Obama's arrival on Sunday afternoon was eagerly anticipated in the capital Havana, according to The Associated Press.
"Que bola Cuba?" Obama wrote on his Twitter on landing, using Cuban slang to ask what's going on. "Just touched down here, looking forward to meeting and hearing directly from the Cuban people."
During his two-day trip, Obama is expected to meet with his Cuban counterpart Raul Castro and representatives of the private sector.
The US president will also deliver a historic speech in Havana in an effort to establish a new relationship between the Cold War-era foes.
US House Minority Leader Nancy Pelosi and Senators Patrick Leahy, Dick Durbin and Congressman Jeff Flake also joined the president aboard Air Force One along with First Lady Michelle Obama, daughters Malia and Sasha Obama.
“I’ll travel to Cuba to advance our progress and efforts that can improve the lives of the Cuban people,” Obama tweeted last month. “We still have differences with the Cuban government that I will raise directly. America will always stand for human rights around the world.”
In December 2014, Obama announced the US would normalize relations with Cuba.
The two countries have reopened embassies in Washington and Havana, and restored commercial air travel.
The newly amended sanctions regulations, however, fall short of ending the embargo which has been in place for more than 55 years.
Last week, however, the United States announced that it would further ease travel and trade regulations on Cuba.
The new rules, announced by the US Treasury and Commerce Departments on Tuesday, will allow Americans to travel to Cuba as individuals, and give Cubans more access to US banks.
The changes went into effect on Wednesday as part of the broader easing of diplomatic relations between the two former Cold War adversaries.
Cubans will now be able to open US bank accounts, and those who live in the US can earn a salary or compensation.
Previously, Americans could visit Cuba only in group tours, but the new changes will allow them to take “people to people” educational trips.
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