Tmoney. The plus points of Italy are that a lot of people speak
English, boat kit (most of which is made in EU) is freely available from anywhere in EU without tariffs and there are lots of boat services. However,
mooring fees can be extremely high and there is a berthing (wealth?) tax applied to boats above a certain size, not sure the threshold or rate, look it up on the web. That said, if you have a
cheap mooring Italy would be fine and not a bad place to while away the time with an expresso while waiting for
service, but it may drive you mad!
If the mooring cost is prohibitive, there aren't a lot of low cost alternatives nearby, probably France is the best bet if you can find one. Port St Louis du Rhone specialises in cats and was reasonable but its a fair way away from Rome. Otherwise it would be
Tunisia but then the logistics for
parts will be a pain. Even in
Croatia with a massive
charter market and due to join the EU next year getting parts can be expensive and slow. My opinion is that you would be best to stay in EU while you are refitting.
The idea of getting a crew to sail the boat is sound but assuming you have very limited experience, you do need someone who can
skipper the boat and has experience of the
med and possibly an
atlantic crossing until you have gained enough experience yourself. There are plenty of qualified Yachtmasters, but far fewer with sufficient experience who I would trust and would be available for such an adventure. You would probably need a whole summer cruising the
Med to shake down the boat and yourself before thinking of the Atlantic.
The
project is certainly possible with careful planning - good luck