We got stopped while double towing our boat we kept in Clewiston, FL of all places right on Long Key Bridge going to Marathon (Florida Keys) in the mid 1990's by a Monroe County sheriff. His first words were "do you know how long you are? "You looked awful long". In my mind I was thinking, of course I know, stupid, but I didn't say it. He got his wheel out of his patrol car trunk and fumbled around for a long time and then measured our rig twice. When he came up to me I said it's 64'11" long and he said "well I get 65 feet". I said 65' is legal in Florida and he looked at me and just said "have a nice day and drive safely" and got back in his car and did a "U" turn right on the bridge and took off. Now a long line of traffic stopped behind us. What a jerk! He didn't even notice my truck plate was expired but I did and had the dealership overnight a new plate to us as it was leased to my engineering business and back then the dealer had to get the new plate each year in Michigan.
BTW, we just got back home April 7th from Florida's west coast going on 19/98 and I-10 and up thru thru Alabama on 231 and I-65 and saw over a dozen double tows in Florida and Alabama both. 3 on Dothan Circle. All were 5th wheels and mostly with boats in both Florida and Alabama and ZERO pulled over. We see them every year all on our way from Michigan down to Florida and again going back north. Never seen one double tow pulled over yet the last 15 years or more. We'd kept a 16' on up to 22' boat in Florida for 19 years so we didn't have to double tow one back and forth.