KEY WEST, Fla. — At the end of the Florida Keys island chain, Key West is closer to Havana than Miami. Tourists line up for a picture with the “90 miles to Cuba” concrete buoy on a seawall to prove it.
U.S.-Cuba conflicts are not new for the country’s southern-most city. The laid-back island made of coral rock was the 1962 Cuban Missile Crisis front-line military outpost.
Barbed wire lined the beaches. The U.S. Army took over the 1920 Casa Marina hotel. President John F. Kennedy was in Key West to inspect the HAWK anti-aircraft missile sites.
“The federal government actually armed local law enforcement with heavy military weapons,” said Monroe County Sheriff Rick Ramsay, who has more than three decades in law enforcement.
Some tourists in Key West said they were concerned. U.S. President Donald Trump stands firm on his new policy with Cuba. U.S. Secretary of State Marco Rubio referred to the communist island as a national security threat. Raúl Castro is a wanted man.
The U.S. Southern Command welcomed aircraft carrier USS Nimitz, the embarked Carrier Air Wing 17, USS Gridley, and USNS Patuxent on Wednesday to the Caribbean.
The U.S. Naval Air Station Key West on Boca Chica Key is just about four miles east of the central business district of Key West.
“Our installations remain vigilant and will take appropriate actions to ensure the safety and security of our U.S. service members, civilians, contractors, and their families,“ a spokesperson for the U.S. Navy Southeast said in a statement on Thursday.
Ramsay said he too was vigilant. He urged calm on Sunday after Axios reported that Cuba had acquired more than 300 military drones and Cuban officials were discussing plans to hit U.S. targets.
U.S. Rep. Carlos Giménez warned Cuba had suicide drones from Iran. CIA Director John Ratcliffe met with Cuban officials on May 14 in Havana and delivered a warning.
The U.S. Navy reported there was an exercise with “unmanned systems and artificial intelligence” in late April in Key West. Earlier this month, SOUTHCOM shared images of exercises in Key West with “semi-autonomous” drones.
Autonomous and unmanned forces:@NAVSOUS4THFLT's #FLEX2026 exercise in Key West, Florida, last week advanced SOUTHCOM objectives to leverage cutting-edge technology to support the National Defense Strategy.
— U.S. Southern Command (@Southcom) May 8, 2026
The exercise formed the foundation of the newly established SOUTHCOM… pic.twitter.com/30q8i7I0eb
Next-generation capabilities:@NAVSOUS4THFLT's #FLEX2026 exercise in Key West, Florida, is advancing SOUTHCOM objectives to embrace autonomous, semi-autonomous, and unmanned platforms and systems to counter threats and challenges in the region.
— U.S. Southern Command (@Southcom) April 28, 2026
These successes are forming the… pic.twitter.com/gNp4TyAqMP
Ramsay said he hasn’t seen or received reports of any recent activity in Monroe County that concerns him, but he knows what to look for.
“We would probably see an increase in jets at Naval Air Station Key West,” Ramsay said. “We have seen no increase in ground, air, or sea assets.”
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