That will be quite a trip.. maybe Cuba will be "cruisable" on your way up !
as you know, January around Tampa Bay can be quite "blowy" and cold when the fronts come by.. ya might have to hang out in Key West or Havana waiting for a weather window.. This is from the planning section of The Accidental Cruiser:
[From December until early April, frequent cold fronts penetrate well into the Caribbean. Winds ahead of these fronts tend to be easterly at 15 – 20 kts. Behind these cold fronts, winds are mostly NE 20 and sometimes stronger, with 2 – 3 metre seas. The winds behind the fronts sometimes blow for several days until the next cold front approaches. It is possible to make a passage between fronts, but the position and features of the Gulf Stream current should be monitored to ensure a smooth passage. Wind against current will produce large steep seas. Rain, gusty winds, and occasional thunderstorms are often associated with cold fronts./COLOR]