What engine & transmission?
You'll have a lot better chance of having your question answered correctly if you specify the make & model of the engine/transmission. I don't know abt. Hunter 33's specifically, but most boats were available with a variety of different power options, some of which were tolerant of allowing the prop to freewheel ( trans in neutral) while others will self-destruct due to lack of adequate lubrication.IMHO, you're better off to not allow the prop to rotate when sailing.