Tuscany in October 4 days


New member

Amazing website, Thank you for your help!

My Husband and I are coming to Italy and we have allocated 4 days for Tuscany. We are not sure how and where to divide our time. We really want an culture experience in this region. Food, Wine + People.

Our Must Do's are:
- any traditional or wine festivals or outdoor Live Music around this time?
- Wineries ( wanting an Authentic Experience,wanting to be hands on, learn about vineyards) maybe a tour at one? or maybe sleep at one?
- Olive Farm?
- Chianti
- Florence
- Siena
- would like to visit small villages along the way while transporting..

We are also wondering where the best place to stay and getting around with what we want? Should we stay 2 nights in Florence and 2 nights in Chianti? Should we rent a car to get around?

Any Advice would be great! We will be coming from the Cinque Terre and Leaving to go to Rome,
Grazie Mille!
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Well-known member
4 days in Tuscany


A vineyard in October can be pretty exciting, they are just starting to experiment with the new harvest and there is lots of activity. Check out this link for a small (but quality) selection of accommodations on a vineyard. I know you said you wanted to sleep in small towns...but for two days I would just stay at the vineyard and really appreciate the “ambiance”.

By dividing your time (even four days is not a lot) by two days in the city and 2 in the countryside will give you a taste of the area, the people and of course the food. And if you are curious about what is out there to eat...I suggest you have a look at our article about dining in Florence (believe me when I say we really put our heart and soul into find the best HA HA) http://www.visitflorence.com/eating-and-drinking-in-florence/

Another article you might want to look at for finding great places to eat is this one about Chianti: http://www.chianti.com/food-and-wine/top-places-to-eat-in-chianti.html

Buon Viaggio,
Donna Denise

Pro Loco Sovicille

Well-known member

it is a good idea to rent a car and choose a base for your holiday in Tuscany - somewhere centrally located and than make day tours to the different towns, areas, villages.

You could choose Sovicille and its countryside as a base, it is a very nice, little and quiet village and those could be your day trips:

Day 1: Siena (from Sovicille to Siena there are only 15 kms)
Day 2: Chianti tour (Castellina in Chianti, Radda in Chianti, Gaiole in Chianti) and a stop for a wine-tasting
Day 3: Florence
Day 4: Monteriggioni, San Gimignano and Volterra or a walk in the nature of the Montagnola Senese that has wonderful colours in october.

Have a nice holiday


New member
Tuscany in January for 4 days

Tuscany Experts. I read the feedback you provided for October timeframe for four days. I am curious about an early January timeframe. I know that it's LOW season to visit. However, I will be on taking a family cruise wherein we are stopping in Pisa and Florence. I have been to both cities before. My finance and I would like to add onto our trip once the cruise is completed. We will be coming from Rome and plan to rent a car. We will return to the states from Florence. We will be picking up the car on Jan 15th from Rome and returning via Florence on the the 18th to return to USA on 19th.

We want a cultural experience with the people, food, and wine. Any recommendations you can provide for routing and where to stay and where to go; given the time of the year would be very much appreciated. Is it feasible to stay in one central location in Siena or San Gimiano and fulfill our "cultural experience"? Your input and advise is very much appreciated.

ccc in NYC


The Tuscan Expert ;-)
Staff member

I would highly recommend using either San Gimignano or Siena as your base! January is low season but the city centers across the region remain well and active, while the surrounding countryside and fields are in sleep mode. The views are just as charming and beautiful, just different from spring or summer.

Since you return to Florence to return the car, make sure to spend the last day there, particularly for the rest of the family that might see enough of it on the cruise tour.

As for places to stay, I would recommend the countryside near San Gimignano at Casolare di Libbiano for example -- http://www.tuscanyaccommodation.com/san-gimignano/ -- and see San Gimginano for half a day, then head to Volterra for the rest (or Volterra first, then SG), do a day trip to Siena, another around Chianti to the various hilltowns. The last day in Florence.


New member
Tuscany Countryside and Small Towns in 4 days.

Dear Tuscan experts,

I read the above and I hope you can guide me along as well. My husband and I will be visiting Italy in October, and have allocated 3 days in Florence, and remaining 4 days in the rest of Tuscany. We have been to Florence 10 years ago, but would love to visit all the sights again. I'm planning to make a day trip to Lucca if we are bored in Florence.

We will be travelling in from Cinque Terre via Pisa, to Florence.

