An American adventurer who set sail from North Carolina to New Zealand about 18 months ago has ended up imprisoned in Russia, sentenced to five years after being convicted of “arms smuggling” because of a rifle, a pistol and ammunition that he kept aboard his sailboat.
Charles Wayne Zimmerman had headed toward Russia in hopes of meeting a young woman he had encountered on Instagram who went by the handle Evil Elya, having complimented her on her looks and twice sent her flowers, according to a sentencing document posted on Friday by the Central District Court in the Black Sea resort town of Sochi.
Mr. Zimmerman, 58, appears to be the latest American who the Russian authorities have grabbed in pursuit of what is called “hostage diplomacy,” meting out harsh sentences to U.S. citizens in order to trade them for Russians held abroad or other diplomatic gains.
A spokesman for the U.S. State Department confirmed Mr. Zimmerman’s incarceration and said it was providing “consular assistance” for him, without further details. No U.S. diplomat has visited Mr. Zimmerman, who goes by Chuck, since he was first detained last June, his younger sister, Robin Stultz, said in brief remarks via email on Friday.
Ms. Stultz, a bank manager in Virginia, had earlier issued a statement, saying, “This is an obvious set up to get another American they can trade.” How Mr. Zimmerman came to be in Russia remains somewhat murky, as the version of events presented by his family and that in the court documents differ. Ms. Stultz maintains that the Russian Navy forced her brother to sail to Sochi after intercepting his sailboat almost immediately after he entered the Black Sea.
Steve Witkoff, the presidential envoy who has been negotiating with the Kremlin on a peace deal in the Ukraine war, was believed to have raised the issue of Mr. Zimmerman and other incarcerated Americans during his repeated visits to Moscow, according to Kieran Ramsey, the chief investigative officer of Global Reach, an organization in Washington that helps families seeking the release of Americans imprisoned abroad.
Mr. Witkoff, who was most recently in Moscow on Thursday, could not immediately be reached for comment. At least 10 Americans are jailed in Russia.
Although Mr. Zimmerman was arrested in Sochi in June 2025, the case came to light only after a Russian appeals court issued a statement on Monday confirming that it had upheld the five-year sentence announced in October. The statement included a video of Mr. Zimmerman sitting on his sailboat, along with glimpses of a rifle and ammunition boxes.
One witness, who had participated in the inspection of the sailboat, said that she had spotted a rusty pistol on a table, and Mr. Zimmerman then volunteered that he had another weapon, digging out the rifle, court documents said. He kept it onboard for protection, according to his sister.
“Of course he had a firearm on board,” Ms. Stultz said in her statement. “You can’t just call 911 if something goes wrong out at sea.”
In appealing the sentence, Dmitry Starkov, Mr. Zimmerman’s lawyer, said that Mr. Zimmerman had been unaware that having the weapon was illegal under Russian law. He argued that a five-year sentence was excessively harsh, according to documents from the appeals court. Reached by telephone, Mr. Starkov declined to comment further.
Mr. Zimmerman, a U.S. Navy veteran and a master electrician, had used his life savings to buy the 35-foot sailboat to fulfill his dream of sailing around the world, according to a website his family made to help seek his return. The father of two daughters, he had lived most of his life in Salem, Va., but had arranged to work in New Zealand.
Ms. Stultz said that she had been in touch with her brother by text message almost daily before his detention. “He’s my rock,” she said. Before Russia, he had stopped in Portugal, Spain, Sicily, Greece and Turkey, court documents said.
His family said that they were not aware of plans to visit Russia, nor of any contact with a woman there. But Mr. Zimmerman had obtained a Russian visa, court documents indicated.
The Russian Navy intercepted the sailboat in international waters on June 17, and then escorted it on a 22-hour trip to Sochi, according to the family website. Russian court documents do not mention any interception.
The woman on Instagram told the court that she did not know Mr. Zimmerman. She had written him only once — back in 2022 to thank him for the first batch of flowers — and then blocked him when he persisted, according to court documents. She worked for the Russian tax service, the documents said.
The woman, whose full name was redacted, lived in Kazan, deep in the interior of Russia and about 1,200 miles northeast of Sochi.
Mr. Zimmerman is being held in a Russian penal colony in the Krasnodar region. The seven months he has already spent imprisoned in Russia will count toward his sentence, court documents said.
Alina Lobzina contributed reporting.
Neil MacFarquhar has been a Times reporter since 1995, writing about a range of topics from war to politics to the arts, both internationally and in the United States.
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