Critics of the island's communist-run government complain officials want to keep technology -- and the open flow of information-- out of their citizens' hands.
The Cuban government has long blamed the U.S. trade embargo for the scarcity of Internet.
But in July, Cuba for the first time opened 35 areas with public Wi-Fi across the island.
University student Alexi sat crouched on the sidewalk at one of the new areas instant messaging with his mother, who he said lives in Italy.
The $2-an-hour charge to use the Internet was less expensive than calling her, he said, but still too high for a country where the median salary is about $20 a month.
"It's not super reasonable, but it's a start. Hopefully the price will keep going down," Alexi said. "One day it would wonderful to have Internet in my house, then I wouldn't have to come out here," he said gesturing to his fellow web surfers camped out on the pavement.
Cuba has among the lowest levels of connectivity in the world. The government is the only authorized provider, there's no mobile Internet. Home access is close to unheard of.
Cuban filmmaker Yaima Pardo criticized the lack of Internet in her documentary "Off_Line."
Although her film is available on the Internet, Pardo said because of the lack of connectivity, she had to distribute the documentary in Cuba on thumb drives.
"It disconnects us from the 21st century, we are being held back, we don't have the same rights that the rest of the world has," Pardo said.
Some Cuban exile groups have tried to skirt restrictions and smuggle in technology.
"We regularly send computers, laptops, flash drives, DVDs and we do cell phone recharges for people on the island," said Jose Luis Martinez of the "Connect Cuba" campaign, which promotes more Internet access on the island.
"The Cuban government is very tight with what technologies they allow into the island so we don't [get] things in bulk," Martinez said. "It's really one or two at time and hope they don't get confiscated."
Suspicions of outsiders remain
The Cuban government has long been suspicious of outside groups trying to improve connectivity on the island.
U.S. State Department contractor Alan Gross spent five years in Cuban jail for importing banned satellite communications equipment. He was freed in 2015 as part of a deal that led to the re-establishment of diplomatic relations with Cuba and the United States.
Recently officials from Google offered to improve Cuba's Internet infrastructure, free of charge.
"Everyone knows why Cuba doesn't have more Internet, it's too expensive," said Cuban Vice President Jose Ramón Machado Ventura in a July interview with the island's state-run media. "Some want to give us it for free so the Cuban people can communicate, but their real purpose is to infiltrate us ... to destroy the revolution."
The message from Cuban officials appears to be that they will get the island online but at the pace they choose.