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Best Centerboard Designed Boats
I think the keel/centerboard designed, as mentioned above, is the best CB configuration. This design is used by Hinckley, Bristol, Little Harbor, Cheoy Lee (Pedrick 41) and Alden to name just a few builders. Many K/CB boats can be sailed equally as well with the board up as down, on almost all points of sail. Downwind there is the advantage of having the boat up, upwind, having the board down can be a significant advantage.
I would say (since I just got one) that the most beautiful and well designed K/CB boat of all time is the Hood 38 built by Wauquiez. Sisterships were built by Bristol (38.8) and Little Harbor (Ted Hood''s company). She is a delight to sail, very well thought out, well built and nicely finished. I could not be happier. Thus, I will recommend to you Ted Hood''s K/CB designs.
Perhaps one of the most significant advantages, aside from the obvious ability to sail into skinny water, is the wonderful tracking ability of these boats. This is not to be taken lightly if you plan to do some distance cruising. I can take my hands off the helm for long periods of time, not even bother to lock it in, and have the boat track on any point of sail.
To me, with a K/CB, you have all the advantages of a full keel boat and a fin keel boat with none of the disadvantages of either.
Maintenance is really very minimal and does not occur on even an annual basis. Just keep inspecting the cable when the boat is pulled. As to the placement of the winch for the cable, there are several different designs. Some use lines to the cockpit, some have a winch with cable in or just out of the cockpit.
I hope this helps.