Packing Gland and Ice Box
Check your packing gland.My '82 27' had a continually wet bilge until I had the packing glad re-stuffed with Teflon packing. A few drips mount up and a sail can get everything shaken down to the bilge. Now I get some water in the bilge, maybe a cup full, after a sail if the water was choppy and wind was good, I think most it probably comes in the bilge pump overboard drain and the rest from the few drips necessary for the shaft to turn. I sponge it out after a sail and now it remains dry as a bone.Also be aware that the ice box drains into he bilge, it is not too well insulated and ice melts quite fast, did you have ice in it during the summer?