Good question, but unfortunately no simple yes/no answer. Most of the regulations for tandem towing are in the commercial portions of the Florida vehicle code and may or may not apply to private vehcles. I've read it several times and cannot say for sure, but it is clear that tandem towing IS permitted under at least some circumstances but with restrictions based on type and purpose of the equipment. It's all these restrictions and exceptions that make it all but impossible for a layman to tell. See Florida Highway Regs
On the Florida Turnpike system, a "Tandem Towing Permit is required and perhaps a CDL as well.
Tandem towing is prohibited on some local roads, especially residential areas. Weight restrictions also apply, e.g. bridge loads.
Maybe a call to the Florida Highway Patrol would get you and answer you could share with the rest of us? Call 850.487.3139 or email: firstname.lastname@example.org
2004 American Tradition; 2014 Buick LaCRosse
Homebase in the Ocala Nat'l Forest near Ocala, FL