that have ignored the U.S. embargo. “They don’t care about human rights, they don’t care about freedom of expression, they don’t care about any of that, these other countries of the world,” he said. “They only care about money.”

Patrick Manteiga, meanwhile, talks about the jobs Tampa will add. He’s publisher of La Gaceta, the Cuban-focused newspaper in Tampa. His grandfather founded the paper in 1922 after spending years as a reader in the Ybor City cigar factories, shouting out the day’s stories to the workers. Manteiga said he circulates 18,000 copies a week in 44 states.

Manteiga has published editorials in favor of lifting the embargo. He has traveled to Cuba. He met with Fidel Castro and had him sign a photo — the photo shows Manteiga’s grandfather sitting with Castro at a table overflowing with money raised for the revolution.