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How big is too big to start out?
I''ve followed this thread with interest, and since your situation is somewhat like mine, here are my two cents:
1) Think like a hermit crab: you will own a succession of boats, and will trade up as your needs change. Long-term thinking must prevail here. You won''t be the same sailor in five years that you are today. The idea of having one boat for your lifetime is romantic, but impractical. What you need NOW is something to do your basic learning with. Therefore,
2) Buy a trailer-sailer. They are usually in the range of 18-23'', and have several advantages:
(a) they are small enough to force you to really learn the basics of boathandling, and those foundational skills will serve you well when you move up to something larger. I can''t overstate this point.
(b) they offer good economic leverage: stored on the trailer during the off season, and waiting anxiously in a rented summer slip for you to get a hankering to sail. This way, you can be out on the water 45 minutes after you see the breeze on Saturday morning, because your boat is ALREADY in the water, the mast is ALREADY stepped up, and all you have to do is grab your sunscreen and car keys. And in the off-season, storage on the trailer is cheap. A big back yard is ideal; but even renting a space in an RV yard is less costly than renting a slip for the 8-9 months when you''re not likely to sail. I''m on the west coast, and I can''t imagine your sailing season is longer than mine is here in southern CA. Renting a summer slip/storing off-season is the best way to go, and the trailerable boat with a swing-keel is the way to do it.
2) Starting off with a trailer-sailer avoids this talk about hoisting, locations, costs, and inconvenience.
3) Trailerable boats offer the best of both worlds for a first boat. They are small (responsive) enough to put you on a good place on the learning curve, so that you don''t imagine you know how to sail standing behind the wheel of a 34-footer. The smaller boat will humble you and teach you. Jeff is right: there are plenty of guys out there in larger boats who don''t know much about sailing. And the smaller boat is still plenty big enough for week-end trips for two, or even multiple-day trips when you get adventurous (I cruised the coast of CA for two weeks in my Catalina 22 a couple of summers ago).
4) These trailerable boats have TILLERS. You learn faster by handling a tiller than you do holding onto a wheel. You get feedback from the boat through a tiller that you just don''t get (or aren''t experienced enough to detect) from holding onto a wheel. I''d never put a beginning sailer behind a wheel, if there were a boat with a tiller available. It''s a better teacher. You will wind up ahead of the game in boathandling skills by wearing the varnish off a tiller.
You will know automatically when it is time for something bigger. I''ve spent four seasons with my swing-keel trailerable, and now I know I have the skills AND the desire for something in the 30'' range. But I wouldn''t trade my "training seasons" with my current boat for anything: that''s the boat that made me a sailor.