I would like to point out that Cuba and Belize are not part of the Gulf!
When you say circumnavigate the Gulf, are you including the Mexican coast too?
I understand that Belize is not in the gulf, however wouldn't the line from Key West to the western tip of Cuba to the Yucatan Peninsula mark the boundary of the gulf? And yes, including the Mexican coast as otherwise it would be too long a span with out rest stops. I know that at my age and condition, more than two days and one night of continuous sailing would be too much.