A gamble. You will likely be able to make the entire trip without any issue. BUT. You may also be unlucky and get stopped along the way and have to drop the boat, tow the travel trailer farther down the road, go back for the boat, go forward and hook the TT back up, and proceed hoping it doesn't happen again. Or really unlucky, may happen multiple times. I would avoid heavy travel times when traffic enforcement patrols are more likely. Have never double towed. But we have driven for hours at a time and never see an LEO. And other times seems there is one every few miles.