It was only 10 years ago that Cuba opened up to cruise ships. From about 2016 to 2019, at least four major cruise lines started taking passengers to the tropical island, which was the hottest destination at the time. Now, there is legal trouble for the cruise lines that sailed to the port.

I was lucky enough to sail to Cuba during this time period, taking a Royal Caribbean ship to the Havana port. I shared my thoughts on Majesty of the Seas during only her third-ever voyage to the island and put together a slideshow video of what it was like in Cuba at the time.
It was incredible to watch the ship pull past Morro Castle into a port that felt frozen in time.
But while passengers were busy enjoying taking limited shore excursions through Old Havana, a legal time bomb was quietly ticking in the background.
Now, the U.S. Supreme Court has weighed in, and it means four major cruise lines are officially back on the hook for a $440 million penalty.
What is This Lawsuit All About?
To understand how we got here, we have to look back long before modern cruise ships ever docked in Havana. Way back in 1960, shortly after Fidel Castro took power, the Cuban government confiscated millions of dollars’ worth of private property from Americans without paying them for it.
One of those seized assets was the main port terminal in Havana. A U.S.-based company called Havana Docks held the original contract to operate that exact pier.
Then, in 1996, the U.S. passed the Helms-Burton Act. A specific clause in that law allows Americans whose property was stolen by the Cuban government to sue any commercial company that later steps in and makes money off that stolen property.
For over 20 years, U.S. presidents blocked those lawsuits from actually happening to avoid major international legal messes. But in May 2019, the administration officially allowed the law to take effect.
Havana Docks immediately sued Carnival Cruise Line, Royal Caribbean, Norwegian Cruise Line, and MSC Cruises for using their port.
The “Lease Expiration” Battle
The cruise lines fought back. Their main legal defense was all based on a specific timeline. Havana Docks’ original contract was set to expire in the year 2004.
Because the cruise lines didn’t start using the port until 2016, they argued that Havana Docks wouldn’t have owned the rights to the port by then anyway, so no damages should be owed.
At first, a lower appeals court actually agreed with the cruise lines and threw the fines out.
But the Supreme Court just declined to take up the cruise lines’ appeal, effectively reversing that decision.
The ruling states that if a company profits from property that was wrongfully taken, the original claim remains valid, even if a lease would have timed out.
What Does This Mean for the Cruise Lines?
The original judgment ordered the four cruise lines to pay a combined $439 million in damages, interest, and attorney fees. With the Supreme Court passing on the case, that huge payout is now back on the table.
It is important to note that the cruise lines weren’t intentionally breaking the rules at the time.
Between 2016 and 2019, the U.S. government actively encouraged educational and cultural “people-to-people” travel to Cuba, and the lines were operating under strict federal guidelines.
This educational travel experience was the reason I was not allowed to just roam around Cuba and had to be very specific in my reasons for being there.
Will Cruise Ships Ever Go Back to Cuba?
For cruisers holding out hope that Havana will return to short Caribbean itineraries anytime soon, this ruling could set that back a bit.
By confirming that using the port counts as “trafficking in stolen property,” the Supreme Court has made the Havana docks a troublesome area that they may not want to test until there is more clarity.
Even if political relations between the U.S. and Cuba get better, cruise lines won’t be able to touch the port before resolving these claims first.
For now, that little window of Cuba cruises from 2016–2019 look like a blip on the radar of cruise history that many of us hope opens again someday.
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