Five Days in Southern Tuscany

San Gimignano, Montalcino and Pienza

It had been five years since my last trip to Southern Tuscany and in 2021 I was anxious to see all my favorite places again.  But it seemed like a case of you can’t go home again, at least with respect to Montalcino and Pienza.  So I’ll start with San Gimignano and Ulignano, where we stayed for about two days.

We had been in Firenze, so we took the train to Siena where we rented a car at a Europcar office about two miles from the train station.  (And I can’t recommend this office or Europcar in general.  The ‘agent’ pressured us to upgrade saying we had reserved a smaller car than I know was the case and also tried to pressure us into buying extra insurance.  When we returned the car, we were significantly overcharged.)

I had mapped out the route from Siena to Ulignano using Google maps and then printed out the maps but the maps were wildly  inaccurate with respect to getting us from near the train station to the Firenze-Siena (Fi-Si) highway so I just went with my instincts and got us to the highway with no problem.  But almost immediately we got caught in a massive traffic jam caused by a combination of construction and an accident.  Once we got through that mess, we continued north to Poggibonsi, took the north exit and followed the signs to San Gimignano and Ulignano.  We came into town on a different road than I had mapped but given how small Ulignano is, that didn’t cause any problems.

San Gimignano and Ulignano

In 2016 my sister, niece and I had a lunch and wine tasting at Tenuta Torciano in Ulignano, just a little northwest of Poggibonsi.  We enjoyed our wine tasting so much (see Vineyards, wineries and enotecas post) that we continued to buy wine from Tenuta Torciano. In 2021 my sister received a coupon from Torciano for a free night at their hotel, Vecchio Asilo.  (See Where to Stay below).  So we decided to use it as a base to return to San Gimignano, one of our favorite towns, (see Siena to St. Gimignano  post).

Wine Tasting at Tenuta Torciano

When we were checking in to the hotel, we told the staff person that we had a coupon for a wine tasting and for what we thought was supposed to be dinner.  (Wine tasting yes, dinner, no)   He called the vineyard and was told that the only time they had available that day was at 4:30 pm.  We agreed to the time then hustled around, unpacked and showered.

After parking at the vineyard we had to go through the whole Cirque du Soleil of trying to talk to the staff through the speaker on the gate.  They finally let us in but it took forever before they  found our reservation. Eventually we were seated outside in the arbor.  Luckily the wind had died down and it was sunny and very pleasant.  We had 4 wines and a dessert wine but just a small plate of meats, cheeses and bruschetta.  So I was completely toasted. But what fun!!  We even had photo ops with the waiter who was trying to chase a rooster that kept trying to join us.

My sister bought three bottles of wine which we enjoyed over the next few days.

A Day in San Gimignano

San Gimignano technically is not southern Tuscany but has a similar vibe.  It was only a short drive from the hotel on SP429 to San Gimignano and I remembered the route around the walls to the parking lots.  It was fairly crowded but we squeezed into a spot and took the elevator up to the edge of the centro.  Since it had been 5 years since our last visit, I took photos from the elevator to the main street so I’d be sure to go back through the right gate.

As we walked into the main piazza, we smiled, seeing places we’d been before, like a little restaurant where we’d sat outside having Moretti Rossa with my daughter.  (see Siena to St. Gimignano  post).

We walked around Piazza del Duomo and up a couple of side streets taking pictures.  Then we walked down to Piazza della Cisterna, taking more photos.  From there we took a fairly steep street almost to the edge of the centro.  There were lots of interesting shops, and we stopped in two that had beautiful ceramics. As we walked back to Piazza della Cisterna we noticed a small walkway along the wall where there were spectacular views over the valley.

We headed back to Piazza del Duomo and wandered around a bit before we could find the ticket office for the tower.  We bought tickets to walk up Torre Rognosa (I think) and made it about 2/3 of the way before the open stairs freaked us out.  We stopped on the way down and went through several rooms of religious art.

We hung out in the piazza for a few until we saw a table outside open up at one of the restaurants.  I ordered a pasta which was excellent and my sister ordered ‘insalata di tonno’ which in Italy is typically fresh greens, tuna, tomatoes, mozzarella and other seasonal vegetables, served with balsamic vinegar and oil.  We lingered over our food enjoying the sun and the people watching.

Afterwards we walked up and down the main street looking for a place to buy some panini,  finally finding a little shop as we walked to the car.

Where to Stay

Hotel Vecchio Asilo

While the hotel is a good location for visiting San Gimignano, we had difficulty finding it initially.  When we turned left at the main intersection, drove all the way to the end of town, then back without seeing it so we stopped at the vineyard and asked for directions.  The staff would only talk to us through the speaker on the front gate but told us to go back to the end of town again.  This time we found it, just before the road makes a major curve.

A staff member helped us bring our cases in and park the car on the narrow gravel lot, then checked us in and as mentioned above made reservations for our wine tasting.  The rooms were spacious and pretty and they serve a very generous breakfast.

The hotel has two nice terraces where we relaxed the next day after returning from San Gimignano.

But there’s no one there after 4:30 or 5:00 pm.  Our second evening, my sister and I couldn’t find anyone in the hotel so we sat in the breakfast room having wine and panini we bought in San Gimignano, because we didn’t see a restaurant anywhere in Ulignano.      Two couples arrived, asking ‘Where are the girls?’  ‘What?’ After asking where to get wine, they went upstairs.  Not long after that a man who had helped with breakfast (and I think is part of the family that owns the hotel), walked in, said hello and went upstairs.  Then the couples came downstairs, made themselves ‘dinner’ in the kitchen while talking to my sister and me then took their food outside.  Weird!!

Buonconvento and Getting There

 In my Montalcino and Southern Tuscany post, I added Buonconvento as a footnote to the more popular towns in southern Tuscany, but I’m going to say a few words about it here, in part because it’s an integral part of getting to Montalcino, if you’re coming from the north, and definitely worth a stop.

Given the huge traffic jam on the Fi-Si, Monday, I looked for an alternate route but ultimately stayed with my original plan, driving us from Ulignano  to  the Firenze Siena highway and then to Monteriggioni where we picked up the SR2.  Miraculously the one lane construction that had traffic snarled on our way to Ulignano ended just before the Monteriggioni exit and the Fi-Si itself was far less backed up than Monday.  Following the SR2 to Siena was both easy and beautiful.  I made a couple of wrong turns in Siena and nothing looked like Google maps.  But I recovered and with a sigh of relief got us past the A1 headed to Buonconvento.

We had one hiccup when my sister said ‘there’s the turn to Buonconvento.’  When it turned out to be a four lane highway, I thought we were on the autostrade but it was just a bypass and the exit to Buonconvento came up quickly.

After a couple of wrong turns, we found parking along the main road going through Buonconvento.  (I didn’t see the place to pay but luckily we didn’t get a ticket.)  It was a beautiful day by then so we walked from the car along a garden wall, to the centro and up and down several streets, taking pictures.  We then had coffees at the Sports Bar where we stopped in 2014.

From Buonconvento you continue on the SR 2 to the SP 14 which takes you directly into Montalcino and the crazy roundabout where I always get lost.  But  this time I took the right exit, turned left, drove past the Fortezza and along the wall to Piazza Cavour.


One of the reasons that this visit seemed like a case of ‘you can’t go home again’ was that it was very windy and chilly our first two days, something I’ve never experienced in southern Tuscany. That in itself limited some of our activities.   Montalcino and the neighboring towns are lovely and I enjoy just walking around.   But during our first two days we usually had to hustle to the car and get out of the wind.

Still we had some great experiences especially our last full day when we caught a break and had beautiful weather.

A Day Trip to Bagno Vignoni and Pienza

We left the hotel mid morning and from the parking lot, I backtracked to the roundabout and managed to get us on the road to Sant’Antimo (and  this year I found that I’d mispronounced it since my first visit).  That road takes you into Castelnuovo dell’Abate where I went straight when I should have turned left.  But I got us turned around and with only one more wrong turn got us into Bagno Vignoni.  While there’s now a rather odd metal sculpture in the ‘pool’ which I think detracts from it, the town itself is as beautiful as ever.  Plus it was more protected from the wind than Montalcino, so we spent at least an hour there, walking around, taking pictures.

From Bagno Vignoni  I drove us to Pienza (again with one wrong turn but better than expected).   The wind was even worse in Pienza and while looking for a parking space we saw that a tree had blown down on several cars.  So we hustled from the car into the centro.  We immediately wanted to get out of the wind so after a bit of a search, we found a little trattoria called ‘La Griglia’ that was open and had a table available.  My sister and I shared a burger and grilled chicken plus had a nice chat with a couple from Ft. Lauderdale.