We plan to rent a car from Florence and drive out to base ourselves elsewhere in Tuscany for the next 4 days. I read in some forum Chianti is a good base to drive around, so I was thinking to allocate either:

3 days stay Chianti and drive to SG and other places, 1 overnight stay Siena OR

4 days stay Chianti then drive all around Tuscany, to Siena for day trip, SG, Montalcino, Montepulciano and any other small towns if time permits. My plan is to allocate 1 full day in Chianti and another 1 day at other vineyards (likely Montalcino?) around the region.

My concern about driving to Siena for a day trip is whether it is easy to drive back to Chianti at night. We have never driven in Italy before. I read that Siena is beautiful at night, so I hope to get a glimpse of how it looks like in the evening.

I am also considering whether to stay in a vineyard in one of the villages, but I read that these places may not be very assessible, and I have only 4 days in Tuscany (besides Florence), so I hope to see as many places as possible.

I will drive back to Florence to drop the car at the end to travel out to Bologna.

Would love to hear suggestions from you on where to base ourselves and how best to travel around all the lovely areas in Tuscany.
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Well-known member
Vineyards in Tuscany


I suggest that you divide your 4 days: 2 in Chianti and 2 in Siena. There are many lovely B&B’s you can opt to visit that will give you a wonderful point of departure and overview of Chianti. Two of my favorites are located in the small town of San Donato:


But to be honest there are so many from which to choose: http://www.tuscanyaccommodation.com/chianti-bed-and-breakfasts/

As for Siena, Hotel Athena is a great option if you are looking to do a day trip but want the experience of staying in the city for at least one night. But you can check out this link for more options: http://www.tuscanyaccommodation.com/siena-hotels/

Buon Viaggio,
Donna Denise


The Tuscan Expert ;-)
Staff member

I would do more like Donna has suggested, since you want to also go down to Val d'Orcia.... 2 days dedicated to Chianti, with drive to San Gimignano on one day, 2 in Siena, with one being a day trip south toward Montalcino and Montepulciano and a full day in Siena.

Driving at night is not bad, these are country roads but not particularly lit but there are many reflective signs at all curves. You can use high beams if it is particularly late and no other cars are around.

The 2 nights in Siena (we've stayed at Hotel Athena, it's great with a car as they have parking but right inside the walls and close to the sights - not a ZTL area so you can drive in, park and then within 15 min be in Piazza del Duomo) will permit you to enjoy Siena at nighttime, which is lovely!!


The Tuscan Expert ;-)
Staff member
In deleting some spam we have on the forum, I think I accidentally also included Twoverlees yesterday, went meant I banned her and also deleted her posts. I apologize for that, it wasn't meant to happen!

So I'm reposting her initial question on this thread -- then hope to add some replies to her questions, which had yet to be answered (I was working on it)!

From Twoverlees:

My husband and I will be driving from Rome to Tuscany in October. We will be staying outside Siena for 3 nts.
Our first stop will be in Montelpuciano and then on to Montalcino. We are struggling with which wineries to visit! We'd prefer to go to wonderful, small, excellent wineries. Preferably ones that do not distribute in the US as we would like to bring back some different Brunello which we can't get here in the states. I don't mind paying $$$$$ money for Brunello as long as it is excellent as I have a very discriminating wine snob for a son. I am looking to avoid Banfi and other large exporters. Any suggestions?
Also, which wineries would u recommend in Montelpuciano? Or would you just recommend more time in Montalcino enroute to our lodging in Siena.
Torn about which Chianti Classico wineries we should see?
I've worked in the wine industry so I really am not looking for tours as much as beauty, authenticity, good value wines and enjoyable tastings. We don't need to make appts for just tastings do we?
Is there a limit as to how many bottles we can each bring back?
Thanks so much!!!


The Tuscan Expert ;-)
Staff member
Ciao Twoverlees,

I believe that as long as you drive through the Val d'Orcia area, from Montepulciano to Montalcino, in a leisurely fashion you should most definitely enough the beauty and wonderful products that the area offers, wine being only one of it.

Remember if you're driving to be careful - you can't do too many wine tastings and get behind the wheel!

Generally, the enotecas will allow you to sample a wider variety of labels. In Montepulciano, the Enoteca for the Consorzio del Vino Nobile is actually a great place to do wine tastings of ALL of the region's wine producers that belong to the consortium -- one way to sample various wines without having to drive to each and every one on your list. You can buy all of the member's wines there - no appointment needed. It is right in Piazza Grande.

Some more suggestions in the area:
Tenuta Valdipiatta (www.valdipiatta.it)
Podere Le Berne (www.leberne.it)
La Bandita e Lunadoro (www.lunadoro.com).

Let me think on the other ones for Montalcino and Chianti -- I think Donna has a few suggestions for small prodcuers in Chianti near Greve, let's see if she posts.
In the meantime, also check out the ones we recommend on here: