Guys,
I have sailed to Cuba three times, the last time in my E-27. As chance would have it, I talked with a skipper just today who has signed up for this race. If memory serves, he said there were 13 entries so far. The entry fee is $1K. That's a bit limiting. The reason for the race is that it's a feeder for a subsequent 15-mile race along the waterfront from Marina Hemingway to the entrance to Habana Harbor and back.
When I went down in 2004, I had to have permission from the Office of Foreign Assets Control (OFAC), a Treasury Department division that's good at saying "no." On top of that, I was required by law to register with the United States Coast Guard Marine Intelligence Division (Miami) because I was exiting a Defense Identification Zone. I was required to get an export license for my boat from the Department of Commerce. The OFAC "okay" was pretty much routine. I had paperwork from the head of OFAC saying that if I was a journalist, and I be one of those, I was free to go. Cigars and rum were proscribed by W well after we got back, but I brought back rum. The Coast Guard broke one of the bottles when a cutter put out a large wake in Key West Harbor. I filed a claim for $10 against the Coast Guard for the rum. They hemmed and hawed for two years, but they paid. I don't smoke. Besides, cigars that were $35 a box when I had last been down there in 1999 were, in 2004, $135 a box. Romeo & Juliettas. My advice to the wannabes is don't mess with the regs. The government can be very nasty, it it so chooses. At this juncture, no blanket permission has been granted and no specific permission has been granted. You can go to Cuba legally, but you cannot spend one nickel down there legally. Not now.
If you do go, don't buy anything off street kids. It's universally counterfeit. Particularly cigars. The Floradita Lounge, where Hemingway hung out, is great, but a couple of doors down the street drinks are just as good and half the price. The music at Monserrat (same area) was to die for. Crystal beer is the best. To skip having a drink at the Hotel Nacionale is to miss hanging out where Gary Cooper, Myer Lansky and others whose names I have forgotten liked to relax. There is First Class in Habana and then there are the rest of the places. The first night there I had a mojito in Marina Hemingway. The mint had been chewed on by weevils. After that it was Crystal. Except at the Hotel Nacionale. See Habana Viejo. See the Museum of the Revolution. Bring baseballs, especially Rawlings. Give them away.