Check the difference in cost. It may be that the leasing
company is charging more to cover more of the amortizing of
the boat plus insurance. In either event, the sailing club
is all but guaranteed to be a better environment for
learning to sail well.

The leasing company is definitely more expensive, but the boats are
also a lot more appealing to me. I just want to make sure I am not
being foolish by taking on a large boat with just a few days training.
What I would really like to do is go on a multi day trip, which the
sailing club does not make available.

Thanks to everybody for the feedback!