Montalcino and Southern Tuscany

I first saw Montalcino from the seat of a bike grinding up the switchbacks from the valley below, on the road from Buonconvento.  I don’t know about the rest of our group but I was sweating and dying.  But when we got to the town and sat in a little park or open space along the edge of the centro storico, looking out over the valley, it was worth the grind.  [You can read more about this trip in my Flying Solo post.] Unfortunately the trip was in 2000 before Shutterfly existed or before I knew it existed and all the pictures are in a physical album not online. I’m slowly scanning them into my computer, though, and here’s the view of the road and valley when we got to the top.

Fortunately I’ve been back three times in the last 7 years and each time it’s been as beautiful as I remember from that first trip.  Two of those times I’ve driven which I’ve written about in my Finding Italy  post.  Suffice it to say it’s challenging to find your way through the roundabouts and into the centro, then back to the parking area.  But it’s extra challenging when you’re driving for the first time (2010) and coming from Rome.  Even with maps and good directions from the owner of the B&B, Palazzina Cesira, I had to abandon the car,  and walk to a gelato shop where I got directions to the B&B.  I’ve written about Palazzina Cesira in my post on Where to Stay and one of the reasons is that Roberto, who owns it with his wife, is a terrific host and was still waiting up for us at 10:00 pm and helped us get settled and get our car to the parking area outside the centro.

Montalcino car park

The photo at the left was taken looking down the main street of the centro.  Our B&B was diagonally across from the enoteca. Talk about a great location!

We came back in 2014, first with my niece and her friends and then with my daughter.

Fortunately we (my sister, daughter and niece) have taken great pictures from those trips which you can see in the gallery below.

On our most recent trip in September 2016 our walking tour stopped here for about an hour, just long enough to have lunch at La Taverna di  Baietto.

Lunch in Montalcino

While Montalcino does a fairly heavy tourist trade, it still seems like a real town.  You can walk out of a restaurant at 10:00 pm and families will be sitting outside their homes watching the kids play or eating a gelato.  People have always been friendly or at least pleasant and I’ve never felt nervous walking around late at night. There are lots of good restaurants (although we never stray from il Grappolo Blu for dinner and La Taverna di Baietto for lunch or afternoon snacks) and many good enotecas.   Our B&B owner, Roberto, recommended the one diagonally across the street from the B&B, Enoteca di Piazza, which I’ve written about in my    Vineyards, wineries and enotecas post.

Other towns of Southern Tuscany

Before I write about Pienza and other towns of southern Tuscany I want to ‘set the scene’ by giving a brief description of my introduction to this area.

On my second bike trip we rode from Montalcino, stopping at Sant’Antimo (see Cathedrals and Abbeys post) then on through Castelnuovo dell ‘Abate up a long series of switch backs to Castiglione d’Orcia.  We stopped in that area to see the Rocca di Tentennano (also spelled Tintinnano), where I think the picture to the left was taken, then had lunch near Castiglione d’Orcia.

In any event from there we rode to Bagno Vignoni, stopping for a while to see it’s unique piazza after which we went swimming at a pool fed by hot springs, looking like total goof balls wearing shower caps from the hotel.  Then we finished the day at Hotel Casanova, where we stayed 2 or 3 nights doing loops out to Pienza and San Quirico d’Orcia.

We stopped one day and had lunch at a lovely vineyard between the villages of Castelmuzio and Montisi, where we did a tour of the olive oil mill and had a degustazione. We also stopped at a monastery, Santa Anna in Camprena, which was the site for the movie, The English Patient.

lunch in a vineyard
a break near a monastery


vineyard near Pienza


I wrote in my journal from that first trip to this area that ‘we rode to Pienza which is a beautiful town with, of course, a grueling uphill the last 5-6 kms.’  We had lunch there and strolled around taking photos.  I ended up walking by myself for a while and remember the lovely little piazzas tucked away in corners of the centro and all the flowers in the windows.

courtyard in Pienza

When my sister and I came back in 2010, I was trying to follow our route from the bike trip and as I wrote in that journal we kept ending up on the road to the Banfi Winery and I almost took us over a cliff.

After that heart stopping experience, I went back to Montalcino and took the main road from there to Pienza.  Parking was a bit of a challenge but there’s a public parking area a few blocks from the centro and we finally found a space.

