This is certainly not the FIRST cat race to Cuba. It happened at least twice in the late 90's, and maybe early 2000's, organized by (I think the name is) George Ballenger, of Key West. I don't know if he is still there and still doing it, but I know he got stopped at some point by the Treasury Department.

We had a story and picture about one of his trips (I think all on Hobie 16's) in "Catamaran Sailor."

After they got to Veradero, they hooked up with Hobie sailors in Cuba and had a race over to Havana and then had buoys races there with the Cubans.