Considerations for the Gulf crossing and Winter itinerary

We are hoping to cross the Gulf of Mexico in the next week or so, this will give us some time to explore the Florida panhandle of which neither Jim nor I have seen.  We will travel via Orange Beach, Pensacola, Ft Walton Beach, Destin, Panama City, Port St. Joe, Apalachicola to Carrabelle where we stage ourselves for the Gulf crossing to Tarpon Springs.  Staging, this is where we wait for a weather window to cross 160 miles of open water, no stopping a straight shot so weather needs to be ideal.  When at the staging area there will be others waiting for the go to cross, this is where you will be matched up with other boats to cross with as some boats can move faster than others.  The crossing WILL include night travel, some boats may take up to 22 hours to cross while others can do it in say half the time, we are somewhere in between.  We certainly can do it in say 12 hours but that may or may not be a comfortable speed and we will still have to deal with the crab pots, at the beginning the pots are not as much of an issue so that's where you would leave at night.  Then the next consideration is you must be 30 miles offshore of Tarpon Springs in daylight so you can see the crab pots, BUT, it is advisable to not get there until after 10am as the sun will be in a position to blind you from the glare off the water.  So much to consider, I guess, in the end, once in the staging area we will see who our boat buddies will be and go from there. 
Once across, we will travel the west coast of Florida to the Keys during the remainder of Dec and get to the Key sometime in Jan. We will have company to share this leg of the trip to the Keys, from there we are hoping to cross our wake in Stuart sometime in Feb.  For our non boater friends, crossing your wake is when you arrive at the place you began.  This will be the completion of our loop and where we take down our white tattered burgee and replace it with a gold one which now signifies to other boaters we have completed The Great Loop. 
Whats next?  Possibly a trip to the Bahamas, a (70 mile trek) for a few weeks in the Abaco's and Exuma's.
But 1st we need to get out of  AlaBAMA which we hope to do today!  Florida here we come, time to get the sunshine on?