There is a something very appealing about walled hill towns. There is nothing like your first hill town, for us it was Orvieto (on a previous trip). I have seen several hill towns described in travel books as the perfect hill town. You need to have walls, of course, complete if possible but few are. They have the twisty, little streets, churches, beautiful views. We stayed in a near-perfect hill town in Croatia.
We started this trip with five days in Spoleto which is a very nice hill town. Later we spent three days in Urbino which is the only hill town in Italy (they say) which doesn’t have urban development around it, although there seemed to be a little.
But there is a sameness about the hill towns and the streets are awfully steep when you walk around, and space is always at a premium. And there are usually lots of tourists at hill towns because everyone likes them. Anyway we decided to skip Siena. It just seemed like it would be too crowded and too much the same.
We enjoyed the Adriatic beach towns that we stayed in, especially Senigallia, so we decided to drop off the car in Siena and immediately take the train to Lucca.
Hill town pix: the steep alley up to our hotel in Urbino:
The hill town of Castelina in Chiati, near Siena: