I have been fortunate to visit Montalcino and surrounding towns five times between 2000 and 2021; staying, all but one of those times, for 2-4 days. I’ve divided this post by towns (borghi) and then by years with separate sections on Where to Eat and Where to Stay.

Montalcino

2000 Bike Trip

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 also read more about this trip in my Flying Solo post.]  I’ve scanned in my photos from that trip and while they’re not as good as digital photos, I think the photos below give an accurate feel for the climb to the top.

After resting in the park, we pedaled to our hotel (Hotel dei Capitani) and almost immediately after checking in, our guide said we were riding to Castello Banfi, a winery outside of Montalcino, which is still regarded as one of the best in the area, although the beautiful Castello is no longer used for wine tastings. (See Vineyards, wineries and enotecas post).

After a lovely wine tasting we all put our bikes in the van and returned to Montalcino.  Although this sounds crazy now, I’m fairly certain that after we returned to the hotel and cleaned up, we did a walkabout, then had another wine tasting (with aperitivi) at Enoteca la Fortezza.     

We were on our own for dinner so a couple from New Jersey suggested Il Grappolo Blu, a tiny trattoria on the main street.  We had a  fabulous dinner, staying fairly late while it stormed outside.  (Read more in the Where to eat section below.)

We headed out the next morning pedaling first to Sant’Antimo and then through the towns described in the section on Other Towns of Southern Italy.

2010

Before I write about this trip, I have to talk a bit about getting there when you’re not on a bike.  Like many hill towns in Italy, there’s no train station, so your options are a local bus or driving.  In 2010 when my sister asked me to take her to Italy and visit all the places I’d seen, I put together an itinerary that I would never do again.  We flew from London to Rome, because we were going back through London to Scotland after Italy and I rented a car at the Rome airport, then drove us to Montalcino from there.

 I’ve written about my driving experiences in my Finding Italy  post.  But by the time I got us from the Rome airport to Montalcino, it was 10:00 pm and I had no idea where to go.  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.  (Read more  about Palazzina Cesira below and in my post on Where to Stay)  Luckily our wonderful host, Roberto, was waiting up and helped us unload and then get to the parking area outside the centro. (Hotels in the centro generally provide parking passes for their guests.)

We spent two full days, walking through the town, enjoying the views, enotecas and shops plus drove to Banfi, Sant’Antimo, Bagni Vignoni, San Quirico d’Orcia and Pienza.  Our B&B was in a great location and Roberto gave us excellent recommendations on where to go as well as where to buy wine, Enoteca Di Piazza, which was diagonally across from the B&B. What could be better!

2014

My sister and I came back in 2014, first with my niece and her friends and then with my daughter.  My niece and her friends could only stay from Friday afternoon until Sunday morning so our one excursion was to Castello Banfi, which they loved, and the rest of the time we spent eating, drinking, shopping and buying wine to send home from Enoteca di Piazza. 

The morning when I had to drive my niece and her friends back to Firenze and pick up my daughter, the town seemed to be sitting on a bed of clouds and I think the pictures are unusually pretty.

When my daughter arrived, we had another day and a half in Montalcino and did another wine tasting at Banfi plus drove to Pienza.

2016

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

2021

In 2021 my sister and I drove to Montalcino from San Gimignano through Buonconvento.  We spent 3 ½ days here and went to all our favorite places, Sant’Antimo, Bagno Vignoni and Pienza plus lots of walking around the town despite high winds and chilly temps for the first day and a half.  (Read more in my Five Days in Southern Tuscany  post)

What has kept me coming back is that 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 and many good enotecas.   

Other towns of Southern Tuscany

Villages Between Montalcino and San Quirico

2000 Bike Trip

As mentioned above,  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 in the gallery below 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 its 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.

Bagno Vignoni

2010

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.’

2016

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  to take 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.  Here are a few from our 2021 visit.  It’s nice to know that some beautiful things don’t change.

San Quirico d’Orcia

2000 Bike Trip

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.

2010

I brought my sister here in 2010, more by accident than design, after a crazy drive when I almost took us over a cliff in a tiny hilltop town.  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.

