The old Catalina 27 could be trailered and many were sold with trailers. The thing you have to look out for is the load width limits and height restrictions. Many states have an 8 foot load width limit. If you exceed the limit you have to have a permit, pilot car or both. There are also some special rectrictions on daylight only vs. night towing. Some states restrict certain times of the day, holidays, ect. It sounds like you will have several states to worry about and maybe you will need to do research on each state to be safe. Your pickup sounds like it would handle the load. If you haven't looked into trailers yet, you may want to consider a 5th wheel arangement. This would allow for the load to be distributed a little better and not work the pickup as hard. Brakes are also very important. Try to stay clear of the "surge type of brakes. I burnt up a set of brakes on my C 25 trailer when I had to go down a long steep hill. Good luck and enjoy.Bob Teeter