Thanks for answering, dog.
The fairleads are on a track on the toerail. I don't see any evidence that they were ever located inboard.
Standing rigging has not been inspected since I bought the boat but will be sometime this winter.
, the boat wasn't raced, but the PO put a lot of cruising miles on it.
, the sails were covered when furled. The headsail is roller-furled with a sunbrella strip on the leech.
The boat was built in 1981.
I don't know how old the standing rigging is.
Originally Posted by sailingdog
The sails could definitely be the problem. Other things that could be part of the problem—where are your genoa/jib fairleads located. The further outboard they are, the less high you can point as a general rule. Has the standing rigging been inspected and adjusted since you bought the boat. A badly adjusted rig can have a lot to do with pointing problems.
I'd look at those three areas first, before doing anything else. The sails may be shot, depending on how hard the boat was sailed, and how the sails were stored and used. 11 summers under the Chesapeake sun without a sail cover could definitely cause some UV damage to the sails. If the boat was raced, the sails could definitely be stretched out of shape—same with the rigging. You don't say how old the boat is, or how old the rigging is. The fairleads, IMHO, are probably the least likely and least expensive cause to fix, unless a PO moved the jib fairlead tracks.