I agree with Jeff: 30 ft. would be an outside maximum. Smaller boats will let you develop your skills faster and better. Even a 27'' sloop will make you a better sailor after one summer than a 30-footer will.
My friend owns a Catalina 34. I''ve been out with him for several summers, and he let me do just about everything there is to do. But I learned more, and learned it faster, on my own Catalina 22 with an outboard. And I loved every minute (almost) of it. All that experience is directly transferrable to any boat I sail, because the skills I learned were foundational do sailing.
Now that I''m a bit seasoned, I''m shopping for my next boat, and it will be around 30''; my first real coastal cruiser.
If you''re bound to start off with 30'', then read, read, read, and make every daysail an opportunity to practice some skill: anchoring, changing sail underway, heavy weather sailing, piloting, helmsmanship, etc., or you will be like a teenager driving a Cadillac. The last thing you want is for your new boat to get away from you because you were caught at the bottom of the learning curve with too much boat around you. Insurance only does so much, you know. . .
Zach, this has been a frequent topic on these boards, so here are my 2 cents from personal experience.
I recently bought my first sailboat, a 35 footer, with which I''m learning to sail. My sailing experience is mostly limited to crew on a Schock 35 and Catalina Capri 26 for a summer of beer can races. The Catalina taught me only that I didn''t want a small, very slow boat.
I bought the larger boat for speed and comfort. I have a large family (3 daughters, wife, nephews, neices...), many friends and business relations in San Diego, so 33'' seemed like a minimun LOA for me. There are more modern, smaller boats with huge beams that are roomier, but they were out of my price range, or not well recommended.
The first shock of the larger boat was the much larger loads on sails and rigging, and much more powerful forward inertia. Much more care must be taken around loaded winches, sheets, etc... The second shock was the first time the boat got a little out of control in a freshening breeze. Beating across San Diego bay in 20 knots true, with a rail in the water, limited room to manuever, no experienced crew, while trying to remember all those tips on how to blade out the main and genoa, was like taking horseback riding lessons at the Rodeo!!
ON A LARGER BOAT, IF YOU HAVE LIMITED EXPERIENCE, YOU MUST HAVE AT LEAST ONE EXPERIENCED CREW!
Oh yeah, the point. If I had to start again, I''d have taken lessons at a sailing school on a J22, C22 or something like that. If you''re young enough and don''t mind getting wet, do some dinghy sailing. I would also immediately join a one design sailing/yacht club, even if I didn''t have a boat. Lots of sailors talking and doing lots of sailing.
A 30'' sailboat is just fine to learn on. I will take a bigger boat anyday. The bigger boat will be safer with a slower motion.
The problem with say a Catalina 27 is that while it does the job it''s just a little too small for a man to stand up in and a family to enjoy crusing. So they are only kept 3 years on the average. A 30'' boat can be a keeper for coastal sailing.
Never mind the "learning the little nuances of sailing from a responsive boat". You can buy just that one boat and motor around with it and learn to sail a little at a time.
Ruskin wrote an essay on the fact that the most expensive thing that you can buy is something that fails to do the job you got it for. Buy the 30'' or bigger and forget the little boats.
I started with a 25'' and got rid of it in 3 years and got the 30'' I kept the 30'' for 18 years. That''s what I mean. Now I single hand a 35''. Not a problem.
I don''t get the comment above about needing a crew on a bigger vrs a smaller boat. A single hander does things in time, one at a time. Heck girls sail 60'' boats around the world! It''s not the size of the boat.