Florida Keys

Coast Guard makes arrest after stopping a sailboat heading from the Keys to Cuba

Federal agents arrested a British man who the Coast Guard found on a sailboat heading from the Florida Keys to Cuba on Wednesday, Aug. 20, 2025. Court records show he had twice been ordered by a judge to leave the United States.
Federal agents arrested a British man who the Coast Guard found on a sailboat heading from the Florida Keys to Cuba on Wednesday, Aug. 20, 2025. Court records show he had twice been ordered by a judge to leave the United States. Miami Herald File

The crew of the U.S. Coast Guard Cutter Maple last Wednesday morning stopped a sailboat about 40 nautical miles south of the Middle Florida Keys city of Marathon that was heading for Cuba.

On board were three people of varying backgrounds, including a British man with a history of using aliases, getting into trouble with the law and who’s been deported several times, according federal court documents.

The 43-foot Stormy Weather had a woman and two men on board, and the vessel did not have authorization to enter Cuba nor Cuban territorial waters, agents with Homeland Security Investigations said in a criminal complaint.

One of the men on board, 41-year old Miles Connors, is a citizen who has been ordered removed from the U.S. twice since 2008 after several interactions with immigration officials at airports and other points of entries throughout the country going back to 2006, his complaint states.

In February 2008, U.S. Customs officials in Massena, New York, a point of entry on the Canadian border, deemed him inadmissable to the country, and a judge ordered him removed.

Two years later, he was stopped by police and arrested on a charge of driving without a license. He was flown out of the country back to the United Kingdom in June 2010, according to the complaint.

When he was deported, the name on his passport was Myle O’Connor, and agents say he was found to have has used different variations of that name each time he came in contact with immigration officials. The name on his current passport is Miles Anthony Connors, according to the complaint.

The complaint also says Connors has an outstanding arrest warrant in Pennsylvania issued in January. It did not state what charge he’s facing there, but Pennsylvania court records show that a Miles Anthony O’Connor was arrested on a charge of operating a vehicle without a valid inspection in June in York County.

The captain of the Stormy Weather is a Russian-born U.S. citizen, who agents did not name in the complaint. The woman on the boat is the vessel’s registered owner, who agents say is a Canadian citizen who entered the U.S. on a valid B2 non-immigration visa in July.

Agents determined that the trio left on the boat from Poncho’s Fuel Dock and Supplies near Boot Key Harbor in Marathon around 10:30 a.m. Tuesday, Aug. 19. They got that information after interviewing the boat owner and captain and from watching security camera footage from the marina, according to the complaint.

Agents did not indicate in the complaint if the two people said in the interview why they wanted to go to Cuba.

Federal prosecutors have filed a motion to have Connors held until his trial on one count of re-entry of a removed illegal alien. His next court appearance is scheduled for Sept. 5.

It wasn’t immediately clear where Connors was being held. He’s being represented by a federal public defender, who did not immediately respond to a request for comment from the Herald.

David Goodhue
Miami Herald
David Goodhue covers the Florida Keys and South Florida for FLKeysNews.com and the Miami Herald. Before joining the Herald, he covered Congress, the Environmental Protection Agency and the Department of Energy in Washington, D.C. He is a graduate of the University of Delaware. 
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