I don't know if it's legal in Florida, but I do know I have seen many large RV's in Florida, towing a large vehicle (I once saw a full size Hummer being towed, with a pontoon boat behind that!) and a boat behind the vehicle, behind the RV! I thought it wasn't legal too but I've seen plenty of them down here. Lots of "double" trailer UPS trucks too.

BTW, I was not trying to blame the driver in the above post, we don't know what happened, maybe someone cut him off. I'm just saying when it gets windy or wet, or both, I always slow down.

I did tow a 25' long box trailer once, with an airplane inside, and it was fine up to about 65mph. As soon as I got much above that, and on a dry road, it would start to sway, and the longer I let it sway, the larger the occilations got. Needless to say, I didn't go over 65 after I figured that out.

And someone up above mentioned cruise control on a wet road. I had a scare with that once too, so now I don't use the cruise when towing unless the roads are dry. It can cause the tires to break loose on a wet road and that can get sporty.