Cuomo landed in Havana Monday for the two-day trip with a host of elected officials and business leaders, including Assembly Speaker Carl Heastie, Senate Minority Leader Andrea Stewart-Cousins and Independent Democratic Conference Leader Jeff Klein.
Yogurt maker Chobani, airline Jet Blue and MasterCard are a few of the businesses taking the trip with Cuomo.
"We've become much more aggressive in going out and seeking business opportunities for New York, what we call Global NY which is where we look for international business opportunities for the state of New York," Cuomo at the start of a business roundtable in Havana, according to a video recording of the meeting.
The trip is the first in Cuomo's $35 million Global NY initiative.
Although Cuomo says the trip is to develop business relationships, he has faced pressure to speak about the lack of gay rights Cuban residents face.
Cuomo helped push through New York state's Marriage Equality Act. Earlier this month, he banned non-essential travel to Indiana after a religious freedom law there was criticized for allowing discrimination against the LGBT community.
"Isolation has not worked. We've had 50 years of isolation and it has not worked," Cuomo said. "Engagement and full relationships is the best way to have a dialogue on the issues we agree with and on the issues that we disagree about," the governor added.
Not everyone believes the trip is worthwhile.
John Kavulich, president of the U.S.-Cuba Trade and Economic Council, said Cuomo's trip is taking place too early.
"It's a visit that should take place, it just shouldn't take place now," he said.
Official diplomatic relations with Cuba have yet to be restored, meaning that no trade agreements can be negotiated.
"When Cuba gets diplomatic relations established, Cuomo has more leverage to say: 'How can I help companies in my state export products to Cuba?'" said Kavulich. "Far more important than being the first governor to visit Cuba after Obama's announcement would have been for him to be the first governor walking into the new United States Embassy in Cuba."
Cuomo, acknowledged that diplomatic relations had not been restored.
"Longer term, we are looking forward to the embargo, as we call it in the United States, being lifted legally by Congress so that we can have a normalization of relations," said Cuomo.
Cuomo, not known for his international travel, will keep the trip brief at less than 48 hours.
"After this last election a lot of people said Cuomo has no shot to run for president," said Falcón. "This trip rings speculation about his aspirations for national office and efforts to try to boost his profile."
But if Cuomo is looking for a boost from the Latino community from this trip, he may have miscalculated.
"The main buzz in the Latino community is about the lack of Latinos on the trip," said Falcón.
Jose F. Buscaglia-Salgado, director of Caribbean, Latin American, and Latino Studies for the University at Buffalo, is the only Latino official identified by the governor's office as attending the trip.
None of the legislators are Latino and none of the businesses appear to be Latino-owned.
"It's ridiculous to go to Cuba and not be able to identify any Latino businesses to take on the trip or identify any Latino legislators to go on the trip," said Falcón.
"This is taxpayers shelling out a lot of money for a trip whose purpose is not clear it, which seems more political than economic and that raises more questions than answers," he added.
The governor's office did not provide the cost of the trip.
Cuomo's itinerary Monday includes a meeting with Rodrigo Malmierca Díaz, the Cuban Minister of Trade and Foreign Investments, First Vice President Miguel Diaz-Canel and Cardinal Jaime Lucas Ortega y Alamino.
During the roundtable meeting the governor praised Cuban President Raúl Castro and President Barack Obama and joked about receiving his first Cuban cigar from Diaz "which I intend to enjoy right after this meeting," Cuomo said.
After the meeting, Cuomo took a walking tour of Old Havana where he checked out an antique car and met with students from the State University of New York who are studying in Cuba as a part of exchange programs.
"We believe this is going to be a dramatic change that is going to be to the benefit of the people of Cuba and also to the people of the United States," said Cuomo.