Thirty-five years ago, Joe Doss helped load 473 political prisoners on a World War II-era ship bound for the United States.

Doss, then an Episcopal priest in New Orleans, had spent two weeks in Cuba organizing the rescue as part of a church mission authorized by both nations’ governments. The vessel, dubbed “God’s Mercy,” was part of the Mariel boatlift, in which 125,000 Cubans unwanted by Fidel Castro’s government were allowed to flee the country.

On Saturday, Doss, 71, made his first return to Cuba since then, heading an 80-person delegation of south Louisiana business, education and civic leaders.

“I’m expecting to see a very different place,” Doss said before setting out. “Then, it was tyrannical. There was no good food. Cubans were afraid to talk to us. It was not a fun trip. Now, I’m expecting to see a country that’s opening up in many ways.”

Doss and the others attending the Cuba Hoy Conference made what is believed to be the first direct flight from New Orleans to Havana in more than 50 years — an especially noteworthy event because the two cities had close economic and cultural ties until the aftermath of the 1959 Cuban revolution that brought Castro to power.

The delegation is the first one to visit Cuba from Louisiana since President Barack Obama and Cuban President Raúl Castro, Fidel’s brother, agreed in December to begin normalizing relations between the countries — relations that have been stuck in a Cold War embrace dating from the Eisenhower and Kennedy administrations.

The two countries do not have diplomatic relations, and since 1962, the United States has enforced a trade embargo on most goods sent to Cuba. That embargo remains in place.

Before the 1959 revolution and the exodus of Cubans to Miami and elsewhere, New Orleans served as a gateway to the Caribbean island. The weeklong trip is an attempt to position Louisiana to be a player as Cuba transitions from the communist regime of Fidel Castro, who ceded official power to his brother nine years ago, to an uncertain future.

Kevin Berken, a rice farmer in Acadiana who chairs the Louisiana Rice Promotion Board, said Cuba was a major importer of Louisiana rice before the U.S. embargo. Today, Cuba imports its rice from Vietnam. Getting rice from Louisiana would take only two days, said Berken, who is not making the trip.

“Other Gulf Coast states aren’t sitting around,” said Randy Haynie, a prominent Baton Rouge lobbyist whose grandmother was Cuban and who is on the trip. “It’s going to be a competition. I see wonderful opportunities for business and tourism.”

To that end, the delegation will hold several sessions with the University of Havana’s law school, with an eye toward analyzing how American citizens can take advantage of the fact that they now can own property in Cuba.

Mary Dumestre, a longtime attorney at the New Orleans law firm of Stone Pigman Walther Wittmann, wants to get a better handle on such basic questions as: How do you transfer property to private ownership in a country where the government has nominally owned everything?

“How do they deal with contracts?” Dumestre asked. “How are contracts enforced? How do you get property, title or liability insurance in Cuba?”

The trip was organized by Doss’ progressive religious group, At the Threshold, and the International Cuba Society, a New Orleans-based group headed by attorney Romualdo “Romi” Gonzalez.

Not everyone is pleased that the trip is taking place.

“It’s a complete waste of time,” said George Fowler III, a New Orleans lawyer who was born in Cuba and is the general counsel for the conservative Cuban American National Foundation, based in Miami. “There’s nothing to do in Cuba absent the embargo being lifted. And lifting the embargo requires congressional approval. That won’t happen with Obama as president.”

Ana Lopez, the director of Tulane University’s Cuban and Caribbean Studies Institute, sees benefits to traveling now. “What has begun to happen is the chipping away of the embargo,” she said. More and more Americans are traveling to Cuba, and Obama already has liberalized some trade and travel rules.

“You can’t imagine what will happen in the future if you don’t get a foot on the ground,” said Lopez, a Cuban native who is on the trip.

Wanting to get a foot on the ground helps explain why Guy Williams, the chief executive officer of New Orleans-based Gulf Coast Bank & Trust, signed up for the trip. “We do business in Central America,” Williams said. “We would love to do business in Cuba as well. Hopefully, Cuba can turn back into a democracy with civil rights and a market economy.”

Pres Kabacoff, a pioneer in redeveloping the Warehouse District and now the Bywater neighborhood in New Orleans, will give a presentation attended by Cuban officials on how to redevelop old neighborhoods. That could have special resonance because Old Havana looks and feels like the French Quarter but remains rundown.

“I want to tell them that development takes place through private-public partnerships,” Kabacoff said. “The government needs to fill the gaps to allow the commercial developer to get it done. How that plays in a communist country, I don’t know.”