But the wheels didn't even hit the ground before the warming ties initiated by President Barack Obama were thrown into doubt by President-elect Donald Trump, who has tweeted that he might "terminate" the detente.
The travel industry, among others, hopes otherwise.
Passengers from Miami, wearing straw hats provided by American Airlines with the word "Cuba" on the back, were greeted with welcome signs in various languages, but no music.
The landing "was very emotional for me," said Jonathan Gonzalez, 31, a Cuban-American born in Miami who said it was his third time visiting the island.
For decades, people thought it would take the death of Castro to open up travel to Cuba.
In reality, restrictions on travel from the US had already eased since Obama lifted some rules last year by executive order.
Several airlines began routes to other Cuban cities earlier this year. Later yesterday, a JetBlue flight arrived in Havana from New York.
Despite the relaxing of travel restrictions, going to Cuba isn't exactly like hopping a flight to another Caribbean destination. Pure tourism remains illegal under US regulations that allow 12 categories of travel to Cuba.
They include religious and sports activities and educational travel promoting "people-to-people" contact which is the clause most United States citizens travel under.
For Americans without family ties to Cuba, the most popular form of travel had been on tightly focused educational trips organised in conjunction with the Cuban government.
What happens after Trump's inauguration in January is murkier.
"If Cuba is unwilling to make a better deal for the Cuban people, the Cuban/American people and the US as a whole, I will terminate deal," Trump tweeted yesterday.
Some in the travel industry remain hopeful that Washington will keep its Cuba policies intact and that Havana won't react by shutting off travel.
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