Transporting Mast on Boat
I used to routinely transport my NorSea 27 on its trailer. The mast was supported on each end by the bow pulpit and the stern rail. It flexed a lot as it bounced along the highway so I made a brace that looked like a giant slingshot and bolted it in the tabernacle where the mast mounted. That seemed to solve the problem.
I also left the rigging on the mast while transporting it. Just take a bag of wire ties and connect the loosly coiled rigging to the life lines so the wires dont chafe the fiberglass. When you get to your destination take a pair of diagonal cutters and snip the wire ties.
Bags of wire ties are cheap at costco.