We took several pictures of the homes as we walked to the centro and here’s one of my favorites.

I wrote in my 2010 journal that ‘We spent a lovely two hours shopping and taking pictures, even getting a couple of free posters.’

As Roberto said, it is the perfect Renaissance town, built mainly between 1459 and 1462, designed by Bernardo Rossellino and commissioned by Pope Pius II.  The main buildings of the redesigned town, the Duomo, Palazzo Communale and Palazzo Piccolomini, surround Piazza Pio II.  In the gallery below, you can see the Duomo and portions of Palazzo Piccolomini, along with part of the wall and a typical street.


We came back with my daughter in 2014, parking in the same spot, then walking through the town taking pictures and having a gelato.  One of our favorite spots from the previous trips, is the walk along the wall where we took lots of pictures.

We stopped in Pienza briefly on our 2016 walking tour.  One of my main complaints of the tour is that they didn’t give us enough time in any town to see or do much.  Plus this time my sister and I weren’t really getting along so after a gelato we sat in the main piazza shown to the left and watched them try to organize a race which was fairly humorous.

San Quirico d’Orcia

Hotel Casanova where we stayed on my second bike trip to Italy was just outside San Quirico d’Orcia and some of us walked there our first afternoon at the hotel. I remember thinking that it was nice to be in a real town that at that time wasn’t touristy.  We stopped at a little café, getting wine and snacks and sat outside on the square, feeling just like natives.

I brought my sister here in 2010, as I wrote above,  more by accident than design.  Unfortunately we arrived just in time for the midday closure of all the shops but we still enjoyed strolling around the town taking pictures.  My sister had the same reaction as I’d had sitting in the piazza, that it felt like a real town.

We stumbled on to a lovely garden and spent quite a bit of time there.  I saw a sign in the garden that said ‘Il Giardino delle Rose.’  Later I looked in a guidebook (Frommer’s 2000) which said it is called Horti Leonini and is a “Renaissance Italianate’ garden.  I just remember it being a delightful respite from the midday heat.


Bagno Vignoni

I don’t recall much about our stop in Bagno Vignoni on my second Italy bike trip; probably because I was exhausted from all the hills in that area.  But I remembered enough to want to bring my sister here in 2010. We spent a fair amount of time wandering the town and ‘both bought some nice gifts at a lovely jewelry and ceramic shop.’

We didn’t have time to bring my daughter to Bagno Vignoni in 2014 which I regret but at the end of our 2016 walking tour, our guide decided to stop here on the way to Rome.  As usual we weren’t given much time, just enough for a much needed cappuccino and for my sister to get some beautiful pictures.

Clearly we found the Piazza delle Sorgenti with its pool a lovely spot since we took almost identical pictures in 2010 and 2016.  Still it’s nice to know that some beautiful things don’t change.


Most travel books give Buonconvento just a few lines and I can’t add a lot myself.  We rode through Buonconvento on my second bike trip on our way to Abbazia di Monte Olivetto Maggiore (see Cathedrals and Abbeys post) and also on our way to Montalcino.

riding through Buonconvento

So when my niece asked if there was a place we could stop as we drove from our hotel in Chianti to Montalcino and have a real Italian coffee, I suggested Buonconvento.  Our hotel’s directions to Montalcino weren’t good and I had to stop at a gas station after several wrong turns south of Siena but we finally got on the right road and found the parking for Buonconvento.

We strolled through  streets that seemed like they had changed very little from medieval times, taking lots of pictures.

Then we stopped for coffee at a little bar seen in the photo below, trying to pretend we were locals.

While I love staying in Montalcino, I think it would be worth it to stay out in the countryside in order to have more time in these small towns.  I remember Hotel Casanova being beautiful, as well as having a nice pool and restaurant.  In 2014 when I stayed a couple of nights at an odd little B&B in Florence, a couple also staying there talked a lot about a B&B they had stayed at in this area.  They couldn’t say enough good things about it and I wish I’d written down the name.

2022 update: In October 2021 I revisted these lovely towns plus spent a week in Montepulciano.  Read more in my Five Days in Southern Tuscany  and  A Week in Montepulciano  posts.


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