help with Tuscany Itinerary

Posted by mkusters2 on 05/02/18 12:12 PM

We will be traveling to Switzerland and Italy in September, spending roughly 3 weeks in Italy. We were originally planning on taking a train only and hitting the major cities but are now looking at renting a car to visit a few of the Tuscany hill towns. I am looking at staying in Florence for 3 nights with a 1 day side trip to Pisa and Lucca. Then we will take the bus to Siena and spend the day and night there. I thought we could then rent a car the next morning and this is where I need help. I would like to drive around the Chianti area (SR222), stopping in Greve (any other suggestions) and also visit San Gimignano. Is it possible to do both in a day? We would also like to visit the Montepulciano/Pienza/Montalcino area. Would one day be sufficient (or a day and a half)? We would then drive to Assisi, maybe stopping in Cortano on the way. Could both those places be visited in a day? From Assisi, we will drive to Orvieto and Civit di Bagnoregio and spend a day and night there. As this will be a month long trip, I am trying to throw in the Chianti area and Montepulciano area to just get a taste of the hill country. This part of the trip just came about after talking to a friend who is also planning a trip to Italy so I am just trying to figure it out (how many nights I may need to stay around there...) so please any suggestions or input (as to an itinerary, where to stay..) would be greatly appreciated. Thanks!

If we did not rent a car and visit Montepulciano and Chianti (SR222), would I get enough of the flavor of that area by just visiting San Gimignano, Assisi and Orvieto (Doing it all by train) or would you highly recommend renting a car and driving the area?

Posted by Stephen

Charleston, SC, USA

05/02/18 01:58 PM

927 posts

We spent 5 nights/4 days last October near Siena and had a rental car. We picked up the car in Florence and dropped it off in Milan at the end of the trip. We visited Cortona and Assisi in one day and had some great scenery and small town stops along the way. We also visited Volterra and San Gimignano in one day with more scenic driving/stops. Finally, we went on a drive where we ended up stopping in Montalcino for a few hours to wander around. In the RS Florence and Tuscany guide book, there are three driving routes that will include almost everything on your list. The drives themselves are not very long but you will stop often and say "wow!"! A couple of the smaller towns we particularly liked were Buonconvento and Montechiello (had lunch in both).

Posted by mkusters2 OP

05/11/18 07:34 PM

57 posts

Thank you so much for your input. It has helped me realize that a couple of these places can be visited in a day and that the time allotted is doable and to put somewhat of an itinerary together. I have obtained the R.S. Florence/Tuscany book and viewed the drives, planning on doing the Heart of Tuscany and parts of the other two.

I have some ideas and questions if anyone else cares to comment. This is what I thought my itinerary would look like with a couple of questions/suggestions from others.

Day 1 -Take bus from Florence to Siena and spend the day and night in Siena.

Day 2 - Rent a car and drive the SS222 to Greve with maybe another stop or two (Castellina, Radda?) along the way. We would not do any wine tours but probably a couple of tastings along the way. After driving the the SS222, I thought we would head over to San Gimignano. I was hoping to take in both San Gimignano and Volterra on that day, staying over night in Volterra, but am not sure if that would be too much in one day. My other thought is do the SS222 drive and San Gimignano, leaving Volterra for the next morning.

Day 3 - Leave Volterra, and drive through part of the Crete Senesi area on the SS438 and SS451 on our way to Montepulciano, making some stops along the way, including Montalcino. Spend the next 2 nights in Montelpuciano.

Day 4- Do the Heart of Tuscany drive with stops and anything else we may have time for.

Day 5 - Head to Assisi, stopping in Cortona on the way. Stay overnight in Assisi.

Day 6 - Head to Orvieto and Civit di Bagnoreggio. Stay in Orvieto overnight.

Does this itinerary seem like a sensible route to take? And my biggest question is what to do with day two, the SS222 drive, San Gimignano and Volterra.

Another thought I had was to rent the car in Florence and drive the SS222, with a couple of stops on the way to Siena but wasn't sure how much time that would take and then how much time that day I would have to spend in Siena. Also wasn't sure about parking the car outside of Siena.

Any comments/suggestions would be greatly appreciated.

Posted by hubestur

Kenmore, WA

05/11/18 08:52 PM

194 posts

We just did much of that route last month. We left Florence late on a Saturday morning, driving to Montepulciano. It was a nice drive, but do know that SR222 is a pretty windy road. With our stop in Greve for the Saturday market, then Siena for lunch and bit of walking around, it took the better part of that day. I was a bit stressed driving into Siena, as I really didn't want to accidentally stumble across a ZTL. We ended up parking safely outside the walls, and it was fine. We needed to be to Montepulciano around 5:00 that afternoon to meet our host, where we stayed for 5 nights.

Your idea of taking a bus from Florence to Siena could work, picking up a car from there for the rest of your trip. You'd be sort of "going the wrong way" from Siena to San Gimignano and Voltera, assuming the rest of your itinerary lies to the south, but if you want to see both those towns and the Chianti Road, not sure there's a better way. We had the same quandary, and decided to skip the western-most towns and save them for another trip.

You'll love Montepulciano itself, and it's a good base for forays out to other nearby towns like Cortona, Pienza and Montalcino, assuming you don't already hit those on your travels. The only other suggestion would be to not move to a new town each night, but select one town as your base. Something about waking up and going to bed in the same place for a few days sort of gives you a sense of what life is really like in one of those small towns.