The sailing holiday season in Italy stretches from the beginning of May to the end of October. Peak period months of July and August are the hottest, but also have the lightest winds and the largest crowds. As mentioned above, the benefits of sailing in Italy is well known to Italians so bays and moorings can get crowded throughout these periods. Do also be aware that you can be paying up to €200 per night for mooring fees!
Direct flights available from many UK airports to Pisa, Naples, Sicily and Sardinia make chartering in Italy readily accessible.