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.

2010

After the heart stopping experience where I almost took us over a cliff trying to find the road that goes to Sant’ Antimo and on to Pienza, 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.

I wrote in my 2010 journal that ‘We spent a lovely two hours shopping and taking pictures, even getting a couple of free posters.’  And for those shopping aficianados, Pienza is known for its great cheese shops.

As Roberto, our host at Palazzina Cesira,  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 above, you can see the Duomo and portions of Palazzo Piccolomini, along with part of the wall and a typical street.

2014

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.  We only had time to sit in the main piazza shown on the left, while eating a gelato and watching them try to organize a race which was fairly humorous.

 

 

 

2021

Our 2021 visit wasn’t as pleasant due to unusually high winds and chilly temperatures but once we reached our favorite area along the wall, we found it was protected from the winds, allowing us to enjoy the beautiful views.

Buonconvento

2000 and 2014

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.

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 thought of 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.

2021

And Buonconvento seemed like a logical stop as we drove from Ulignano to Montalcino in 2021.  We walked around for more than an hour, having a coffee at the same little bar.

 

 

 

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.  As I mention below in the Where to Stay section,  Hotel Casanova is in a beautiful location, with a nice pool and restaurant–and now a wellness center.  

Where to Stay

Hotel Dei Capitani

Homepage

Our bike trip stayed here in 2000 and I thought it was comfortable and enjoyable. 

So when I planned our 2014 trip, I booked it for my niece and her friends since Palazzina Cesira required a minimum 3 night stay.  They complained about their rooms, e.g., one room smelled like smoke but I would still consider it, for the pool and location.

Casanova Hotel (now Wellness Center)

https://www.wellnesscentercasanova.it/it/

 I thought his hotel, located along SP146 between San Quirico d’Orcia and Pienza, was wonderful when our bike group stayed there in 2000; a pool and beautiful terrace, a restaurant and an easy walk to San Quirico.  It has grown exponentially during the intervening years and now has a large and expensive wellness center.  I think I’d have to win the Power Ball to stay there again. 

Palazzina Cesira

We stayed here in 2010 where we had a very modern, albeit small room on the top floor and again in 2014 with my daughter.  Our 3 person room that year was a bit dark but as always, the owners, Roberto, and his wife, went out of their way to be helpful, making breakfasts to order, providing ideas for side trips as well as directions to other towns.

(Read more in my  Where to stay in Italy post, and see more photos.)

 Albergo Giardino

http://www.albergoilgiardino.it/ 

Unfortunately when we planned our 2021 trip to Montalcino, I could no longer find a web site for Palazzina Cesira so we stayed at Albergo Giardino.  I’ve written about it extensively in my     and     posts.   I would definitely return, especially for the opportunity to visit Paradiso Cacuci.  Plus I have to say that it is far easier to reach by car than Palazzina Cesira.

 

Casanova Hotel (now Wellness Center)

https://www.wellnesscentercasanova.it/it/

 I thought his hotel, located along SP146 between San Quirico d’Orcia and Pienza, was wonderful when our bike group stayed there in 2000; a pool and beautiful terrace, a restaurant and an easy walk to San Quirico.  It has grown exponentially during the intervening year and now has a large and expensive wellness center.  I think I’d have to win the Power Ball to stay there again. 

Where to eat and drink 

Il Grappolo Blu

I fell in love with this little trattoria the first time I ate here and returned multiple times with various family members and friends.  The food was great, the service excellent and the drinks generous.  (Read more in my  post)  So I was terribly disappointed  when we returned to Montalcino in 2021 and found that it had changed owners and both the food and service were poor.  See     and     posts.

Taverna di Baietto and Enoteca di Piazza.

https://enotecadipiazza.com/

After the major letdown of finding that il Grappolo Blu was no longer good,  the Enoteca and Taverna became our home away from home in 2021.  In prior years we had stopped here for lunches and wine tastings, but we ate most of our meals at the taverna in 2021.  (As a side note, the enoteca and taverna are basically the same operation.)  You can read more in my Five Days in Southern Tuscany and Vineyards, wineries and enotecas posts.

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