Florida Man Hijacks Key West Tour Train for Drug-Fueled Birthday Joyride

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Florida Man Hijacks Key West Tour Train for Drug-Fueled Birthday Joyride

KEY WEST, FL — A Florida man’s birthday celebration turned criminal when he stole a trackless tourist train, picked up passengers, and took it for a spin through downtown Key West — while reportedly high on meth.

Authorities say Jonathan Patrick Winslow, who turned 57 on the Fourth of July, was arrested after duping an employee at the Conch Tour Train Depot into handing over the keys.

“It’s My Birthday,” Said the Imposter Conductor

According to the arrest report, Winslow showed up at the depot claiming he used to work there and asked for a tour of the train. Believing the story, an employee gave him access — only to watch Winslow drive away with the vehicle moments later.

He did not have permission, police later confirmed.

While officers were quickly dispatched, they already had a key clue — Winslow had left his Kia running in the parking lot with rock music blaring, making it easy to track him down.

Police Stop “Joyride” Through Downtown

The sightseeing train was located via GPS and found intact — but not empty. Winslow had somehow convinced two tourists to hop on board, thinking they were getting a legitimate tour.

Police noted Winslow was behaving erratically with “rapid speech” and extreme excitement, even while being informed of the charges. He continued to claim he only “borrowed” the train and reiterated it was his birthday.

Meth Pipe Found at Jail

During a search at the county jail, officers reportedly discovered a pipe hidden in Winslow’s pocket. While he insisted it was for marijuana, officials identified it as a methamphetamine pipe.

He now faces multiple charges, including:

  • Burglary
  • Grand theft auto
  • Possession of drug paraphernalia

Read Also: Retired Teacher Sets Sail on 15-Year Cruise, Says It’s Cheaper Than Living in California

Not the First Joyride

This strange theft mirrors an incident earlier this year in New York City, where a group of teenagers stole and drove an empty subway train, even posting their escapade on Instagram. Two were arrested and charged in February.

Should Security Be Tightened on Public Vehicles?

From Florida’s tourist trains to NYC’s subway cars, these incidents raise serious safety questions.
What do you think? Should these attractions have stricter safeguards or better staff training?

Share your thoughts in the comments or join the conversation at ridgecrestpact.org.

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Doris Oliver

Doris Oliver is a proud Ridgecrest native with a deep passion for bringing local stories to light. With over 2 years of experience in community reporting, Doris has built a trusted voice in the Community. Her work focuses on covering the issues that matter most to Ridgecrest residents — from public safety and education to local government and community events. Driven by a belief that informed citizens make stronger communities, Doris is committed to delivering accurate, timely, and impactful news. Through ridgecrestpact.org, she aims to bridge the gap between people and the stories shaping their everyday lives — making local news accessible, engaging, and meaningful.

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