Sailboat trailers come up from time to time on craigslist. About half of them are sketchy home-built things though. So far, I haven't had the spare cash handy when a reasonable one turns up.
Flat-bed "car carrier" trailers are much more common and some of them have the load capacity for a sailboat. I already had one, so I built a cradle for the boat and chained it to the trailer with load-binders. Plus a few extra boat stands. There was considerable over-hang, fore and aft. I had to carefully work out whether there would be sufficient clearance for the tow vehicle at all angles. The flatbed truck worked well, but there was not enough clearance to use the suburban.
This also required an over-sized vehicle permit, which was not difficult to get (through a trucking agent - not through the DMV office.) If you have to traverse more than one state, an agency is the only way to go. Maybe not needed for an E27?
Of course, one drawback to this is that you then cannot use your flatbed trailer for anything else while the boat is sitting on it. I have imagined an all-steel cradle that one could jack up onto outrigger legs (like a fertilizer bin) and drive the trailer out from underneath. Then jack the whole thing down to the ground. So far it's just an idea though.