A third alternative that actually works pretty well for royalex boats is to tie one boat on as normally, gunwales to rack, and then stack the second boat on top, gunwales to the sky. Thread the bow painter of the top boat through the grab loop of the bottom boat then to the bumper/frame or whatever. Tie the sterns together, too. You will also have ties from the racks over the top of the boats, a pair for the bottom as normal and a longer set across the top boat. The top boat may move a little, but it isn't going anywhere. If one boat is longer than the other, the long boat goes on the bottom.
An option with this set up is to tie a Santa doll sitting in the seat of the top boat. I've never done it but it'd be sure to get some grins.
URCHIN Portable Anchor
4-place Boat Trailer
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