I met someone in Nyack NY who had done the race, and met Fidel at the supper afterwards. The story was fascinating, but I can't recall it well enough to tell it here. Sarasota Yacht Club has tried for several years to restart the race, the OFAC simply wouldn't ok it, no matter how hard they tried and how many hoops they jumped through.
The course would be Sarasota - Key West, Havana. You run not quite at right angles to the current then, and since the winds are usually out of the east with an east setting current, it can get lively. Mind you, I've seen it completely flat on one crossing. Very odd that was.
Calder recommends crossing after a norther and riding in on the NW winds. The trick there is not to get to Hemingway's entrance channel before the waves subside - it can be VERY difficult if the conditions are rough. For those who want to see what a fairly mild day looks like, go to SAIL, Cruising Cuba: Paso Malo | Sail Magazine
, and take a look at my video of Varadero's Paso Malo (Bad Pass). It's not much different from the Hemingway entrance - a washing machine or worse given the right conditions.