Re: Chartering smaller sailboats? Where?
I am no expert, but I think you will find this difficult, because:
(1) charter companies tend to only charter new/newer boats. I am sure there are exceptions, but the main reason why is that older boats have older parts, and therefore carry an increased risk of breakage/maintenance. Charter companies don't want to deal with that (both in terms of time and expense).
2) Charter companies tend to have larger boats. 30' is generally the minimum, often the boats are lager. This is mainly due to supply and demand; the demand for chartering a 27' is low; generally people want to charter 32'-low 40s' (based on anecdotal experience). And, of course, larger boats are more expensive to charter, thus more profitable....
I think that your best bet would not be to try and charter a boat, but to go to local yacht clubs and ask around, An owner would likely be willing to take you out to convert you to his "cause"!