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Following a fabulous stay at La Posta Vecchia (which you can read about here) we set out for a couple of days in Tuscany and Umbria. Our time spent in Tuscany was spent at a private home, so no review of it here, but just some highlights of towns we explored during our visit.

First off, the decision was made to have AutoEurope deliver a car to us at La Posta Vecchia, and we specified an Audi with automatic transmission. After we checked out and were told the car had arrived, our eyes immediately went to the Ferrari in the courtyard. Perhaps our travel agent had arranged for un upgrade?! Unfortunately that car was for someone else, and our eyes were drawn instead to the grey VW T-Roc off to the side. It was indeed automatic, and as the agent who delivered it reminded me, Audi is a subsidiary of VW. Because I was so relaxed following our stay, I didn’t flip out as I often do. I understood that if we wanted to exchange the car it would take several hours, if they could even locate the car I had specified. We had an agenda for the day so we examined our T-Roc for damage (quite a big dent on the side which we photographed and made the agent note on her form- I didn’t trust her or AutoEurope a bit) and we were on our way.

Because the T-Roc didn’t have a port to plug in our iPhone, we made a quick stop at an AutoGrill, a chain of rest stops like nothing you will ever find in the states. Everything is spotless, and presented in such an enticing way. My husband couldn’t resist a panini ( and some cookies) and of course the charger adapter we came in for.

We headed off in the direction of The Mall a very high end outlet mall which features every luxury Italian brand you can hope for. It was sort of on our way to our destination in Montalcino, just a small detour.

We had some good success in the outlet, unfortunately not in Gucci as I hoped, but in Etro and Prada. If you are in the vicinity and like to shop, be sure to add this stop to your itinerary. This is actual designer merchandise from recent seasons, not items made just for the outlets like you find in the States.

Our first stop in Tuscany was at our favorite vineyard in Montalcino, Cerbaiona, purveyors of superb Brunellos. While not open to the public, we were able to enjoy a tour and a visit to the facility whose recent construction and updating is just about finished. We met with the winemakers Matthew and Andrea and managed to sample a great deal of wine.

Following our wine tasting we wandered around the atmospheric hill town of Montalcino before settling on Il Grappolo Blu for a tasty dinner. Upon entering the small homey restaurant we noticed an extensive series of plexiglass dividers which served as a reminder of just how affected Italy was by Covid. There is no longer a mask mandate in place, but some of the folks we encountered in the countryside were still adhering to the old rules. We thoroughly enjoyed ourselves at Il Grappolo Blu, especially the Tuscan specialty Pinci pasta (thick hand rolled noodles) and the perfect rendition of Caprese Salad. Of course they had a fabulous wine list as well. We walked a bit following dinner, to aid in digestion, and found just enough room for some Gelato (surprise surprise). Gelateria Artigianale e Yogurteria “WhyNot” was homemade and delicious.

We didn’t feel as though we covered every inch of Montalcino in the evening, so we returned in the daytime to explore some more. Italy was experiencing the same heatwave as the rest of Europe while we were there, with temperatures hitting 100 degrees F every day of our trip. We were not dissuaded from walking due to the extreme heat, we just walked a bit slower. After clocking several miles we stopped for lunch at La Sosta, a wine bar located in close proximity to the Fortress, and filled with locals and tourists alike. We sat outside, and were ultimately underwhelmed by both the service (or lack thereof) and the food. It wasn’t bad, but a very strong eh.

To make up for the average meal I stopped at Farmacia Salvioni, a pharmacy dating back to 1905 which carries many super Italian beauty lines including their own, as well as my favorite, Santa Maria Novella dal 1221. It was a perfect opportunity to stock up.

Our next town to explore was Pienza, located between Montalcino and Montepulciano. Pienza stands out because it is the epicenter of Pecorino cheese; the town is so filled with cheese that the smell is intoxicating as you amble down the main street. To be honest, Pienza is pretty close to heaven! Before we got to the town itself we made a quick detour to see the Vitaleta Chapel located in the Val d’Orcia, one of the most picturesque Chapel’s you could ever hope to see. It is tiny, but stunning; well worth a detour.

First stop in Pienza (even before the cheese) was the Cathedral of Pienza, which along with the historic center of Pienza is considered a Unesco World Heritage Site. The Cathedral and its surroundings are quintessential examples of Renaissance architecture and urban planning circa the mid 1400’s. I am not sure how we missed Pienza in the past, but it truly is a magical town worthy of a visit.

The photos below say it all: cheese, cheese, and more cheese- every variety of Pecorino you could dream of, and the aroma!!! A great article about these fabulous cheeses can be found here. The best of the many cheese shops we went to was La Bottaga Del Naturista (where you could also pick up sandwiches), but truth be told, they were all pretty terrific.

There are numerous other temptations in Pienza including some pretty stellar Porchetta (excellent sandwich from Nannetti e Bernandini,) and of course, Gelato!

