A few comments and suggestions.
First and most important. Do not get too focused on a schedule. That is one of the easiest ways to get in trouble. Especially this time of year the cold fronts can blow through S FL often and cold fronts usually bring strong winds and nasty waves in the Gulf Stream
. Check the weather
carefully before you go AND do not hesitate to turn around a come back if it is rougher in the ocean than the forecast
is not an exact science and the wind
and waves 20-30 miles out can be much worse than the report.
Second, with your boat if conditions are calm enough, you can make that trip in a couple of hours. Even if you lose one engine
and can't get up on plane you are still only a few hours from land. If you want to be really cautious take a couple of portable tanks
to feed the outboards in case your main tanks
or lines have a problem.
I assume you have a good VHF radio
. If not, get one. What about a towing service
? Get the BoatUS or Seatow unlimited package.