One man’s inspiring love story is another’s dark comedy. Enter North Carolina man Charles Wayne Zimmerman, who, in his late fifties, fell in love with a Russian woman he’d met online. Truly, a tale as old as time.
But rather than take the traditional course of sending her increasingly large amounts of money as she comes up with repeated excuses as to why they can’t meet in person, Zimmerman decided to take to the high seas!
He clambered aboard his yacht, the Trude Zena, and embarked on what would end up being an 11-month trip across the world from Fort Macon NC, all the way to the Black Sea port of Sochi. En route, he stopped in Portugal, Spain, Italy, Greece, and Turkey. Finally, in June 2025, he docked in Sochi, albeit illegally and without a visa.
Absolutely crazy story here: A US citizen sailed his own yacht from America to Russia to meet a girl from Kazan he'd chatting with online. The journey took almost a year (with stops in Portugal, Spain, Italy, Greece and Turkey).
— Brian McDonald (@27khv) January 19, 2026
When he finally docked in Sochi, illegally and… pic.twitter.com/TT2KCTAkV0
But he had love in his heart, so naturally the Russian authorities smiled, patted him on the head, and sent him on his way. Or, uh, maybe not. The incredibly suspicious Russian customs agent promptly searched Zimmerman’s boat and found a rifle and ammunition, which he’d apparently packed for self-defense.
As it turns out, arriving uninvited at a Russian port with a rifle and ammunition isn’t a great idea, and Zimmerman was arrested on the spot, and his yacht seized. Now, as reported by the Moscow Times, his trial is complete, and he’s been sentenced to five years in an undetermined penal colony.
I’m sure she’ll wait for him to be released…
The Courts of the Krasnodar Territory put out a press release that says Zimmerman explained to the court that:
He met a girl online who lives in Kazan and decided to join her in Russia on his yacht. Before setting out, he didn’t bother to research Russian laws and assumed that the weapons he kept on board for self-defense should simply remain on board at all times.
They underline that “ignorance of the law does not exempt from liability” and confirm that:
“The Central District Court of Sochi found a US citizen guilty of illegally transporting and moving firearms, the main part of a firearm (barrel), and ammunition across the customs border of the Eurasian Economic Union. The court sentenced him to five years’ imprisonment in a general regime penal colony.”
It’s hard not to feel some sympathy for this lovelorn sailor who braved the open ocean for a chance to see his Russian lady-love in person, and five years in what’s presumably not a particularly pleasant penal colony seems unduly harsh.
The reaction of his anonymous Russian crush remains a mystery. Here’s hoping she can at least visit him in the penal colony, so he’s got something to keep him going between the backbreaking hours of forced labor.
