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San Gimignano OR Pienza

We’re planning a trip to the Tuscany region for 4–5 days. Our 1st base will be Siena, where we’ll stay for three days & explore Florence and the Chianti region.
We’re unsure about our 2nd base and whether we should visit San Gimignano/Volterra or Montepulciano/Pienza.
Both my husband and I love scenic landscapes, greenery, vineyards, and lakes, but we’re not particularly interested in museums. Any recommendations would be greatly appreciated!

Posted by
357 posts

Will you have a car? Without a car, I think It would hard to visit other towns during a short stay.

San Gimignano is the only town of the four we've visited (over 10 years ago). We spent 2 nights and loved it. The town is small and walled in. It was overrun with tourists during the day and was a nice Tuscan town in the evening. We didn't have a car. No cars are allowed in the town. We hiked outside the town during the day and avoided most of the congestion. It was most memorable for us because we stayed there for the World Cup final game between Italy and France.

Posted by
16565 posts

As Leonard said (who apparently was in San Gimignano on July 9 2006), having a car is sort of a must to base yourself in any town outside of Siena.

Siena is the transportation hub for its province, so you could take a bus to San Gimignano, to Colle VE, to Monteriggioni, and other places nearby. Montepulciano and Pienza are farther south and it takes longer to reach by bus. If you have a car, the Val d’Orcia (Montepulciano, Pienza, San Quirico) is a good place to have a base.

Posted by
14 posts

Hi Roberto,
Thank you for your reply.
Yes we will have a car.
Do you think we are staying less in Siena and 3 days are less to explore Florence and Chinati region?

What do you suggest, which city/town in the Val d’Orcia region would be an ideal base? We would like few restaurants, shop and grocery story to walk down in the evening.

Posted by
16565 posts

Pienza, Montepulciano or any town in the area will work for the Val D’Orcia. You have a car so you can move around, but Montepulciano and Pienza are larger and more visited, therefore they have more restaurants and shops to explore.

Siena can be visited in a day or less. Florence needs at least 3 days to see the basics. Chianti is a pretty drive but there isn’t much to do other than enjoying the landscape and hitting some wineries. Unless you like playing golf (the Ugolino golf course is one of the oldest and prettiest in Italy). You can visit Chianti in a day or even half a day.

Posted by
14 posts

Thank you so much Roberto for your insights.

You just made my husband super happy by sharing the golf plan.