Tuscany - Volterra/San Gimignano or Montepulciano/Montalcino

Yes, rent in La Spezia as the train trip to Florence or Siena from there is tedious and a car allows you to stop and visit along the way. For example, if you decide to stay in Montepulciano or Montalcino, you can visit Volterra during your drive fromLa Spezia to your base,

We favor Montalcino as we love the wine there and the day trip from Montalcino to Pienza and Montepulciano is a lovely day. Not to miss: the abbeys of Sant’Antonio and Monte Olivieto. You can even walk from Montalcino to Sant’Antonio and take a bus back.

Tough call as both are great options. I've enjoyed both for different reasons and don't have a clear favorite.

Volterra/San Gimignano: These are less of a detour in route to Florence. I would stay in Volterra, which has a lot to do and see for a relatively small town, and visit San Gimignano. There's a lot of Etruscan history in Volterra, which I found interesting. It's a true hill town and you'll need to park outside the walls, so expect some uphill walks into the center (some are steep).

Montepulciano/Montalcino: These are obviously further away but in a beautiful area of Tuscany. In addition to the places mentioned above, you could drive to Chiusi for its Etruscan sights. There's more of a wine focus in both towns than you'll find in Volterra/San Gimignano. Montalcino is flatter than Montepulciano and I believe it offers more options for the evening, so I would stay there. Wine tours from Montalcino are also easy.

If you are looking for a base to take day trips to various Tuscan towns I wouldn’t choose Volterra.
Although visiting Volterra is a must, however the town is not ideally located to visit the rest of Tuscany, therefore I would choose somewhere else as a base.

Thank you for all your replies! It seems as though maybe Montepulciano might be a better match. I do love wine :) Although Volterra looks beautiful too.

In my opinion, Montepulciano is the best place hands down. We have travelled to there so many times and it keeps pulling us back. The restaurants are fantastic, there are wonderful shops and galleries lining its streets, and amazing cafes.

Montepulciano is also a great base to also explore uncountable hilltop towns and wineries. Within a short drive, you could even visit Cortona, the setting for "Under the Tuscan Sun" - although much of it was actually filmed in Montepulciano!

Here are a few of our favorite places to help you:

Montepulciano Dining Suggestions:

L'Altro Cantuccio (http://www.laltrocantuccio.it/) – this is an amazing restaurant that puts a modern twist on typical local recipes. Their food is art, but it is not pretentious at all! This is a laid-back place that happens to produce amazing food.

La Grotta (http://www.lagrottamontepulciano.it/intro.php) – this is probably the most elegant restaurant. It’s located at the base of San Biagio, the 500-year-old church at the base of town. While the first two restaurant are more laid back, this is a restaurant you should dress up to eat at. Wonderful food and wonderful service.

Montepulciano Accommodation Suggestions:

Fonte Martino Guest House (https://www.fontemartino.com) – this is a little gem located just outside of town, but close enough that we walked to town. I came across it last year and have stayed twice and will be there again this October. The owners are American and created something really special that is beautiful and full of amenities. They really helped me on suggesting amazing places to see and experience. Based on what you described - watching "Under the Tuscan Sun" - this is probably the place for you! That's one of the reasons I was drawn to it.

Charming Homes Montepulciano (https://www.charminghomemontepulciano.com/en/) – These are charming apartments located in the city walls of Montepulciano. We personally stayed in Alberto57 and it was wonderful. Very clean and perfectly located along the main Corso (main shopping street). Alberto (the host) is a wonderful person as well. There are great little cafes for morning breakfast and Caffe Poliziano, an amazing 150 year old art-deco café, is only a short walk up the corso.

I hope this helps you out - have a great trip!

Be assured that whichever you choose, you’ll have a wonderful time! We stayed in Greve and made day trips to both areas. Volterra and San Gimignano are charming, but as mentioned, not quite as convenient to the heart of Tuscany.

If you stay south, be sure to Time your visit to the Abbey of Monte Oliveto so you can come back in the evening for vespers. It is celebrated in Gregorian chant. We were there mid-December and besides the monks, it was just us and a lady from a nearby village. We were invited to sit with the monks and encouraged to participate in the responses. It was a highlight of our trip.

Thank you so much for your replies and especially the recommendations for accommodations and restaurants! It sounds like we will have a wonderful trip. I'm going to spend some time in the next few months making some reservations. Grazie!