We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Help with Itinerary for Tuscany hill towns

Racine, Wisconsin
Level Contributor
39 posts
1 review
Save Topic
Help with Itinerary for Tuscany hill towns

After spending three nights in Florence, with a side trip one day to Pisa and Lucca, we would like to rent a car and spend some time in the Tuscany hill towns. I have some ideas and questions if anyone 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. Read someones car was broken into, which I know can happen anywhere.

Any comments/suggestions would be greatly appreciated.

4 replies to this topic
CA
Level Contributor
10,944 posts
3 reviews
Save Reply
1. Re: Help with Itinerary for Tuscany hill towns

There two issues having to do with stops and stops along the way. The first has to do with ZTLs in practically every town; second, the inadvisability of leaving anything of value in a car when parked.

Level Contributor
385 posts
32 reviews
Save Reply
2. Re: Help with Itinerary for Tuscany hill towns

Francophool gives good advice. I have done lots of day trips and left my car unattended but without valuables in without incident. You are taking risk if you leave your luggage or other valuables.

I would stay in San Gimignano rather than Volterrra. Volterra kind of throws you out west. But it would be ok, it is a wonderful town, especially at night.

Going east to Chianti consider going to Panzano, cute town with a crazy butcher, Dario Cecchini

Take a look at Pienza too, as you head south. Nice lunch spot in Tuscany.

Racine, Wisconsin
Level Contributor
39 posts
1 review
Save Reply
3. Re: Help with Itinerary for Tuscany hill towns

Thank you both for the information. I am aware of the ZTLs. Are they fairly obvious/well marked so as not to go into those zones? Also with traveling with luggage in the car, I originally thought we would put our luggage in the trunk when we left Siena to drive the SS222, making a couple of stops along that route and as well as San Gimignano. So with luggage in the trunk, not being visible and daylight, is it still not a good idea to travel during the day with luggage? I was thinking that more of the break ins would happen during the night.

I will have to add Panzano to my list of possible stops. Could either of you comment about Day 2 and if it is possible to do all I have listed. Just trying to figure out where I may end up in order to make reservations. Or maybe trying to make a decision about a home base for 2 nights as not to travel with luggage. Thank you.

Eagle River, Alaska
Level Contributor
798 posts
25 reviews
Save Reply
4. Re: Help with Itinerary for Tuscany hill towns

Not sure if this makes a difference but 18 trips with renting cars and we have yet to see one with a "trunk" - they are all hatch back so much more accessible for a break in. This itinerary seems awfully rushed and "on the go" to me. You are going to bus to Siena and not even have one full day there. You want to "do" Cortona and Assisi in one day. The rest just makes my head spin.

Reply to: Help with Itinerary for Tuscany hill towns
Get notified by e-mail when a reply is posted