I've towed tandem many times. Illegal in many states. Mostly legal in states West of the Mississippi. The rear trailers wheel will follow the front trailers wheel exactly. I put the masts on the front trailer. The length is illegal in all states. The whole thing has to be under 65 feet. I love towing tandem. It's much more convenient for breakdown and setup. You have to get the tongue weight right on the second trailer. Too much and you pop a wheely on the first trailer. Also you would be surprised at the amount of distance you have to separate the two trailers. You also have to keep the masts high on the first trailer to keep them from hitting the second trailers boats bows. I even did a double one time with a tandem behind it. That was fun.