Join Date: May 2002
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As boats increase in size they increase rapidly in the difficulty of trailering. A deeper keel (4' or more) is often more difficult to launch because it requires a launch ramp that will accommodate it, and sometimes such a ramp can be hard to find. Also, bigger boats have taller, heavier masts. That means that, while they are capable of being raised and lowered by a single person or a husband and wife, if you have a mast-raising system, they are nevertheless more difficult to raise and lower without help.
Years ago, I bought a Catalina 25 with a 4' deep keel, with the intention of trailering it alot, but found that it was difficult enough to trailer and launch that I only trailered it on rare occasions.
We all have different standards, but by my standards, almost any sailboat over 25' will either be difficult to launch or difficult to raise the mast without help. If you need help from a marina to either launch and retrieve it, or to raise and lower the mast, then trailering can become expensive. Smaller boats are easier to trailer and launch, but they generally have more cramped accommodations. It's always a compromise.
I finally decided to sail my Catalina 25 from a slip at a local lake during the summer, and then bareboat charter a bigger boat for my vacations. It's nice to arrive at the marina at your vacation destination and to find the boat clean and ready to board and sail away. Sometimes it's also fun and a bit less expensive to share the cost of chartering a bigger boat with good friends or relatives.