We trailered a Cape Dory 25D from Wisconsin to Key Largo. Many 25D's came with a very nice Triad trailer. The total wgt of boat and trailer was about 7,000 lbs and the beam is 8'0" so it was not that big deal of to trailer it with a decent pickup. We usually launched ourselves (used a trailer tongue extension) but used a travellift to put the boat back on the trailer to make sure it was on the trailer pads perfectly. Took 2 months off of work and cruised the Bahamas down into the Exumas. I can highly recommend doing it--it was a blast. FWIW also met a couple who trailered their C&C 30 (not the mega) from the Maryland to FLA, but they had to get permits for overwidth, etc.