The Italian Waters Pilot and Greek Waters Pilot are very good and certainly worth a good look at even if you don't end up buying them.

As far as laying up is concerned, that's largely depends how enjoyable you want your sailing to be.

I did a delivery from the South of France (St. Raphael) to Greece this February and although it was cold and sometimes windy it was certainly sailable. I wish I'd had a lot more time to enjoy Sardinia and around Messina. The volcanic islands north of the Medina Strait are spectacular, night or day, if you don't mind clanging your hull between floating rocks in the tidal swirls.

Greece wasn't up to much at that time of year although I guess it was a novelty to be the only yacht sailing in the Ionian.