Yes you can trailer a 27. Be aware that the beam of the boat is greater than waht is allowed without a wide load permit. (Doesn't mean you have to have one, but!!!) Trailering requires a healthy towing vehicle. I use a Ford Power Stroke in a 3/4 ton 4wd supercab. This is definitely enough truck to handle the rig, as I have taken it over the continental divide in Colorado. If the boat doesn't have a hinged mast step, you should plan on replacing the step with one that does hinge. (Not expensive) Time should be spent learning how to raise and lower the mast without the aid of a crane. It really isn't that hard, but you need to understnad the principles involved. Join the Catalina 27n list which I found through the IC27A, which is the Catalina 27 Association. Ask questions, as this has been a topic of discussion in the past, and the answers are there. As I live in Colorado, and ny C-27 is my third sailboat, I have experience with the problems associated with trailering. Feel free to e-mail me when you are ready to try raising or lowereing the mast, and I can provide a detailed description of what to do.DanCorsairC-27 #2262