Mayor-elect Maynard Jackson boarded a flight to Havana in 1989 with one purpose in mind: Securing the votes needed for Atlanta to host the 1996 Olympics.

The visit came three decades into Castro’s Communist regime. Though the Caribbean country was fully feeling the effects of a rigid economic embargo imposed by the United States, Cuba was also in the midst of planning for the Pan American Games. The event’s organizing committee consisted of big wigs from around the world, many of whom would also decide Atlanta’s Olympic fate.

More than 25 years later, Mayor Kasim Reed, too, is set to travel to the island nation. But, with the United States and Cuba on the precipice of a new era, he isn’t trying to solely court powerful people who are visiting for business or pleasure. He’s courting Cuba itself.

The mayor has said he views this five-day trip as an opportunity to pitch Atlanta as an alternative to Miami for future trade. It’s a goal that Reed set long before President Barack Obama announced efforts to re-establish commercial and diplomatic relations with the country.

Reed is also surely hoping to be among the first crop of leaders from major U.S. cities to make overtures to the island seemingly trapped in time, yet poised for dramatic change. The White House has taken sweeping actions to loosen some existing travel and trade restrictions, though it would take an act of Congress to lift a long-standing trade embargo.

American businesses currently have limited opportunities there, but Reed said he’s exploring what’s possible now and in the years to come.

“I think that Atlanta and Georgia have a unique opportunity with Cuba to be first to the future,” said Reed, who will fly to Havana on Saturday with a group of academics, business professionals and diplomats with the World Affairs Council of Atlanta. Atlanta Councilman Kwanza Hall is also attending.

“We really have a moment to position Georgia and Atlanta as the business partner for Cuba because we don’t have the political drag, if you will, that Florida has,” said Reed, referring to Miami’s politically active Cuban-exile population. “I’m going to Cuba to start getting to know people and to send a clear message that we have a deep interest in a long-term relationship.”

Reed is traveling to Havana on a highly stylized “people to people” trip allowed under current U.S. travel regulations. With an economy that has faltered under Communist control, the Cuban government has turned back to tourism as a means of revenue. Americans are allowed to meet with selected — and likely coached — Cuban scholars, business folks and diplomats.

It will be the first visit by an Atlanta mayor since Jackson, who was accompanied in 1989 by Olympic committee executives Billy Payne and Horace Sibley, recalls Angelo Fuster, who served as communications director for Jackson back then.

Jackson made a second visit to Havana in 1991 for the 11th Pan American Games. That historic event drew thousands of Americans, including Ted Turner and Jane Fonda, to Cuba’s shores.

Fuster still has photos of the mayor and Castro, clad in his famous olive green military uniform, taken during each of their trips. The images show a smiling Castro, far different than the feared leader whose policies prompted Fuster and his sister to flee the island in 1961.

Former mayor Shirley Franklin also visited the country in the mid-1980s while serving as chief operating officer for then-mayor Andrew Young. The trip, Fuster recalls, was arranged by the city of Havana as the Cuban government tried to improve relations with the United States.

The group of a dozen or so city officials met with Cuban airport officials about direct flights from Atlanta to Havana and had similar meetings with other representatives of the Cuban government, Fuster said.

“In those days, the Cuban government was eager to show their country to public officials in the U.S. because there was a sense that relations were slowly thawing and such encounters would help,” he recalled.

Christina Abreu, a history professor who specializes in Latin America at Georgia Southern University, sees significance in the return of an Atlanta leader at this time. And she agrees that Georgia and its capitol city have an opportunity to develop trade with a country that largely sees America through the prism of Miami.

Data from the 2010 U.S. Census show that Florida is home to more than 1.2 million Cubans, the majority who fled Cuba as a result of Castro’s brutal regime and are now concentrated in Miami. As a result, they hold considerable sway over the direction of U.S. politics and policies toward their native country.

By comparison, Georgia is home to roughly 25,000 Cubans, according to data from the same year.

“There’s a long history between Miami and Havana, one that is very tense, very sordid,” Abreu said.

Atlanta has an advantage, she said, because Reed can "position himself by saying my interests aren't political, they're economic, and approach it with a clean slate."

Because of exceptions to the embargo, which allow for the sale of agricultural and pharmaceutical products, Georgia has well-established trade with Cuba. Poultry is by far Georgia’s top export there, followed by animal feed products, prepared meat and seafood products.

Many eye future opportunities in the medical device, automotive, tourism, telecommunications and technology sectors, and hope that Delta will resume direct charter flights from Atlanta to Havana.

But Abreu, like many historians and diplomats, cautions that despite pledges from the White House to work toward thawing relations, the two countries have far to go before establishing trade in earnest. Many say that relationship took a significant step forward, however, when the U.S. removed Cuba from its terror watch list last month.

“As with anything between the U.S and Cuba, things are very slow,” Abreu said. “Look at the history of relations since the Revolution. To think that any change or any opening of relations will be quick is a misunderstanding of the history of how these things kind of work.”