Chartering in Cuba????

[mdsdurango]

Hi again,
I'm not a frequent poster on these forums but when I need some advice or opinions this is my first (and mostly last) stop. So I thank you in advance for the knowledge I gain from this forum.
My "crew" has decided that we should go to Cuba. So let's start there. Here is what I have so far;

1) Travel; We live in Colorado. It seems we can get to Cuba via a charter flight (including visas) out of Miami. The sketchy thing about that is they only sell tickets two months in advance, meaning we loose our entire plan and deposits if that plan falls through. Or, we can go to Mexico and fly from there. I travel to Mexico on business frequently enough to purchase tickets further in advance.
Is it still illegal to go to Cuba from the States? Plenty of people seem to have done it without serious consequence. Am I being foolish or taking an unreasonable risk to even consider this?

2) Sailing; I can charter a boat with Dream Yacht Charters in Cuba but I have to do it through their French office. The charter marina is in Cienfuegos. I have reserved a 52' fin keeled monohull. Will the draft of this big a boat be a big problem? Would a Cat be a better choice for the south coast of Cuba?

3) Timing; we are looking to travel the first week in December. Is this a good time to be sailing the south coast of Cuba?

4) Experience; I've sailed inland my entire life but my salt water experience is not vast! I've passed the classes through bareboat and advanced coastal cruising with both US Sailing and ASA and chartered nine days in the BVI's without incident. Crew is less experienced than me but proved capable on our BVI charter.

What am I missing? What should I know? Am I aiming over my head?
What about Weather? Tides? Currents? Politics? Visas? Returning to the States?

I know I am asking a lot but I am stepping into what is for me uncharted waters! Any advice is appreciated!

Mike