Can be done, but,
I have my C27 on a trailer and use it as a trailer sailer. The biggest concern is the weight facter, are you aware that the boat and trailer combination will weigh in at least 9000lbs? Unless your going to use it as trailer sailer, I don't think it's worth the effort. Besides need a very powerfull vehicle and a trailer with sufficient braking power and other specialized equipment, you will also run into legal issues such as road restrictions. The beam of a C27 is wider than permitted on most hi-ways necessatating the acquisition of road permits something that may not always be obtainable. For a short oneway haul like you are talking about, I would recomend contacting a local trucking firm.