Just about any boat should be able to point about 45 degrees off the apparent wind. However, that doesn't mean you are actually SAILING that close to the wind. For example, my O'day 35 has a shoal draft and a fixed 3 blade prop. If I try to point very high, the boat makes a lot of leeway and basically slides sideways. The shoal draft keel prevents my boat from sailing at high angles. About the best I can do is 50 degrees (tacking about 100 degrees).
A boat that I race on, an early 80's C&C 34 with a deep draft keel sails much closed to the wind. That boat can point at about 35 degrees apparent (about 45 degrees true) and actually sails that high.
I do not profess to be an expert, but things that affect how high you can sail are the keel, rudder, prop (less drag allows you to sail higher), sails, and hull shape.
If the bottom of your boat is foul with growth, your sails old and bagged out, and a traveler that doesn't work right, you are never going to be able to sail high.
Clean the bottom, make sure your foils are clean and in good condition, check your sails. When sailing as close to the wind as possible, make sure you trim the headsail in as tight as possible, and after the main sheet is as tight as possible, use the traveler to get the main up to center. That's about as good as your boat will do.
Day To Remember, 1986 O'day 35 For Sale
Deep Blue C, 2002 C&C 110 For Sail
Mt. Sinai, NY
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