How not to tow a boat.

The right way would have been to lift the boat, and then put it on an adjustable boat trailer. That would have taken some skill though. Much easier for the local tow guy to drag it up on a flat bed and strap the h3ll out of it.

A sailboat as is pictured is best hauled in a keel cradle with the proper trailer. The cradle is typically built with heavy lumber (6X6, 4X4, and such). The keel is not so much supported as is shown with the DIY trailer but the hull takes most of the weight onto the cradle.

The cradle trailers are simple, two (or more) steel cross supports that are slid onto parallel rails. The parallel rails comprise most of the trailer. The trailer I used had active hydraulics to lift the cradle from the ground for transportation.

My longest sailboat haul was from coastal NC to St Paul, MN and was an adventure. Weather and the small truck I had, made for a treacherous ride. Also, I was over height, over width, and was permitted for the entire haul.