Updated Itinerary in Tuscany - need advice please

Hello again,

I would like some advice whether my updated plan is ok? My mom did not want to drive a night and back and forth to Prato so we cancelled our B&B and booked separate ones along the way to help.

Day 1: Arrive in Florence around 4pm. Pick up rental car. Drive to B&B. Either stay at B&B for dinner or dinner/explore Greve. (which is a 7 min drive South)

Day 2: Chianti-Scenic drive via route SR 222. Winery visit (haven't booked yet) and lunch.
1. Greve In Chianti (not sure to do first or last so my mom can drink before heading back to B&B?)
2. Montefioralle
3. Panzano In Chianti
4. Radda In Chianti
5. Castellina In Chianti
Optional: Take the route past Monteriggioni to Colle Val d'Elsa then back to B&B and/or Greve OR straight from Castellina to Greve to explore and for dinner then 7 min to B&B.

Day 3: Check out of B&B in Greve and staying one night in Montalcino.
1. San Gimignano
2. Colle Val D'elsa (or do in on the chianti day 1?)
3. Monteriggioni
4. Siena
5. Montalcino (check in to hotel and dinner in town)

Day 4: check out of Montalcino and staying one night in Montepulciano
1. Montalcino (visit town if didn't have time yesterday)
2. San Quirico d’Orcia
3. Bagno Vignoni
4. Pienza
5. Montichello
6. Montepulciano (dinner and drinks here and check in to hotel)

Day 5: Montepulciano and staying one night in Florence.
1. If didn't have time to explore Montepulciano yesterday do in the morning after breakfast
2. Then take A1 back to Florence.
OR should we see other towns nearby before going back?
3. Check in to hotel in Florence and dinner

Any advice if I can/should add/take away any stops or rearrange the order.

Thank you again,


Well-known member
Itin Change

Buongiorno -

as beautiful as Prato is and the surrounding area, this program you have created will definitely leave you perhaps a bit more relaxed on the road. I know it means doing your bags and moving every night but if you guys are good with that then I think you have put together a very do-able and panoramic itin.

Personally I prefer Giaole to Castellina - perhpas because one of my favoirte wineries is located nearby. It is just outside of Giaole in Chianti - the environment beautiful but they are generous with their tastings. I always take my family and friends here because I love the scenery and the "cantina". http://roccadicastagnoli.com/sito/frontend/2eng/wineshop_design.php

Another vineyard that I have visited often (a bit more commercial but still very nice) is between Buonconvento and Montalcino: http://www.altesino.it/ita/azienda.php"]Altesino

If you have time before checking into Florence I suggest you have a stop in Arezzo and really enjoy the small/medium town atmosphere. It is right along the way on the A1, midway between Montepulciano & Florence.

Buon Viaggio,

Donna Denise


The Tuscan Expert ;-)
Staff member
The itinerary looks good, although remember to remain flexible and not move around too quickly just to "see" things.

Day 1 - do dinner and Greve this first night. I recommend the Enoteca Falorni, which is a great place to do wine tastings of many labels with your dinner.

Day 2 - you'll have seen most of Greve the night before, so you can decide whether to head back to have dinner here again and relax or even have dinner out in Castellina or Gaiole, then drive back.

Day 3 - I'd skip Colle just so that you have give SG all morning (do see the Duomo and the tower next door - it has a museum as well) and then spend all afternoon in Siena (the Duomo is a must! and so is palazzo pubblico, at the very minimum).

Day 4 - another busy day! Sounds doable without being in too great of a hurry. If you want to spend time "in" the springs at Bagno Vignoni, do bring flip flops and a towel to at least put your feet in along the stream that runs behind the town toward the cliff as the spring heads down - a full bath might not be advisable, as you do end up being a bit stinky with the sulphur and you still have more places to see for the day after ;-).

Day 5 - as Donna suggested, on your way to Florence stop in Arezzo.
Thank you to you both again for such great advice! :) I will cut it down a bit on the stops.

I am sure we wont see everything but just to have it on my list in case we do have time.

Do you think when we check out of our B&B in Greve we should skip San Gimignano and/or Siena and just go to Montalcino and that area so that we have two full days to explore the Val d'Orcia area?


The Tuscan Expert ;-)
Staff member
I really like both SG and Siena so I would never say to skip them :D

What you could do maybe is on the last day, instead of taking the A1 from Montepulciano back, just spend more time in the Val d'Orcia so maybe take some things from the day before and see them on that last day as you make your way back to Florence.