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The C250's windward ability with the wing keel is quite good; we never tried trailering the one we have. I guess it can be done given the right type of ramp, but it seems like it would be quite a chore to do regularly, though probably would be fine for end-of-the-season, or to go sail different places. The 250 is a very roomy boat for its size. There will definitely be a lot of info on trailering at the C250 forum. Can't really comment on the Hunter 25.
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