US President has shaken hands with Venezuela's President, a bitter foe of the former Washington administration.
After several days of the US and Cuba trading warm words that have hinted at a détente after a half century of hostility, Mr Obama said that he was seeking "a new beginning" with Havana.
Asked what he had said to Mr Chavez, Mr Obama replied with a smile: "I said como estas" (How are you).
Mr Obama meanwhile made his diplomatic overtures to Cuba as he joined 33 other leaders of Western Hemisphere states at the Organisation of American States summit in Port of Spain on Friday - only Cuba is not represented after being thrown out in 1962.
Obama said: "The US seeks a new beginning with Cuba. I know there is a longer journey that must be travelled to overcome decades of mistrust, but there are critical steps we can take toward a new day."
His comments came a day after Cuba's President Raúl Castro said that Cuba was ready to discuss "human rights, freedom of the press, political prisoners – everything". Significantly, he also acknowledged that the regime "could be wrong".
Obama announced earlier in the week that the US was easing restrictions on travel and remittances for Cuban-Americans and challenged Mr Castro to make concessions of his own.
In his speech in Trinidad, Obama renewed his promise for his administration to engage with the Cuban government "on a wide range of issues", including human rights, free speech, democratic reform, drugs, immigration and the economy.
"Let me be clear: I am not interested in talking for the sake of talking," the president said. "But I do believe that we can move US-Cuban relations in a new direction."
Earlier Hillary Clinton, also welcomed Castro's comments. "We welcome his comments, the overture they represent, and we are taking a very serious look at how we intend to respond," she said.
In another sign of changing times, the OAS Secretary-General said he would ask the 34 member nations to invite Cuba back into the fold.