Following the Cuban revolution, the monument was stripped of the eagle that once sat at the top and busts of the sailors were removed.
But as new rules allow Cubans to own private businesses, a revitalization is under way along the Malecon, and a renewed relationship is forming with the US. Last week President Barack Obama said he wants Cuba removed from the list of states sponsoring terrorism and this week Governor Andrew Cuomo led a trade mission in Havana.
"This is not about starting a friendship. We had a friendship that went on for decades. It is about rekindling a friendship," said Cuomo.
Boris Cabrera sells Cuban souvenirs at a market just off the Malecon.
Half of his family lives in the United States.
But Cabrera can't visit them because of the embargo between U.S. and Cuba.
"It's the human right," said Cabrera. "I'd be very happy if I can go to the United States and come back."
Which is why he and so many Cubans are optimistic about a renewed relationship.
"Everybody here is very happy with Obama."
But removing the embargo still faces some big human-rights hurdles.
And some Cubans say a renewed relationship doesn't mean the U.S. can dictate Cuban policy.
"Everything is going to be based on respect," said Christopher Elias. "We don't have to tell you what you have to do in your country, so you don't have to, you cannot tell us what we have to do in our country. That's the base, respect."
Finding a balance between capitalism and communism won't be easy either.
But Elias says he's confident Cubans will still receive public assistance in a free market.
"The government has been taking care of us since the very beginning. I think they're going to still do it."
Jose Buscaglia is a professor at SUNY Buffalo who has traveled to Cuba for almost 20 years.
Buscaglia says when he first arrived there was a lot of scarcity and Havana was completely dark at night.
While there are some hopeful signs, he says there is still a long way to go.
"Things have gotten much better, although I think that the level of the daily life of Cubans, they still toil quite a bit to make ends meet and put food on the table every afternoon," said Buscaglia.