John Young, of Key West, Fla., has organized sailing trips to Cuba for more than a decade. He’s been licensed to do so by the federal government because of the food and medicine the boats carried to the island. U.S. policy has allowed travel to Cuba for humanitarian purposes.

But a federal grand jury now is apparently deciding whether Young’s last trip, in May, warrants criminal charges — an exceedingly rare tool in the U.S. government’s enforcement of the Cuba travel ban.

“We try as much as we can to avoid the politics of this,” Young said. “It doesn’t do us any good, though.”

Young is the founder of Conchord Cayo Hueso Inc., a nonprofit organization that has made aid trips to Cuba since 1992. The group, Young admitted, also has a little fun along the way.

The May trip, for example, doubled as a race, with the fastest of the roughly 20 boats that made the trip vying for the “Conch Republic Cup.”

Young said only half the vessels in the regatta had licenses to carry humanitarian goods to Cuba. But the unlicensed vessels, he said, shared the burden.

Each boat carried a little more than 20 pounds of medical supplies, including antibiotics, anti-inflammatories and pain relievers.

“These are desperate people down there. These medicines help an urgent situation,” Young said. “We’re very proud of what we do. We sleep better than most people do at night.”

The U.S. Attorney’s Office for the Southern District of Florida declined comment.

Criminal sanctions have been used little, if ever, in the cases of Cuba violators. Prosecutors across the federal government could not recall any such cases; the federal government’s Bureau of Justice Statistics said three criminal cases were brought under the Trading with the Enemy Act in 2002, but couldn’t say if the cases involved Cuba or not.

These are not frequent statutes charged,” said Mark Motivans, a statistician with the bureau.

The grand jury investigation is a “shocking departure” from previous practices, said Art Heitzer of the National Lawyers Guild Cuba committee, which opposes the travel ban.

Young said he was frustrated waiting for the federal government to act. His license to carry humanitarian aid was revoked after the May regatta. He doesn’t know what’s happening in the grand jury — he can only surmise based on the comments of other sailors who have been called to testify.

“It’s very, very strange,” Young said, “for a democracy.”

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