To be sure, there is still far more that separates the long-time antagonists than unites them.
The State Department has kept Cuba on a list of state sponsors of terrorism and another that calls into question Havana's commitment to fighting human trafficking. The Obama administration continues to demand democratic change on an island ruled for more than a half century by Castro and his brother Fidel.
For its part, Cuba continues to denounce Washington's 51-year-old economic embargo.
And then there is Gross, the 64-year-old Maryland native who was arrested in 2009 and is serving a 15-year jail sentence for bringing communications equipment to the island illegally. His case has scuttled efforts at engagement in the past, and could do so again, U.S. officials say privately. Cuba has indicated it wants to trade Gross for four Cuban agents serving long jail terms in the United States, something Washington has said it won't consider.
Ted Henken, a professor of Latin American studies at Baruch College in New York who helped organize a recent U.S. tour by Cuban dissident blogger Yoani Sanchez, said the Obama administration is too concerned with upsetting Cuban-American politicians and has missed opportunities to engage with Cuba at a crucial time in its history.
"I think that a lot more would have to happen for this to amount to momentum leading to any kind of major diplomatic breakthrough," he said. "Obama should be bolder and more audacious."
Even these limited moves have sparked fierce criticism by those long opposed to engagement. Cuban-American congressman Mario Diaz Balart, a Florida Republican, called the recent overtures "disturbing."
"Rather than attempting to legitimize the Cuban people's oppressors, the administration should demand that the regime stop harboring fugitives from U.S. justice, release all political prisoners and American humanitarian aid worker Alan Gross, end the brutal, escalating repression against the Cuban people, and respect basic human rights," he said.