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Day trip from Siena - looking for advice

We're going to have three nights in Siena at the end of October, after we spend time in Florence. Wondering what you all think about a day trip from Siena? First trip to Italy - looking at Get Your Guide Tours, RS recommends Tours by Roberto - Montepulciano / Pienza? Monteriggioni/ Chianti area? Montalcino? We'd like to see the countryside, hill town area... what would you suggest? Tell us what you've enjoyed. We'll see Siena sights on our own, and will probably want some down time to just wander and soak up Siena.
Thanks for any help!

Posted by
8337 posts

San Gimignano and Volterra would be a good day trip. Certaldo's maybe 5 miles from S/G too.

Posted by
519 posts

We stayed four nights and two of the days we did wine tasting, which we really enjoyed. Arranged with Tuscan Escapes and Tours of Tuscany. Liked the former better, but both were good. Down to Montalcino and Montepulciano. Spent the other full day and partial days exploring Siena.

Posted by
7225 posts

Tours by Roberto gets high marks. He books up early so check to see if even available in Oct

Get Your Guide is a third party reseller, they don’t actually run any tours.
If you scour the GYG listing you can usually find the actual tour company - book directly with them

Look for a tour that takes you thru the Val D’ Orcia- Montepulciano, Pienza, etc those are our favorite towns

Posted by
1682 posts

I don't take tours but all the options provided look good to me. I'd aim for what David suggests.

Using public transportation, about 45 minutes to Certaldo. Stop for a coffee and a walkaround.

From there, about another 45 to San Gimignano. Not sure if you'll have time for Volterrra as well.

Posted by
28 posts

Thank you so much for all your suggestions and information! We'll follow up on your ideas and will certainly enjoy what sounds like a classic area of Italy.

Grazie! S&S