Where to spend a month in tuscany


New member
My husband and I are planning to stay in Tuscany for the month of October. He will be working for part of the day, and I will have the days free to myself. We both speak Italian and are of Italian heritage. We are looking for suggestions of where we might rent a place. We are looking for a small city, or larger village. We want to be able to feel like we can be a part of where we are, getting to know the local merchants and feel like we are not vacationers. At the same time, I do want shops and boutiques and things to do during the day, so don’t want a super small village where we might get bored. Any suggestions? We were thinking about Arezzo or Cortona (if that hasn’t become too touristy). Many thanks in advance.
Arezzo would be perfect, while Cortona has become too touristy in my opinion since Frances Mayes and Under the Tuscan Sun came out.

Other possibilities are to choose towns along the train lines, including towns closer to Florence. I would suggest Pontassieve for a small town that would give you all the services and definitely not touristy experience, otherwise Empoli or Montelupo Fiorentino or even Prato or Pistoia. That would also make it easy for you both to take day trips without needing a car. Even Pisa or Lucca would be great in October - as long as you don't stay right in the center, I think you'd still get the local experience if you choose a place just outside the center but walking distance to all that the town offers, including shops and restaurants. I also really like Livorno, which is off most everyone's radar and you can get a really local experience. That would give you the experience of a seaside town in the "off" season since it's October.
Thank you so much for that information. It is super helpful!! We are sort of zeroing in on Arezzo, just want to make sure it’s not too big for us to really get to know and settle in/meet people.
No, Arezzo is not small but the town itself has the feeling of a small town. If you stay central you'll get to visit local shops and coffee shops, after a few days they will recognize you and treat you as a local and not as a passing tourist.
My husband and I are planning a 6-week trip that would cover Tuscany and perhaps 10 days in Emilia Romagna region from mid April to end of May 2023. We would like to use several places as bases to explore from, and use as much public transportation as possible. We prefer smaller villages with some night activities, cafe, restaurants, pastry shops etc...
We will likely fly in and out from Rome from Montreal.
1. We will spend a couple of days in Rome to get over the jet leg and to get a feel of Rome for our next trip. From there, we will head to our first stop ( 2 weeks) to cover Southern Tuscany. Question: 1) Orvieto or Siena as base, or another small village? Is Orvieto too south to reach some of the smaller villages for day trips? 2) This is the stop we will rent a car. Do we need to rent in Rome or can we rent in Orvieto or Siena? Ideally we would prefer to rent in Orvieto/Siena.

2. Next stop is train from Orvieto to Florence for 7 days. We would like to stay in center town for ease of visiting museums etc.. but understand Florence is hectic and expensive for hotels. Any suggestions? Maybe Empoli or somewhere outside Florence on the train line?

3. From Florence take the train to Bologna to explore the region for 10 days. I know it is outside your region of responsibilities, but any suggestion would be much appreciated.

4. Next stop is Northwest Tuscany, taking train from Bologna to Pisa/Lucca for 7 days to explore the region. Or would you recommend another place as base? If we use Siena as base on our first stop, is it feasible to cover this region from Siena as well? Another option is to extend the stay in Florence and do day trips to cover the region. Is it feasible? The train service from Florence to the west seems decent (under $1.5 hours one way) I would love to reduce the number of stops.

5. Train ride back to Rome to fly out.

Somewhere among the itinerary, I would love to fit in a few day in Cinque Terre, but not sure where is good place to jump from? Seems like a 3 hour train ride no matter where you come from (except La Spezia). Is it worthwhile to stay overnight in one of the villages to enjoy the peacefulness at night and the restaurant?

Overall, is it better to work our way from south to the north, or the other way around? My concern is in May, Florence may get quite busy, especially museums? Smaller villages in the south may not be quite as busy. If that's the case , I can reverse the order. But weather wise, it is better to start from the south.

Thank you so much Lourdes.
Ciao Sophie, welcome to our forum!

6 weeks in Italy sounds magnificent! How much have you already "fixed" so far that cannot be changed? You already have a very good outline of what you want to do, so I'll try to go down your questions and offer thoughts on what you already have to help you out in making more concrete decisions on how to organize your time.

--> A few days in Rome at the beginning sounds perfect, I would say 3 days is a good amount to also give you a chance to see most of the main sights and get over the jet-lag. You might also add in the last night out before your flight to spend it in Rome, depending on the time you have your flight to make it easier to get there on time.

Ok so it seems you're planning on 4 weeks overall in all of Tuscany and, yes, south to north makes sense but considering you make your way back to Rome to fly out, you can most definitely plan on making a "circular" route or at the very least, not overlapping.

I believe you should plan your itinerary based o when you'll have/require having a car and when you don't. A car is most definitely not needed in Florence nor in the main towns, but it is whenever you want to visit the smaller towns and villages.
Also, as far as Emilia Romagna, I've personally explored the bigger towns (which are all very well connected with train service) and not much of the countryside, just because I'm still exploring Tuscany ;). So if you're not particularly interested in small towns in Emilia Romagna, I would suggest not planning to have a car at all for that part of the trip.

If you're planning on spending 2 weeks in southern Tuscany to explore the area from the start, you definitely NEED a car during this part. For that reason, I would recommend not staying in Siena and not heading directly there. So taking a train to Orvieto (or to Chiusi, as another option) makes perfect sense. Do you want to explore Umbria as well?

If you're thinking of exploring Chianti area and San Gimignano, it might make sense to include that while you have the car, so let me suggest this:
a week in southern Tuscany, then moving up for another week in the area between Florence or Siena and from here explore Chianti, Pisa, San Gimignano. Driving from there to the even Lucca is not very far, especially if you stay in the area north of San Gimignano. You can explore Siena while either you're south of Siena or north.

Then giving the car up, returning car in Pisa or Lucca and from here consider only public transportation. Take train to visit Cinque Terre, spending 2 nights there, then only then head back to Florence and then spend your week here. From Florence, head north to Bologna and any of the towns you wish to visit. Return via train south to Rome direct, to end your trip.

This way you have car while you need it, then depend on public transport and you have less overlapping - from Emilia Romagna you would have to do a wide circle to get to CT if you left it till later.

What do you think so far? I can offer more recommendations on places once you figure out if this order works for you! Let me know :D