>>2232523I grew up sailing and raced dinghies in high school. You should learn to sail in a class ideally or if there is a rental place that gives lessons. Rent before you buy, and if you are only going to use it once a month or so you are better off just renting if possible. A boat is basically a black hole that sucks in money.
My favorite dinghy was the Laser, which is great for one person, but you will want something bigger if you want to fish or transport useless passengers. A bigger sailboat is more difficult to handle by yourself but a smaller sailboat can be a lot of activity, so it really depends on what you are going for. Stick to something with one sail though unless you hate yourself.
