How hard can it possibly be?
A lot harder than you think, man. This is the OCEAN we're talking about. Ask any fisherman in Mexico and he will tell you
exactly how hard it could possibly be. When Fidel Castro and Che Guevara invaded Cuba from Mexico in the sixties they used a motorized boat to get there, and the crossing took several days because of bad weather and they almost sank many times. By the time they finally reached Cuba they were so exhuasted that they were useless for the attack against Batista that they had planned, and would have probably been wiped out by his army if they hadn't been able to escape into the mountians.
A Lanteen rig is a triangular sail that was widely used in the Medeterranian, Egypt, and San Fransisco (on the Italian immigrants'
fellucca fishing boats) in the late nineteenth and early twentieth century. It is the most effective sail for beating against the wind and is very versitile. The rigging is a little complicated, though. Nowadays you mostly only see them in the Egypt and on the
jangadas of Ceará, in northeastern Brazil. As for the keel yeah, I would make a big one because if not you'll probably tump over.
Egyptian
Fellucca
Jangadeiros on the Atlantic Ocean, northeastern Brazil
I would not make one as tall as the fellucca, though. Make it shorter and wider. You should DEFINETLY hang out in Mexico for awhile with the fishermen and learn to sail before you try to go to Cuba.
Also, I'm almost positive the Cubans don't charge anything. They don't even stamp your passport so Big Brother won't know you were there. They want dollars to be spent there. It's the American government that gives us shit for going to Cuba.