The trip, which follows more than one year of thawing relations between the two countries, happens as Cuba is experiencing a spike in tourism that is putting a lot of strain on its hotels.
To make room for the president and his entourage, many hotels have no choice but to move their guests from Havana to the capital's outskirts, near the beach.
While this might sound as a pleasant change of scenery, it is actually putting many Americans who are visiting the island in a difficult position: US law, in fact, forbids citizens from traveling to Cuba for tourism.
Only cultural exchanges or study trips are allowed — to a certain extent. This explains why most American citizens on the island generally opt for staying in Havana — which is a culturally rich site but has a rocky waterfront and not a lot of touristy amenities.
US #travel to #Cuba up 50% this year https://t.co/9HiFqC4rVM Join @CubaExpert https://t.co/IRXmMPvwgE pic.twitter.com/lPAODUKHUS
— Christopher P Baker (@CubaExpert) December 17, 2015
As strange as it may seem, then, an American sipping a cocktail on Cuba's wonderful sandy beaches would be probably committing a crime.
"The Cuban government is clearing out Havana hotels and sending visiting US groups to [the seafront resort of] Varadero Beach for a long weekend," said Collin Laverty, president of Cuban Educational Travel, which organizes authorized US travel groups.
"Tourism will be hard to avoid for a few days as US visitors are surrounded by white sand, turquoise water and all you can eat and drink bars and buffets… But we will try."
The presence of American visitors on the island is a result of the US-Cuba rapprochement, brokered by Pope Francis and announced by Obama and Cuban President Raul Castro in December 2014.
Over $14 billion worth of blockade/sanctions fines have now been under Obama (2009-2016) https://t.co/nmlKZxuhxh pic.twitter.com/UoZ8qtJqzX
— CubaSolidarity (@CubaSolidarity) March 1, 2016
While Obama has lifted some travel restrictions and trade barriers on Cuban goods, he cannot single-handedly remove the Cold War-era embargo and the tourism ban, which are still in place.
Only Congress, currently controlled by the Republican party, has the power to make that decision.