A lot of this answer depends on what you want out of sailing. One of the neat things about sailing is that it can be so many different things to so many different people. When people talk about ''boats to start on'', that phrase conveys a lot of different meanings.
For example, it could mean a boat for someone who is learning to sail or it could mean a boat for some one who is an experienced sailer but who has never owned a bot.
Assuming that you are a new sailer with minimal experience, that question leaves the door open for differing answers depending on your goals as a sailer. For many, learning sail simply means knowing enough about sailing to get the boat in and out of the slip and to sail and motor to where ever they want to go. They really don''t care about sailing the boat well and developing boat handling as sail trimming skills. (I am not putting a perjouritive sense to this.) If that is what makes them happy then more power to them. I have heard of people buying 50 foot boats and larger for their first boats. I say more power to them, and although they may learn a lot with a boat that size it is hard to really build sailing and boat handling skills on a boat that large.
If your goal is to become a skilled sailor, then I would suggest that you stick to a responsive, fin keel, spade rudder sloop under 28 or so feet with 25 feet being a bit more ideal.
That said, 28 to 30 feet is a nice size for a boat. It is big enough to offer reasonable accomodations, and depending on the design big enough to take a little bit of bad weather and also offer some decent cruising range. It is still small enough that you can manhandle the boat, the contol loads tend to be manageable and if properly designed is easy to single-hand.
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. . .
I am going to disagree with the others on this. I do not see a problem with learning on a 30 footer. I think the issue is money vs. time. Just because you have sailed a few afternoons does not mean you will enjoy sailing on the level of a boat owner. The big issue is time. Can you devote enough of it to make a 30 footer financially worthwhile. Bottoms need painting and repairing, teak needs tending, etc. Engines need maintenance. Unless you have the financial means to pay someone to do all this, it will mean a BIG time investment for you Bigger boat = more time.
Boats are slow to sell. If you get into a larger boat and find out it is not for you, it could mean a year or more before a buyer comes along. In the meantime you shell out for insurance and storage even you are not using the boat.
Small boats are cheaper in all regards - except they are harder to sell.
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.
Ahoy, YES/YES/YES, That said if you come any where near me in the first year I sink you you silly twit. Does a two you old ride a ten speed? Do we let 10 year olds drive? Is a thirty foot cliff to high to jump off with out a parachute? Really sometimes the simplest question has a simple answer. Big Red 56 And Im in a good mood I really am!