From Florence and back to Florence: Discovery Tuscany in 5 days with car


New member
Hi everyone,

I know there are lots of info here and the choices are made based on one's tastes. But just want to ask for your advices on the following. I'll be coming to Florence tomorrow (15 July) and back to Florence on 20 July, I'll be renting a car at Florence and immediately heading to Tuscany (I mean country-side places, I almost don't visit Florence this time) so will need you to help with:

1. Start from Florence (Santa Maria Novella train station, to be specific), what should be the closest Tuscany place to start with? ( I love Chianti region and not sure Montepulciano and the Val d'Orcia are in that direction or not)
2. Any ZTL awareness for all the way from Florence to those Tuscany places? (I prefer countryside roads, not high-way)
3. With the taste of countryside hilltop hometowns and wine farm, what are the best or must-see places that I can do in 5 days by car?
4. Can I look for accommodations along the way? (stop and ask for accomodations for 2 people on the place I'll visit that day)

Thank you very much for any advice


Well-known member
Getting out of Florence


When you pick up the car have them show you the map - as long as you are on your way OUT of the city you really shouldn't hit too many ZTL to worry about. You will probably want to head over towards the Chiantigiana (222) and start winding your way through Chianti.

Most agriturismos don't consider walkings for less than 3 - 4 days...especially in high season ... but you should be OK for hotels and the B&B's. You can check out this link for even more selection:

Hotels in Chianti

Montepulciano and Val d'Orcia are after Chianti (Siena, Monteriggioni and San Gimignano) and definitely merit a day or two all on their own. Click here are a few itinerary suggestions

As for a wine stop, one of my favorites in Chianti, it is located outside of Giaole in Chianti - so it is a mid point between Florence & Siena and not only is the environment beautiful but they are generous with their tastings. I always take my family and friends here because it is warm and welcoming and I feel like it is a lovely representation of Tuscany.

Buon Viaggio


New member
02 more questions

Thanks Donna for your quick reply.

So actually I'll be experiencing Chianti parts (Castellina, Radda..) before going to Siena (Montepulciano and Val d'Orcia) and the roadname should be the Chiantigiana Road (SR222).

Can you or anyone suggest for any offline map/apps with GPS feature so that I can use with my mobile when I'm lost? (I may not have the GPS device in car)

The last question, since I'm not interesting in museums, churchs and I'm into farms, hills and the likes so any other suggestion on the places?

I'll be in touch with this topic along the way.

Thanks again.


The Tuscan Expert ;-)
Staff member
My main recommendation is to look at the accommodation AHEAD of time and contact them.

It is high season, it is a busy time... and you don't want to spend too much of your time going around looking for a place to sleep and being turned away because there is no availability.

Plus there are no signs indicating "vacancy" - you have to turn down roads and get to each place in the countryside to stop and ask - or go online and do it that way, or call.

Go on our main page here:
See that box on the top left column? it has hotels that have last minute availability so that you can book ahead of time. I would set a destination for each night and take each day to explore each area well as you move around.

Some ideas in how to divide the 5 days:
1. Chianti - stay anywhere between Castellina, San Donato, Radda, Panzano
2. San Gimignano and Volterra - stay in Volterra
3. Siena - stay in Siena
4. Val d'Orcia - Montalcino, San Quirico, Pienza, end up in Montepulciano
5. Cortona and Arezzo - end up in Arezzo