Best Answer - Chosen by Voters
I have never done this, but I have heard of people doing this. It takes planning, two or three people, and knowing what you're doing around jacks. Here's what they did:
Jack up the boat sitting on a trailer using a hydraulic jack and wood blocks for support and to protect the hull (not just from scratches, but to spread the weight across a larger area) simultaneously at six or eight points.
When the boat is above the trailer, s-l-o-w-l-y pull the trailer forward until the trailer's cross bar almost knocks your supports down.
Start a new jacking point.
Repeat.
When you're finished, the boat will be sitting on the blocks, and you can then back an empty trailer under the boat using the same technique in reverse.
Good luck!