Hill Town Itinerary

Everyone is different in what they like. I think Orvieto merits more than a few hours if you have the time. Assisi to me is one of the most beautiful cities- everything "matches". While I spent a couple of days there and also visited Perugia and Spello I would skip Perugia and spend the whole day in Assisi. There was a lot to interest both my husband and I in Assisi and really liked the church just down the hill Santa Maria degli Angeli which has the original church of St. Francis.

I'm still hoping to get to Cortona later this year.

Day 2 sounds like a lot. Over an hours drive to Montalcino from Montepulciano. Two stops is enough for that day. Did Cortona on a prior trip. Lots of tourists looking for "Under the Tuscan Sun" and I hear that there is only a wall to see. Very hilly town. OK if you have the time to kill. Would spend a full day in Siena and not split it and forget about Cortona. Or better yet, go have a long lunch at la Porta in Monticchiello. Here is the link to their place http://www.osterialaporta.it/en/ . Very small with absolutely wonderful food and great wine list! Need reservations. Beautiful drive from Montepulciano but best done in the day light (narrow road with lots of curves). Enjoy

We have done your Day 2 many times. It is a lovely drive and we've always had enough time to stop in Pienza and buy sem pecorino. I love the smell in those cheese shops! San Quirico is so cute, but Montalcino is our favorite place to stay in Tuscany. You might take time to pop over to the Abbazia Sant'Antimo just outside of Montalcino. There's a good restaurant up the hill from the abbey where we've lunched on the terrace.

Thanks for everyone's thoughts!

We aren't worried about Day 2 so much because most of the day will be spent in Montalcino, with a possible quick stop in Pienza and shopping and dinner in Montepulciano. Last visit to Italy we did Monte Oliveto, Pienza, and Montepulciano in one day (from our base in Siena).

I think we might skip Cortona, as I couldn't find a lot to merit spending an entire day there (while we love just wandering little cities, we want to really make sure we're spending our time wisely).

I like the idea of staying the day in Assisi and maybe just stopping in Perugia for dinner or skipping it altogether. Hubby is also interested in traversing Monte Subasio (weather permitting) to visit Eremo delle Carceri.

We'd love to spend more time in Orvieto, but I'm not sure it will happen this trip. We have a long drive from Rome to Montepulciano... but we plan on coming back to Italy many many times more because we have a long list of places to visit!

Now I have a whole day left to plan.. love finding new places to explore!

Would you consider taking the train to Orvieto and picking up the car there. I know there is a Hertz office across the street from the train station and next to the funicular that takes you to the top of the hill where Orvieto is located. We drove from Montepulciano, dropped off our car in Orvieto, stayed there 2 nights and then train to Rome and it was very easy. Never driven near Rome.

We considered the train and still may but we've driven in Rome (it was an experience) and since we're getting to FCO at 7:45 am we figured it would be easier to get the car there. I'll do some more research though :)

Thanks to everyone's suggestions, I've reworked the itinerary a bit -

Day 2 - Abbazia di San Galgano, Montalcino
Day 3 - Siena
Day 4 - Assisi (and maybe Perugia depending on time)
Day 5 - Montepulciano (with San Q or Pienza as a possibility)

Just makes me wish we had several many more days (or months) to spend visiting hill towns..

I am in Italy right now. When I planned this trip my schedule was so full and everything changed coming here. I agree Assisi is the most beautiful place in the world. We only stayed there 1 day 1 night but will be returning soon for another longer stay. You will find you cant drive into any of the cities inside, have to park outside and do lots and I mean lots of walking. In Assisi alone we followed Rick Steves suggestion and parked at the parking lot but walked very long to the Basilica. We actually took a bus back to the parking lot. Siena you can park by the football stadium and have yet again a long walk but its nice. We actually stayed 30 km away from there in a lovely B&B and we loved it so much we stayed 3 nights versus 2. I must admit we did not see much but since I will be back end of August its ok. The crowds are still not so bad but I imagine it will get worse. I fell in love with Italy and love everything except eating at 8pm...but restaurants just don't open up until then.