There weren’t many shops open so we walked to the wall finding it surprisingly sheltered and pleasant.  We both got several nice photos and really enjoyed the walk back to the porta that leads to the main street going through town..


I first came to Sant’Antimo on a 2002 bike trip in Tuscany, my first introduction to the area.  I thought it was stunning and have returned several times writing about it in my Cathedrals and Abbeys post.

On our last day in Montalcino, a Friday, the wind finally died down and it was spectacular, the Tuscan blue skies I love, pleasant temps…  We had breakfast, during which I got directions to the vineyard, then I drove us to Sant’Antimo which requires driving to Castelnuovo dell’Abate, then making a sharp turn down a gravel road to the abbey.

There were more people than I expected but it was still amazing.  We walked around the outside, taking pictures, went through the garden Garden at Sant'Antimo and then the interior where I lit a candle for the boys.







Paradiso di Cacuci

I’m not sure of the connection between Albergo Giardino and Paradiso di Cacuci but I’ll be forever grateful to the manager (owner?) of the albergo for offering the free tour.  We made a reservation for Friday afternoon and lucked out with a beautiful day, the best of the entire week.

The drive there was terrifying though, mainly because the manager of the Albergo told us to take the street past Piazza Cavour, then turn left and keep going.  That street took us through a ‘porta’ so narrow we almost scraped the rear view mirrors on the side.  Then we continued down a narrow dirt road with drop offs on one side and a wall on the other.  We were sweating bullets by the time we spotted the vineyard.

As we parked a man got out of the car next to us, introducing himself as Francesco.  His card says he’s in charge of public relations, the perfect job for the quintessential Italian charmer.  After talking a bit about his background, including working in the U.S., he told us about the vineyard itself including the fact that it’s organic as are all the other vineyards in the valley, something he said was made easier by the biodiversity of the area. According to Francesco having mountains, forests and vineyards all in the same area, with deer and wild boars reduces the need for pesticides.

He also talked about the costs of buying even a small vineyard (one million euros per hectare, I think) and how many of the local vineyards have foreign investors, which sadly means Dubai, Russia etc..

Then he gave us the history of how Montalcino became the Brunello capital of Italy, or at least his version.  According to Francesco a mayor of Montalcino had a vision of turning Montalcino and the surrounding valley into one of the top wine growing areas in Italy.  Instead of courting industry as so many towns were doing at that time (in the late 1950’s, early 1960’s I think), he brought together the top producers of wine at that time and created a consortium which in turn set up stringent regulations that are followed today.

I’ve searched for information about the mayor but haven’t found any.  Most articles say that the region grew when in 1966 Brunello was granted the DOC (Denominazione di Origine). Then in 1980 Brunello became the first wine in Italy to obtain Denominazione di Origine Controllata e Garantita status.

I’ve never truly understood the difference between DOC and DOCG but found an excellent article at

According to Wine Spectator, ‘DOC wines are regulated for not just the type of grape and where they are grown, but also harvest yields, alcohol levels and the use of barrels. The rules for DOCG are even stricter than DOC—yields must be lower and the wines must be aged in barrels longer, for example. And DOCG includes requiring the wines be submitted for technical analysis and tasted for approval by a government committee before they can be sold as DOCG wines. The DOCG wines even have a numbered, government seal across the neck of the bottle to prevent counterfeiting.’

Some articles also credit the Mariani family from New York who started Banfi Winery with playing a big role in the development of the region’s wine making as well as in the local economy. (And Francesco said the same thing when we mentioned how disappointed we were that Castello Banfi is no longer open for wine tastings.)

We, then, went into the fermentation and ‘aging’ rooms where Francesco explained the process for making Brunello as well as their experiments with different Super Tuscans. As you can see in the gallery below there were some odd looking fermentation barrels that were part of their experiments.

He also described the multiple tests their wines have to go through to receive the DOCG. During that discussion he said, ‘We believe in science.’  We quickly agreed and tried to distance ourselves from the crazies in the U.S.

Our final stop was a stunning tasting room where we had 3 Brunellos, including one that Francesco said was their best year, plus a Super Tuscan and a Rosso di Montalcino.  While tasting the wines and having a few bites of salami and cheese, Francesco also told us the vineyard has a B&B on the grounds.  What a fabulous place that would be to stay. We ordered a half case of wine and now wish we’d bought more.

