Cuba was once the crown jewel of the Caribbean – until communists stole it 65 years ago.
Now Trump is strangling the regime into submission, and DeSantis just laid out what comes next.
And what DeSantis said your grandkids will be doing there is something Democrats spent decades making sure you'd never see.
DeSantis Paints the Picture of a Free Cuba
Speaking at West Palm Beach's DeSantis Family Chapel, Florida's governor sketched a picture of the island that Americans haven't been able to touch since Kennedy was president.
"Some of your kids and grandkids will be going to Spring Break there," DeSantis said. "They'll be going on honeymoons there. People will be doing golf trips there."
He believes a "pro-Western, pro-America, free government in Cuba would be a boon for that island."
And he made clear exactly who should rebuild it – not Cubans flooding into Florida.
"People in Cuba and people in the US, maybe exiles, who want to be a part of a solution" should be "in Cuba doing that," DeSantis said.
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This isn't nostalgia. It's a roadmap.
The Island America Lost
Before Castro, Cuba wasn't just a tourist spot – it was the American playground of the Western Hemisphere.
More than 350,000 Americans made the trip in 1957 alone – a $50 flight from Miami got you round-trip airfare, a hotel room, meals, and entertainment.
Frank Sinatra, Ava Gardner, and Ernest Hemingway called Havana a second home.
"Havana was then what Las Vegas has become," University of North Carolina Cuba historian Louis Perez told the Smithsonian. By 1961 – just two years after Castro – that 350,000 had collapsed to 4,000.
Sixty-five years of communism took the most perfect tourist destination in the Western Hemisphere and destroyed it.
DeSantis isn't describing something new.
He's describing something stolen.
Trump Is Already Making It Happen
This isn't a campaign speech. The pressure campaign is real and it's working.
On January 29, 2026, Trump signed an executive order declaring Cuba's government "an unusual and extraordinary threat" to U.S. national security – and imposed tariffs on any country supplying Cuba with oil.
After the U.S. military removed Maduro from Venezuela in January, Trump cut off the Venezuelan oil that had been Cuba's economic lifeline for two decades.
The White House has been direct: the Cuban regime hosts Russia's largest overseas signals intelligence facility, provides safe haven for Hezbollah and Hamas, and persecutes political opponents while the country collapses.
Cuba's GDP is projected to contract 7.2% in 2026, following a 5% decline in 2025 – a total economic collapse of 23% since 2019.
Havana's garbage is piling up in the streets because the city's trucks have run dry – barely 40 percent of the fleet can still operate.
"What's happening with Cuba is amazing," Trump said earlier this month. "We want to finish this one [Iran] first."
The Bigger Picture DeSantis Sees
DeSantis was measured on Venezuela – and that measured skepticism tells you everything about how seriously he takes actually finishing the job.
"Getting Maduro was an amazing operation," he said – but he noted that Venezuela's remaining regime figures are still in place, with only the threat of the same fate keeping them in line.
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He's right. A free Cuba doesn't happen because a dictator falls.
It happens because what replaces him actually respects the rule of law.
That's why DeSantis isn't promising a flood of Cuban migrants into Florida.
He wants them staying home – rebuilding.
The communist regime spent six decades turning one of the most naturally perfect tourist destinations in the Western Hemisphere into a blackout-ridden garbage pile where doctors beg for Tylenol.
What Trump and Rubio are doing right now – the oil blockade, the economic siege – is the predicate for everything DeSantis just described.
Your grandkids booking their honeymoon in Havana isn't a fantasy.
It's the endgame.
Sources:
- "Fact Sheet: President Donald J. Trump Addresses Threats to the United States by the Government of Cuba," The White House, January 29, 2026.
- A.G. Gancarski, "Spring Break, honeymoons, golf trips: Ron DeSantis believes free Cuba could be American playground," Florida Politics, March 26, 2026.
- "U.S. Policy Toward Cuba: Recent Developments and Congressional Considerations," Congressional Research Service, Congress.gov, 2026.
- "2026 Cuban Crisis," Wikipedia, updated March 2026.
- "Cuba's Tourism Could Boom if Trump Liberates Its People Like Venezuela," World Property Journal, 2026.
- "Before the Revolution," Smithsonian Magazine, November 2013.
