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Siena or Montepulciano/Montacino/Pienza

My question comes on the heels of an earlier question about a day trip from Florence. We're staying an hour north of Rome in a charming hill town for 2 weeks and will have several opportunities for day trips with car. In considering the area between Orvieto and Siena, where would you spend your time? In the larger picturesque, touristy Siena (obviously, poster Kelly wouldn't!) or the smaller perhaps more charming Montepulciano/Montalcino/Pienza and the scenic drives and abbeys around there? (Note: we'll also be seeing Rome, Orvieto, Assisi, Spello, San G, Volterra, CT, Florence, Pisa, Viterbo, Tarquinia, Tivoli, Ostia Antica) I'm a little concerned I'm just trying to hit a bunch of towns just for the sake of seeing them vs. deriving a sense of la dolce vita! Opinions, per piachere!

Posted by
9436 posts

We loved Montalcino, Montepulciano and Pienza and thought they were really charming, relaxing, friendly and very enjoyable to be in and to walk around and explore. And we loved the scenic drive between them. We didn't like Siena at all (gasp!)...we thought it was dark, claustrophobic, not enjoyable, not friendly and not the least bit charming.

Having said that, many people rave about Siena and you might regret not seeing it for yourself since you'll be so close.

We've done two trips to Tuscany, one slow and relaxed - not seeing everything and the other seeing most of the towns and exploring. They were both good trips. You could just wait and decide when you're there how you'd like to spend your time.

Posted by
282 posts

Greetings from across the Columbia River! Strong vote for Montepulciano/Montalcino/Pienza. Wonderful, unique, beautiful towns. I especially loved Pienza, with its gourmet food shops and little museum and garden. If you would like a list of where we ate in the area, just send me a message and I will email it to you.

Posted by
2023 posts

Also not a huge fan of Siena--just not on the same charm level as Montalcino, Montelpulciano, Pienza--we really loved the little town of San Quirico. Did not especially love San Gim but it was good to see it once. If you visit Montalcino you can tie in a visit to S'Antimo Abbey. Have a great trip--you will see lots of Italy!

Posted by
111 posts

It sounds like there are those of us who like the smaller town experience. I really appreciate the feedback on these. We are getting our car in Pisa and driving down to our 2-week location outside Viterbo. I might have to re-think the stop along the way to San G and Volterra. The biggest hassle sometimes is the parking situation. Like Steve said, just pick a couple and enjoy the heck out of them.