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I went from Sunfish and Hobie sailing a few times per summer as a kid to bareboat charters in the Caribbean in my thirties and forties with nothing in between. I did well on the big boats but I knew I wasn't a good sailor. Those charter boats are such slow-reacting slugs that I never really knew what effect my actions were having. I was constantly over-correcting for the previous over-corrections.

Now I'm in my fifties and I want to become a good sailor. I bought a sailboat to learn the fine points. I went small mainly for $$ considerations and also I noticed that most of the bigger sailboats stayed at the dock while the little boats were out sailing.

What I've learned so far is: yes, small boats are much better teachers due to the instant feedback. They are sportier and I get more of the joy of sailing feeling in comfortable, light air conditions than I ever got on a big boat. But the biggest difference is the work and expense of boat ownership. I cannot tell you how glad I am to own a boat that has a simple rig and no auxillary systems like electricity and plumbing. Someday, maybe. But I'm going to learn all I can on small and cheap before I go big, complex, and expensive.

If your intention is to always charter and never buy, I'd tell you to go ahead and learn on a big boat.
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