re: Need advice - trip to Italy and Greece

Hiring your own sailboat and being able to do the Greek islands at your own pace would be ideal, imo. Everything is so relaxed there that you're not going to want to abide by some cruise ship schedule. Gives you the freedom to go where you want, when you want, and also probably see some ports that the cruise ships wouldn't be able to get to. Did a day sail from Naxos over the summer and it was the highlight of our time there. You might find it a little more complicated as far as logistics go, but the tradeoff would be more than worth it.