BA,
This could be a good trip for you. I don't know what your experience in making crossings are, but if done with forethought, can be great.
Pick up a copy of the Gunkholer's Cruising Guide, as there is good cruising info on ports, marinas, approaches etc.
I would run the first leg to Cedar Key first about a 70 mile sail. From there you can run close to shore and set your daily legs from there south.
This time of year, I would not recommend a straight-line trip. I have heard nightmare stories from some friends who did.
For me, I like sailing the days and anchoring in safe harbor at night. This will ensure enough rest, a good dinner and relaxation. You can bet the weather will throw some front your way during this, so shorter legs would be the best way to travel.
Set up your sail plan & log it with the Coast Guard. Give copies to your friends with call times each leg, & hopfully have an EPIRB.
It could be a gasser of a trip, keep us up on your plans pal......
CR