The Fort Lauderdale, Florida, to Santa Clara, Cuba, flight is the latest symbol of the thawing of relations between the former Cold War adversaries, who restored diplomatic ties in 2015.
Until now, Santa Clara was most famous for being the site of the tomb of Ernesto "Che" Guevara, the Argentine revolutionary who fought alongside Fidel Castro and was later killed with the help of the CIA while leading an insurrection in Bolivia.
Soon, up to a maximum of 110 daily flights operated by US carriers are due to begin flying to the communist-run island, according to the US Department of Transportation.
The department later Wednesday that eight carriers will begin scheduled flights to Cuba's capital city Havana as early as the fall. Those carriers are: Alaska Airlines, American Airlines, Delta Air Lines, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines and United Airlines. The flights will provide service to Havana from Atlanta; Charlotte, North Carolina; Fort Lauderdale; Houston; Los Angeles; Miami; Newark, New Jersey; New York City; Orlando, Florida; and Tampa, Florida, the department said.
"Today's actions are the result of months of work by airlines, cities, the US government, and many others toward delivering on President Obama's promise to reengage with Cuba," said US Transportation Secretary Anthony Foxx. "Transportation has a unique role in this historic initiative and we look forward to the benefits these new services will provide to those eligible for Cuba travel."
Travel ban remains in effect
Although the Obama administration has eased restrictions on travel to Cuba, there is still a travel ban for Americans visiting the island.
Tourism to Cuba is still illegal, but there are now 12 categories of "authorized travel."
Before US citizens can board flights to Cuba, they will need to sign an affidavit swearing their travel falls within the permitted categories, including educational, religious and humanitarian reasons.
With the relaxing of the travel ban, Cuba has seen a spike in US visitors: about 93,000, or nearly double from the year before, according to Cuban tourism officials.
Despite the increase, Cuban officials say the embargo, or the "blockade" as they refer to US sanctions, must be lifted before there is full freedom of travel between the two countries.
"This process of establishing regular flights is a positive step," said Eduardo Rodríguez, the Cuban Vice Minister of Transportation at a news conference on Monday in Havana."Although the restrictions of the blockade remain, which among other things impede United States citizens from traveling to our country as tourists."
Rodríguez said Foxx would travel to the island on Wednesday to mark the historic occasion of the first direct commercial flight.
More than 50 years of no commercial flights
Until Fidel Castro's revolution in 1959, Cuba had been a favorite vacation spot for Americans in the Caribbean. But in 1961, after Castro declared his government to be in the Socialist camp, diplomatic relations were severed and direct commercial fight service disrupted.
"Castro cracks down on flights from Cuba," reads a UPI wire service headline from the era.
During the 1962 Cuban missile crisis, US carriers were briefly banned from flying over the island and the Cuban military shot down a U2 spy plane, killing the pilot.
For the decades that followed, the only US aircraft that traveled to the island were the result of frequent hijackings.
In 2001, a change in US regulations allowed Cuban Americans to visit family on the island and for charter flights to begin to travel between the two countries.
Cuban officials say that since then they have coordinated closely with their American counterparts and are ready for the US carriers to return.
"In relation to aviation security, we have been working with the US government for about 15 years. This isn't new," said Alfredo Cordero, the president of the Cuban Civil Aviation Institute. "Cuba gives the maximum attention to this aspect of aviation security and we have achieved the training of personnel and the necessary resources to obtain the security that's required by the International Civil Aviation Organizations."
Concerns about security
But not everyone is celebrating the resumed flight service.
Rep. John Katko, a New York Republican, said the flights pose a risk to US security.
"TSA has not come close to doing a thorough security assessment of the airports in Cuba," he said, referring the Transportation Security Administration.
Katko and two other lawmakers introduced legislation earlier this summer in an effort to block the flights to Cuba until they felt certain Cuban airport security could effectively prevent terrorists from targeting US-bound flights.
They were unsuccessful in stopping the flights, but Katko told CNN he remains concerned about how the Cuban Civil Aviation authority will prevent insider threats, meaning airport workers who may conspire to target a US-bound aircraft.
"I just think its dangerous and, again, I'm not saying anything bad is going to happen, but we just got to do our due diligence and we are just not doing it," he said.
The TSA said the agency has inspected Cuban airports and found they comply with international standards.
In an email to CNN, agency spokesman Michael England said, "TSA has assessed eight of the ten airports and will complete the final two before flights commence at those locations."
When asked about the lack of high-tech screening machines, England responded, "Technology is only one element of a security system that is multi-layered and involves people, processes and technology. TSA has sent teams of TSA inspectors on a regular basis to Cuba to assess airports currently operating as last points of departure to ensure compliance with international standards" set out by the International aviation arm of the United Nations, ICAO.
Over the summer, Cuban airports adopted US security requirements like requiring passengers traveling to the US to remove their shoes and leave liquids at checkpoints.
The agency said it would not say how Cuban airport workers would be vetted because "releasing this information publicly could pose a threat to aviation security."
For many Americans, though, the immediate concern is not security but seeing Cuba before the island emerges from the Cold War time warp of the last 50 years.
"Our friends had been here and said, 'Why don't you come to Cuba before it's too Westernized?'" said Gerry Hall, a New York educator who joined a "people-to-people" tour of the island in August.
"We wanted to come before you see McDonald's and Walmart and other US companies in Cuba," she added.