Can you post the time and place so I can get out there withy my lawn chair to watch? (just kidding)
It can certainly be done but will not be as convienent. If there is a large rear overhang, the trailer will react far more quickly than with a truck and you will likley need more space to manuver due to the length of the combined rig.
I'm assuming the rig isn't horribly underpowered. It would be embaressing to not be able to pull the boat up the ramp. There should be plenty of traction for the rear drive wheels.