The flights, however, won't be bringing hordes of New Yorkers for glamorous weekends of rum, beaches and cigars that were notorious in pre-Castro Cuba and immortalized in films such as Weekend in Havana.
Only researchers, journalists, Cuban-Americans visiting relatives and other individuals eligible for U.S. visas will be allowed to travel on the Marazul Charters flights, which will be inaugurated Friday night at New York's John F. Kennedy airport.
Marazul has hired El Salvador's TACA airlines to take 150 passengers on the nearly four-hour flights, which cost $629 round-trip. Most of the first flight's passengers are Cuban-Americans from New Jersey, although about 30 people are traveling to attend a film festival in Cuba.
Marazul founder Francisco Aruca, who will be on board, says he hopes the new weekly service will help improve relations between the United States and the communist island.
"I think it's a reflection of the times," Aruca, 59, said in an interview from his headquarters in Miami. "I do believe that slowly, we are moving in the right direction in terms of normalizing things in terms of Cuba."
Americans have been barred from legally traveling to Cuba as tourists because of an embargo imposed on the island in the early 1960s. The embargo has been maintained since then in a bid to promote democratic change.
Miami-based companies, however, have organized regular charter service to the island for years, mostly to cater to Cuban exiles eager to visit relatives and bring them medicine and other items unavailable there.
The Clinton administration halted the flights in March 1996 after Cuba shot down two civilian planes. The planes, which belonged to a Miami-based exile group, searched the Florida Straits for people trying to flee Cuba on rafts but also had flown over Havana to drop political leaflets.
The Treasury Department allowed Miami-Havana charter flights to resume in June of last year, after Pope John Paul II visited Cuba and the U.S. administration unveiled a program to increase humanitarian aid to the country.
Ninoska Perez, spokeswoman for the anti-Castro Cuban American National Foundation, said the organization supports humanitarian aid to Cuba. But she said the flights are yet another indication that the U.S. administration is giving President Fidel Castro concessions he doesn't deserve.
"The conditions are just the same. Dissidents are being arrested," she said. "What has the Cuban government done to merit direct flights to Cuba?"
But Aruca, whose Miami offices were bombed by suspected anti-Castro activists in 1989, said the flights show that American popular opinion is beginning to turn against the policy of isolating Cuba. He said h decided to pursue the New York-Havana flights to cater to the Cuban-American community in New Jersey - one of the largest in the United States outside of Miami - and perhaps to one day have American tourists visit the island.
Written By Nicole Winfield