I believe that the C 27 is more then 8.5 feet wide, closer to 9.5 feet wide, so it is not legally a trailerable boat on U.S. roads, wthout a special use Wide Load permit. You would also need an F 250 or heavier vehicle & a double axle tandem trailer, which are expensive & hard to come by. As with any boat, in blue water sailing bigger tends to be better. Its the simple matter of having enough lead under you to help keep you upright, enough beam & freeboard to help keep you dry, and enough length to keep the boat from pitch polling non stop in big wave action. There are sailors who have taken 22 foot boats almost everywhere, such as the venerable Trekka (22 ft). There are also morons who have sunk 50 footers who were not competent sailors & didn't know their limits. A young sailor, Matt Rutherford just sailed around the Northwest Passage, down to S. America, around Cape Horn & circumnavigated the Americas, solo non-stop. This was in a 1970's 27 foot Albin Vega. Pretty impressive, & maybe a little fool hearty. But this was in a Scandanavian designed boat built for blue water sailing. While I have owned & loved all Catalina's the 22, 25 & now a C 30, they are all built on the light side & were all designed for fresh water or coastal rated cruidsing. You have to know your limitations & your boat. Go out & sail her locally in heavy weather, with at least 5 foot waves & 25 + knots of wind, & then decide if you & your boat can handle what could easily turn out to be TWICE this on an atlantic passage. Then you have your answer.