Combining a lot of entries into one is hopefully ok.
I have been skipper for member sails on https://www.downtownsailing.org/ dayfleet boats -- J22s and Sonar 24s -- going out nearly 30 times over the year so far. Sometimes it was with experienced skippers, sometimes with people new to sailing. When winds permitted, we would make it to the (remains of) the Key Bridge, but otherwise we would sail around Baltimore harbor in the local varied winds. We would practice techniques prob POB drills to using the traveler. Much fun was had over the year.