As a Floridian, I'm excited about this. From a Cyclist standpoint, I'm really excited.
For the unaware, out of Fort Myers, FL (Gulf Coast, north of Naples, south of Tampa), there is a ferry service that goes to Key West.
It's about 150 miles, 3.5 hours. I've done this trip probably 10 times. They put on a movie and you space out for 3-4 hours. They also serve alcohol on board, if that's your thing. This trip is $120-150 for a round trip ticket. Best part? You can walk your bike right on board. I think it's a $10 charge.
Seeing as there is already a ferry port in Key west, and is only 90 miles to Cuba, I can see a $300 round trip ticket with a stop in key west to refuel. Sure it takes a day to get there, but if you were going for a two week trip, a stop in key west for a night aint the worst thing. Besides, how cool would it be to bring two bikes, and mountain bike in Cuba too?