Florida Man Steals Key West Sightseeing Train on Meth-Fueled Joyride on His Birthday — Picks Up Passengers

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A Florida man celebrated his birthday in the wildest way imaginable — by stealing a Conch Tour Train in Key West, taking it for a joyride through downtown, and even picking up unsuspecting passengers along the way, all while allegedly high on meth.

The incident occurred on July 4, which also happened to be Jonathan Patrick Winslow’s 57th birthday. According to Key West police, Winslow showed up at the Conch Tour Train Depot on Staples Avenue and convinced an employee to give him access to the train by claiming he had previously worked for the company and wanted a quick tour.

The employee, thinking the request might be legitimate, was left stunned as Winslow drove off in one of the iconic sightseeing trains — a trackless trolley that’s a familiar sight for tourists in the Florida Keys.

When police responded to the depot, they found Winslow’s Kia still running in the parking lot — with rock music blaring from the speakers, according to the arrest report.

Thanks to GPS tracking, officers quickly located the stolen Conch Train downtown, near Duval and United streets, where another employee was able to safely retrieve the vehicle.

Local10/MCSO

Authorities said Winslow had picked up two random passengers during his unauthorized excursion.

Police eventually found Winslow at the Southernmost Point Buoy, where he was reportedly talkative and hyperactive, displaying rapid speech and visible excitement. When informed that he was being arrested, Winslow insisted he was just “borrowing” the train — and reminded officers, “Today is my birthday.”

He was taken to the Monroe County Sheriff’s Office jail facility, where a corrections deputy discovered a pipe in his pocket. Winslow claimed it was a weed pipe, but authorities later confirmed it was a methamphetamine pipe.

Winslow now faces three criminal charges:

  • Burglary
  • Grand theft auto
  • Possession of drug paraphernalia

He was booked into jail with a bond set at $60,000.

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