SUggest you focus on giving the wife and family
a nice time, and concentrate on one or two countries, many charter companys will limit your distance away anyway.
Bear in mind that in the med in peak season , marinas
are crowded, unavailable or very expensive, especially so for Cats. I would avoid France. italy and spain for that reason, and consider 4-6 weeks in Greece, Ionian
for light winds, Cyclades
for more adventurous stuff. Cats are available but not common in the med. ( much more so in the Carribean).