Where to Eat and Drink

Enoteca di Piazza/Taverna di Baietto

After the major letdown of finding that our former favorite restaurant was no longer good, (see Where Not to Eat, below) the Enoteca and Taverna became our home away from home. (As a side note, the enoteca and taverna are basically the same operation.)

Our first afternoon in Montalcino, we were starving so braved the winds and walked from the Albergo to Taverna di Baietto and had a couple of glasses of wine along with a caprese salad and crostini. After our day trip to Pienza, and finding that Castello Banfi is no longer open to wine tastings,  we drove back to Montalcino, cleaned up a bit, then walked down to Enoteca di Piazza and asked about a ‘degustazione’ which I mangled.  The staff suggested having it at Taverna di Baietto and so we each had 3 tastings, a meat tray and another glass of wine.

Our last day, after our wine tour at Paradiso, we had an early dinner here of excellent pastas and lots of wine.  Service is always pleasant and the food and wine are always good.

Where not to Eat and Drink

Il Grappolo Blu

I first ate at il Grappolo Blu on my 2002 bike trip and returned in 2010 and 2014.  (Our brief stop in Montalcino in 2016 only allowed us to have a quick lunch.)  I’ve always loved it, both the warm atmosphere and the great food. (see Places to Eat post).  So as soon as we were settled in our B&B, we asked the manager if she would make a reservation.

Our reservation was relatively early, around 7:30 pm, I think, and I was surprised to see a large number of people waiting to go in.  As soon as we walked in the door, I knew it would not be the same restaurant.  Instead of the small cozy room there was a large, cold addition with tables separated by plastic dividers.  Naturally we were seated there.  It took forever to get waited on and the service continued to be inattentive at best for the rest of the meal.

I ordered one of my favorites, Tuscan beans and sausages, and it was nearly tasteless.  My sister ordered ribollita and grilled vegetables and indicated her meal was mediocre at best.  The worst part was finding a huge list of very expensive wines instead of the usual house wines.  We ordered a half bottle of what was supposed to be their house wine and were charged 30 euros for it.

I wrote an extremely negative review.

Banfi Wineries

Like il Grappolo Blu and Sant’Antimo, I’ve been coming to Banfi since my 2002 bike trip and shared it with my sister, niece, and daughter.  (see Vineyards, wineries and enotecas post)  So as I drove us back to Montalcino from Pienza, I suggested driving to Banfi for a tasting.  We’d gone at least 15 km before I was fairly sure we were on the right road.  To our shock and dismay though, the road to Banfi Castello is now blocked by a huge industrial building, with a sign saying ‘Cantine.’

We were so disappointed in not being able to go to the beautiful Castello Banfi tasting room, that we drove back to Montalcino and went directly to Enoteca di Piazza.

Where to Stay

Albergo Giardino

   I was beginning to have a lot of doubts about Albergo Giardino before we arrived.  Despite having been in Montalcino several times, I was having difficulties visualizing where it was located despite putting the address into Google maps. So I was really nervous about driving there, knowing how confusing Montalcino can be and sent two emails to the management, never receiving a response.

When we arrived in Montalcino, we drove along the wall and then down and around Piazza Cavour without seeing the Albergo.  So we paid to leave our car in the closest parking lot and walked back down to the piazza.  As we came around the corner, my sister spotted it on the right, directly across from the piazza.  We were fairly daunted though when we walked in and saw a steep flight of stairs.  Seeing no one around, we hiked upstairs, finally hearing voices, then meeting the woman who owns or manages the hotel.  Albergo Giardino

She first showed us two rooms, giving us a choice.  We decided on the one with the larger bathroom which turned out to be a great choice.  Then she took us downstairs to what I had originally thought was an office for a vineyard but was also the hotel office and breakfast room.  After checking us in, she gave us a parking pass for the lot where we had already parked, telling us to bring the car to the front of the hotel, then unload and take it back to the same parking lot.

We were stunned but pleased when she lugged our heavy bags upstairs. But despite the steep stairs we were very happy with our room.  It was large, modern with comfortable beds and best of all heat including heated tiles in the bathroom.

Breakfast was the typical Italian meal of fruit, rolls and coffee but everything was fresh and the cappuccino was delicious.

The absolute best part of our stay was that she offered us a free wine tasting at Paradiso di Cacuci which was wonderful.

Despite some of the disappointments, especially the weather and some of our favorite places having lost their charm, southern Tuscany has a beauty and ambiance that will bring me back again and again.



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