Hi Redpaddy and Buzzcock,
Living in Melbourne, I'm used to long haul flights with work - so that's not a problem! It's only 22 hours or something... not that bad.
Pisa and the Dolomites - I will look into that! What do you love about Pisa?
As well as Castiglioncello. Thanks Buzzcock.
You know, when we stayed in Lazio, we were in this town called Acquapendente. We found an amazing little pasta store and were there for the Tuesday evening proscuitto carving. Amazing! It's those little experiences we love!
We're not big fans of visiting big cities during our 2 week trip - we met in Italy, we are looking at places we hope to retire and yeah, we like to get away from the really busy areas while on vacation. A small city is fine I think. Is Orvieto a city? Not sure.. but we love Orvieto. I'm just talking about avoiding the queues, the big ticket attractions.
It's utter madness to include the Dolomites in your itinerary as well! Two weeks is not a whole lot of time, plus keep an eye on the season: if you don't have experience driving in snowy mountainous terrain, november isn't without risks in the Dolomites.
As to the festivals, the Orvieto one is called Umbria Jazz. The main festival is in Perugia (also well worth a visit), but there are related activities in Orvieto as well. I can't find information on the one in Cortona (maybe it's not an annual affair), but its cultural agenda is packed for November anyway.
Good point about driving through the Dolomites - I'm sure it is different to driving through Mt Amiata like we did. Back in November in 2004, it was quite nice, but the Dolomites may be different.
I saw a potato and chestnut festival somewhere, as well as a bonfire festival. It'll be a fun trip!!
I concede our itinerary may be too crowded - perhaps we'll keep to Italy only.