Siena and Central tuscany in October

Hi everyone :)

This site is truly great- a wealth of information. My friends and I are visiting some parts of Tuscany next week. We are all very excited to 5 days of relaxation, good food and good wine and lovely scenic views. I;m a very keen amateur photographer and would love to take as many beautiful photos as possible. We have drafted our itinerary and I'd like your advice and tips on this. We have a car and we will be based in Agriturismo La Selva Strada Pian del Lago 19 (Siena).

Itinerary as follows:

Thurs- arrival at Pisa then drive to Siena and have dinner there- taverna San Giuseppe seems to be highly recommended on trip advisor? Any other ideas?

Friday 03/10

Siena to Monteriggioni to Volterra to San Gimignano

Saturday 04-10

Siena to Montepulciano (stop on the way back) to Pienza to Montalcino to Radicofani to La Foce to Montepulciano and back to siena

Reservation at Montalcino poggioantico wine estate

Sunday 05-10

Siena to greve in chianti to panzano in chianti to castellina in chianti to Radda in Chianti to Gaiole in Chianti to Castelnuovo and back to Siena and walk around Siena


Siena to Florence and then back to enjoy Siena some more

What do you think of the above plan? Any recommendations from your part? Any restaurants and definite places to visit?

Mant thanks for your help and keep up the great work L)

Roberta (Malta)


Well-known member
Dear Roberta,
your itinerary is definitely full of places to visit!
I like the day completely dedicated to the Chianti area (the locations you've mentioned are actually the MUST SEE of this zone). I strongly recommend the Antica Macelleria Cecchini for trying a traditional cuisine with local products. Beef meat - the T-bone steak in particular - and CHianti wines are their specialities. It's located in Panzano in Chianti and offers both quick and complete meals.
And I like as well the day dedicated to the Valdorcia, whose most representative locations are Montalcino, Montepulciano and Pienza - if you've time, drop by Castiglione and San Quirico d'Orcia also. Pienza in particular is a little gem, declared a World Heritage Site by Unesco.

I would dedicated a bit more time in visiting Pisa and its Miracle Square - the Leaning Tower is actually something you should see at least once in your life, as well as Siena. You'll probably be a bit tired when you go back to Siena on the evening, after an entire day back and south into Tuscany, so touring Siena on your way back home in the evening won't give you the chance to fully enjoy the city...
And Florence as well: it actually deserves more than just half a day visit, have a look at this 5 days itinerary: you probably won't have time for staying two days in Florence, but a complete day is really necessary:

What do you think? You should sacrifice other locations, like Volterra and Monteriggioni, but Pisa and Siena are worthy this choice according to me! And try to remain a bit flexible once you're here in Tuscany to last minutes changes and for taking your time to just relax and enjoy our beautiful region!