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Tuscany in Sept

Three couples traveling to Siena/Chianti area in September looking for suggestions as to hill towns to visit? We were thinking of 5-6 nights in Chianti area and then end with 2 nights in Florence. Would like to visit some wineries and enjoy a relaxing pace using one hotel as our central point. We welcome your suggestions. Thank you.

Posted by
11651 posts

Panzano, Castellina, Greve and Radda are towns you should consider visiting.

Posted by
16185 posts

Besides the Chianti Hills suggested by Suki above (all of those are Chianti villages) the most visited towns between Siena and Florence are:
Siena itself
San Gimignano
Monteriggioni
Colle Val D’Elsa
Volterra (a bit further west from Colle VE)

South of Siena the most visited are:
Montepulciano
Pienza
Monticchiello
Montalcino

East of Siena the most visited are:
Cortona
Lucignano

If you want to take a lot of day trips you will need a rental car (or two rental cars for 6 adults). The best base is in the Monteriggioni/Siena area from which you could visit all of the above towns all within one hour each way.

Posted by
3112 posts

If your visit is during the first half of September and you stay in the Chianti area, there are a couple of nearby wine and food festivals you may enjoy. The annual Chianti Classico festival in Greve is held on the 2nd weekend and there's a food festival in Pontassieve that I enjoyed, usually held on the 1st weekend. The Ruffino winery is in Pontassieve and may offer tours the weekend of the festival (don't miss sampling their Modus wine). Be sure to appoint a designated driver if visiting festivals or wineries by car.

Posted by
11 posts

Thank you all for these excellent suggestions! I appreciate your feedback very much.

Posted by
34 posts

Dear Roberto, Do you have a specific day order of visiting these towns that you listed? Which town would be your choice as must-see? How many hours in each town would you say is a reasonable amount of time for the visit per day? I also will be staying in Tuscany for 6 night. Thanks so much for any additiona advice you can provide with your wonderful list!

Posted by
1175 posts

As for lodging....consider these:

Cretaiole - theisabellaexperience.com. Isabella is the consummate host and has several properties to view.

Borgo Argenina - Elena has a lovely vineyard property, fabulous homemade breakfasts overlooking the vines, and she cooks one night with all of her guests. It makes for a delightful evening !

If you have a larger budget, take a look at lupaia.com.

We have visited Roberto's great list of villages from all of these locations.

Posted by
2 posts

We are arriving in Florence (2-adults) on Friday 9/6 , then flying to Palermo on Sunday am 9/8 to begin our 11 Tour of Sicily. Rather than staying 2 nights in Florence, where we have been before, we were thinking of 2 nights in Sienna. We are looking for nice accommodations, centrally located, that won't break the bank to visit & hang out in Sienna.

  1. Any suggestions on places to stay ?
  2. Are we making a mistake by trying to cram too much in ?

Any feedback would be greatly appreciated.

Pit & Teddy