Originally Posted by funsailthekeys
I have had to make the trip in the winter before and it was ROUGH. If you are going to go I would travel along the Mexican,Belize, Guatemala, Costa Rica, Panama, Columbia coast. The reason is that you can travel in the weather windows with a place to hide out in between. Also if your navigation is good you can travel behind the reef line in windy weather to stay out of the slop. Lastly you can plan your fuel stops better since it is a motorsailer. The trip is a little longer but lots of nice places to see. Personally I going to Belize in the middle of April of '09 from Florida.
That was how a friend of mine did it about 24 months ago. Seems the easiest path for that time of year.
I will say from a lot of personal experience in the gulf in the winter, a January/Feb crossing in the gulf is the absolute worst time to do it. I have been caught in nasty (read: unpredicted) storms. Some good freinds of ours spent three days heaved to before giving up and limping back. The other two (and the one I mentioned that hopped to Columbia) said they would NEVER do that crossing in winter again.
Just fyi. But the info FSTK gave seems about as right as it is going to get. Good luck on your trip.