The visit comes just 15 months after the announcement that the U.S. and Cuba would be restoring diplomatic ties.
As Air Force One was still on the runway, Obama tweeted that he was "looking forward to meeting and hearing directly from the Cuban people."
There was no pomp and circumstance as the first family descended the steps onto Cuban soil, and they were not greeted by Castro in person, as he did when Pope Francis visited the country last September. Instead the Obamas were greeted by high level members in the Cuban Ministry of Foreign Affairs and the U.S. and Cuban Embassies.
Obama is being joined by a massive U.S. delegation during his visit; 39 members of Congress including five Republicans will be following his movements.
In his first stop, President Obama visited U.S. Embassy staff at a local hotel, where he called his visit "a historic opportunity."
"Back in 1928, President Coolidge came on a battleship, it took him three days to get here," Obama said. "It only took me three hours."