Join Date: Oct 2009
Location: Cape Cod
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Re: Are sailing schools worth it?
I think you can divide the skills into 2 categories: Sailing and everything else.
IMHO there's no better way to learn to sail than on small boats. When you trim the sails right, and balance the boat, they reward you immediately with increased performance. Big boats not so much. I've done some instruction in this category, and find that a little talking, and a lot of doing is the key.
On the other hand, there's all the other stuff. Weather, navigation, safety, COLREGS, anchoring, close quarter maneuvering of bigger boats, etc. I've had experience teaching this as well, and IMHO quite a bit of talking works here, and can help you not learn stuff the hard way, which is often expensive, and sometimes dangerous.
Cutting to the case, if I had $2K to spend, and just wanted to learn to sail, I'd probably buy a small boat and find a buddy with experience. If on the other hand my plan was to immediately start cruising distances, not just dipping my toe in the water, in a decent sized yacht, I'd recommend some instruction. For this lifestyle, you also need a budget for the next step beyond schooling, buying/maintaining a cruising boat, or at least regular chartering.
Good luck, but whatever you, give it a try. Most on this board would say that sailing is one of the best things that every happened to us.