Orvieto, Assisi, Tuscan Region

I have 3 questions:

1. If you arrive in Assisi in the afternoon, and leave the next day for Montepulciano, when do you visit Assisi and why would you travel all that way to spend the night ?
2. Day 27 you are taking a train to the Cinque Terre villages but you leave the next day for Venice. When will you visit the 5 Cinque Terre villages ??
3. If you bus or taxi to Montepulicano on Day 22, when do you do the wine tour ? That night ?

Have you considered simplifying your itinerary. 1 day per stop really doesn't allow you to properly see this great region. Florence is especially worthy of 3-4 days' time.

Tuscany is one of those places that trains don't go everywhere and buses are not always convenient. We especially prefer to stay in an agriturismo when in this region--doing day trips.
I'd suggest you pickup a rental car at Hertz in Orvieto as you leave time and head north. I'd save Florence as the last town and a place to turn the car in. Then take a fast train into Venice (150 mi.)

Carla,
Thank you.
1) Per the drive time, it looks under 2 hours. We would do Assisi that afternoon and next morning.
I am considering removing this stop. We have decided to rent a car as well. I am not sure how the driving conditions are in the area as well?
2) We are taking the high speed early morning train. (Approx just over 2 hours, and we can rest on the ride.)
We would hike it for the day and then return mid afternoon, stopping to see Pisa before heading back to Florence. We will stay in a hotel that is close to the train station so we can leave for Venice on the high speed train the next morning. We will stay in the heart of Florence the 3 days we plan to explore it.
3) Yes, I am debating on doing our own wine tour, hiring a guide, or simplifying it to just one vineyard.

We are wanting to see as much as possible yet have a few days of rest too. Thanks!

David, Thank you. I have looked into renting a car, and you are correct. That is our best option. I assumed driving in Siena would be more difficult, so we were going to drop the car off there. Would it be better to travel through with it to Florence instead of taking the train to each city? I think Assasi might be the city to leave off, so we can spend more time in the Tuscan Region.

I wish we had more time in Italy (12 days), as a year would not even cover everything we want to do.

I am removing Assali. We will take the train to Orvieto and rent a car there from Hertz as suggested. From there we will drive to Montepulciano and stay 2 nights. We will do the wine tour the second day. Do you suggest day trips to Siena? I was thinking we could drive the car to Siena and return it. Then we would stay in Siena and take the bus to Florence. Or would a taxi be better so we can stop? Will we be missing a good portion of the Tuscan Region by doing the trip by bus instead of car? I do not want to drive into Florence. Thanks!

Well, this is interseting. It seems like you are scattered all over the country side. So, here is my 2 cents.

Get to Orvieto and rent a car after you have spent your day(s)? in Orvieto. Drive anywhere you like from there. You can easily drive to Montepulciano, Assisi, Siena, San Gimignano, Volterra, Montalcino, Pienza, or Monteriggioni in the time you have. You will be in the Tuscan wine country, why take time for a Chianti wine tour? You will have just done a big wine tour in the towns you are seeing. Further, the Tuscan towns on the west side of the A1 you can easily drive to the Chianti country if you want to see it. Places like Panzano for example. Have a bottle of wine with lunch. Driving in rural Italy is really fun and no big deal. Avoid the cities however, and turn the car in in Florence then you are at your last destination. QED

Pick a villa, hotel, agritourismo for say 7 days of trip and day trip most of the things on your list by car, plus you will have a place to relax. In most Agri you will find all kinds of wine provided or for sale.

"have a bottle of wine with lunch."

Not if you're driving anywhere after lunch!