We keep our boat in Northern Italy
. Furthest South we made it was Elba. Fantastic place. Lots of free anchoring
and beautiful. At first we avoided Portoferraio but ended up having a great time there. Good place to anchor
if you don't want to pay the dockage fees
but a night on the dock
is great fun and a fabulous atmosphere. Lights are out around midnight so you can get some sleep. Porto Azzurro is another fabulous spot but the anchorage gets really tight on a Weekend night. If an Easterly blew in there would be a lot of carnage. The town is great and caters to German tourists. Overall we had a great time. We provisioned at the local market. Cavo was really nice as well but there has to be some west in the wind
otherwise it is a nasty lee shore. Our first stop there was great our second we had to retreat back to Portoferraio. This year we are headed to Sardinia so maybe we'll cross paths.
As far as info on a circumnavigation
it really depends on your cruising style. Our first summer in Italy
we travelled a total of about 80km in 6 weeks. There was so much to see we stopped constantly and when we stopped we liked it so much we would stay. Hey there's a castle lets check it out. After that hike we would get on the boat and sail for 7 or 8 miles and then we would say that looks like a nice Church. and so on and so on. Last year was our second summer. We decided to sail harder. We sailed from La Spezia to Elba and back. A total trip of around 235 nm. Our boat only goes about 4 or 5 knots but we broke it up into smaller legs and had a lot of fun. The Italian Waters Pilot is a good source as well as these websites JimB Sail | Helping Skippers plan European Cruises
and Portoferraio update | Roaring Girl
. The latter is a blog so you have to dig for the info but it is entertaining.