One option you may want to look into is taking a "bareboat" charter from a flotilla company. I did this a number of years ago in the Greek Islands. Having paid a small premium for the "bareboat" option, we started out with the flotilla where we got advice on harbors and anchorages etc, got briefed on how to moor in the Mediteranean using stern
anchors. If I remember correctly we stayed 24hrs with the flotilla, after which we broke away as we wanted to explore further than they were able to. Towards the end of the charter we met up with them again on our way back to the base. We found this arrangement to be very satisfactory. We had the freedom that we wanted, but with the comfort of knowing that at any time we could call the flotilla skipper and engineers for advice or help.