I have done the reverse: Miami
to Tampa via the keys and Tampa to Galveston.
rigs are plentiful, but at least in those deep waters they all are big, manned and are well lit at night unlike the shallow water
rigs. Also watch out for sesmic survey
ships. We were hailed by the picket boat for a fleet of seismic ships and had to alter course for a few hours to miss them. Also came across one lone fishing trawler
way out in the gulf.
Keep your radar
on all night and a good watch.
But do stop in Key West
for a few days of R&R before continuing up to Miami.