One of the highlights of our stay was a day trip to Siena. The last time we had been there was in 2006 when we spent a month in Umbria. We specifically wanted to return to Antica Pizzicheria al Palazzo della Chigiana dal 1889 where we had experienced a special moment with the proprietor Antonio De Miccoli on our youngest son’s 5th birthday and which has become one of our family’s favorite travel memories. The shop, located just steps away from the Piazzo del Campo enjoys a stellar reputation as purveyors of the highest quality cheeses, charcuterie and wine, but also reputedly has a very particular and bossy owner. As it turns out the part about the excellence of the food is spot on, but Antonio is a gem.

Back in 2006 we entered the tiny shop with our boys, and because it was the day of the Palio we were all decked out in the colors of the local Contrade (city wards). My youngest was wearing the scarf of the owner’s Contrada so he took a special liking to him. When he learned it was his birthday he closed the shop (there was a sizable line outside as per usual) and found a tremendous red balloon to blow up and present to my son. This was, as you can imagine for a 5 year old boy, pure magic! The ballon plus colossal meat and cheese packed sandwiches made for an unforgettable experience.

When we lined up 16 years later we were thrilled to see Antonio still behind the counter (albeit a bit older, as were we). We showed him our photo and let him know what an important part he has played in our memories. He was so touched, we spoke for a while about the passage of time, and he then created a feast of cheeses, meats, bread and cookies for us to enjoy outside in the alleyway adjacent to the shop. When we returned inside to say thank you, we presented Antonio a bottle of vintage Brunello as a thank you. He was so moved, and we have since stayed in touch via email. I imagine this could have happened anywhere, but to me it is a quintessential Italian experience, and the reason we come back year after year.

If you are anywhere near Siena get yourself to Antica Pizzicheria and be sure to have a hefty appetite. You will thank me!

Following our reunion we explored a fabulous Dali exhibit just across the street. Not only was there a vast collection of Dali’s work, we learned it was all for sale. The show takes place in a gorgeous palace, so it was fittingly surreal

Continuing our exploration of Siena, which was indeed a trip down memory lane, we paid a visit to the magnificent Duomo di Siena, the Piazzo del Campo where the Palio is held each year, and even got to witness members of the Onda Contrade marching through the Campo practicing for the big day. As mentioned before, the temps were hovering around 100 F so those men in tights must have been awfully hot. We ended our day with Gelato from Nannini, an atmospheric pastry and gelato shop (they serve alcohol as well) in the center of town. The Gelato was good, but I made the mistake of visiting the rest room after we finished and it was HEINOUS- filthy, awful. Not sure what went on there, but I wish I could unsee it. For this reason I would skip the Gelato from Nannini in the future.

Continuing our exploration of Umbria, we paid a visit to Todi, a charming hill town which is where we had rented a house back in 2006. We had to visit all our old haunts, the Piazza, the Gelato spot, the Grocer Marcelo Giovenali , and our Pizza place Ristorante Cavour.

We must have dined at Cavour eight times during our month long stay back in 2006; it was that good. Keeping in mind that it was still exceedingly hot, we opted to eat outside on their lovely terrace. At first we were seated next to a fan that seemed to be spraying a fine mist towards us in an attempt to cool us down. We convinced ourselves we would likely contract Legionnaires disease, so we asked to move tables. Once we were settled in to our “safer” location we ordered a Truffle Pie, some wine (Lungarotti Rubeso– a classic and very affordable Umbrian vino) and an Insalata Maxi (similar to a Salade Nicoise but with some Mozzarella thrown in). The food was delicious, though the service a bit distracted (it may have been the intense heat). We chatted with the owner about having first visited back in 2006, and here again we were welcomed as old friends.

Perugia was another town we chose to return to, the capital city of Umbria. We had been to Perugia back in 2006, and it seemed worth a revisit, but unfortunately we were terribly disappointed. The town was rundown, dirty, and there were a large number of homeless. While it is a University town, summer had started and it seemed somewhat deserted. After a visit to the Maggiore Fountain (beautiful) , the Piazza IV Novembre, and the Cathedral of San Lorenzo we grabbed some candy (Perugia is filled with candy shops) and returned to the car park which we attempted to exit. Unfortunately upon trying to pay at the kiosk (we ultimately paid twice) we learned the entire system was on the fritz and we, along with several others were trapped inside. We called for assistance numerous times using the call number provided only to be met with recordings that there was no one available to answer our distress call. Twenty minutes passed, and finally we had the clever idea to take a ticket to enter, and escape while the barrier went up to let a car in. We set the stage for others to follow, and I am sure we are on camera doing so. Hopefully the Italian authorities don’t trace us back to the rental car and charge us with some sort of infraction. That was the icing on the cake, Perugia got the thumbs down from both my husband and I.

There is so much to explore in both Tuscany and Umbria, this is just a sampling. If you are visiting the region, I would say that Montalcino, Pienza and Siena are towns you most certainly want to include on your itinerary. We ended our vacation in a tiny Umbrian town, Lisciano Niccone, at one of the most incredible places we have ever been. Stay tuned for the review!