Buckeye...I think I would just head down to th Dry Tortugas and make the jump in settled weather to Isla Mujeres, then work my way down the coast.
With a bit of preparation, that shouldn't be too difficult a trip ...3-4 days off shore, then coastal work. Assumes you have a reliable engine and autopilot if you're doing this alone. Do it AFTER the hurricane season and before the northern fronts start making their way down into the gulf. That means early November. If you can't leave then...do it along the coast.
Try Steve Pavlidas' new guide for tips, chartlets etc. Here's an example of how good his guide is:
(darn system won't let me post a clean link...just add the www)
No longer posting. Reach me by PM!