Learning to sail on smaller sailboats in a local lake is a great place to start. It is less forgiving so it gives you a better feel for the
wind and the efficiency with which you are sailing, and if you lose focus you end up in the
water. That is a great motivator.
I first learned to sail on the Charles River in Boston. It was the most challenging sailing I've done. On a larger
boat there are more responsibilities, and
mistakes are more costly, but the sailing part is easy.