Fellow Pilgrim Owner here -
My loaded (on the truck) height measured out at just about 15.' As PMF 1984 stated, the fly bridge will have to come off if the boat has one, as well as everything else on the boat (top) deck. In my case that was: fly bridge; mast; radio antennas; the fake stack; dinghy and davit; solar panels; all railings down to stanchion bases. If you have a fly bridge and steering & engine controls up there, it's a bit of a challenge disconnecting and stowing the loose ends for the move, but doable.
Everything stowed on or in the boat for the move except for the fly bridge. I had to remove it and brace it with two 2x3s, and the mover was able to carry it on the tongue of his trailer. I'll try to post a couple of photos; if I can't, but can answer any other questions about my experience, email is firstname.lastname@example.org