Driver, you''ve just heard it from someone who''s out there doing it. Jack is one of the most respected posters on this board. Last I heard, he was somewhere cruising around Europe..
Chartering boats really does nothing to help anyone actually <em>learn how to sail</em>, which is where you will want to start. You can put your money to much better use, and learn much more about whether cruising is for you, by avoiding the charter and geting on the hands-on learning curve.
I was in the same spot you are in, and I''m only a couple of squares ahead of you on the boardgame of cuising. I am at the end of the outline below, and feel quite prepared for my first "real" cruising sailboat. This progression worked well for me, and I recommend it to anyone.
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<li>Think daysailing first. You have to cut your teeth. Read books on basic sailing. I used Bob Bond''s <em>The Handbook of Sailing</em>, but any Barnes & Noble will have several like it to choose from. Pay special attention to sections describing reading the wind direction, the points of sail and basic sail trimming, and tacking & gybing techniques.</li>
<li>Read some other books.</li>
<li>Take that basic knowledge to the class Jack recommended. There, you will be able to apply all that theory. Your confidence will rise quickly. I''ll defer to Jack, but I think his reference to a one-person unballasted boat is just a <em>bit</em> narrow: a two-person daysailer would be just as acceptable as a trainer. But the idea is the same: keep it small and controllable so that you can learn. There is probably a sailing school or even a city recreation department in your area that will meet this need. Sailing schools sometimes will rent boats out by the hour to graduates of their classes; and if you sign up repeatedly at a rec. dept. class, they often will just "let you go" on the bay to get experience on your own once you prove yourself competent. This can be much cheaper than renting sailboats to get "stick time," and will likely put a few different boats at your disposal, but of course the trade-off is that you will have to conform you sailing to the class'' schedule.</li>
<li>Read more.
<li>If you have cruising ambitions, consider a "weekender" as your first boat. 19-23'', a cabin, and basic camping-like ameneties: a couple of bunks, small stove, ice chest, porta-potty. You can practice many cruising skills (anchoring, coastal navigation, reading charts, taking bearings, etc.) on overnight trips in a small boat that take you just a few miles from your home port, as your reading turns from general sailing to cruising advice and stories.</li>
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By that time, you will know if the call to cruise is a real tug at your soul, or was a romantic daydream better read about but left to others.