Just in time before the summer holidays start, I am here with some more ideas for visiting Tuscany. This time, I will take you to some beautiful places in the Southern part of Tuscany that we had a chance to visit during our lat summer holiday in August. And it was not just an ordinary trip. August in Southern Tuscany is alive with local festivals and traditions, offering a truly immersive cultural experience. If you’re looking to add a touch of authentic folklore to your Tuscan adventure, here are some ideas based on our journey. These lively feasts bring a unique atmosphere to the region’s medieval hilltop towns.
This isn’t meant to be a complete guide or a detailed report – rather, consider it an invitation to discover more about these types of events through the official Tuscany tourism website.
We drove to Tuscany from Belgium via Como, but if it is too far or you don’t feel like driving a long distance and then road tripping around the region, you can always rent a car locally once you’re there.
You can either search for a hotel or Airbnb in some of the bigger cities or you can go more authentic with staying at some amazing holidays homes/Tuscan villas. We stayed at Borgo Villa Certano near Siena and you can read about our experience here.
And now let’s dive into the festive places we explored in Southern Tuscany together, shall we?
Siena and its Palio horse race
Located in the very heart of Tuscany, this stunning medieval town is a home to the worlds’ oldest bank – Banca Monte dei Paschi di Siena. It had been on our wishlist ever since our previous summer in Tuscany, so it became the first stop on our next Italian adventure. And actually we arrived in Siena just as the famous Palio feast was taking place! If you are searching for a very authentic Tuscan summer experience, this is it! Palio is a feast with medieval origins and probably the most known horse race of Italy. According to the Tuscany tourism board, it is also Tuscany’s most awaited summer event!
Palio of Siena takes place twice a year and lasts 4 days (June 29 to July 2 and again August 13 to 16). The main race takes place on July 2 and August 16 (no matter what day of the week) on the central square Piazza del Campo, where you can watch it from tribunes if you purchased a ticket. Each year, 10 out of 17 districts (contradas) compete in the race. The town is dressed for this special event: flags of different districts are hanging in the streets and residents proudly wear scarves with their district’s emblem. The race is preceded by a grand historical parade and followed by lively community dinners in the streets. It is very busy but fun time to be in the city! That said, be prepared as it gets quite crowded and finding a place to eat in the evening without reservation is nearly impossible in the center.
We came back another day shortly after the feast to discover more of the town and enjoyed a walk in relatively calm “post-Palio” Siena. And of course, we could not leave without souvenirs such as three scarfs with porcupine. 
Some places discovered and loved in Siena:
- L’Eerborario store for lovely Italian perfumes and phytocosmetics
- Buti pasticceria for very sweet breakfast of coffee break (located outside of the walled city)
- La Taverna di Giuseppe for typical Tuscan dinner in charming interior with stone and wood in a cellar from the Etruscan times
Stepping back in time in Volterra during Volterra AD 1398
Volterra, often referred to as the City of Alabaster and a place rich in Etruscan heritage (to the point that it houses museum devoted to the Etruscan legacy – Museo Etrusco Guarnacci). Every 2nd and 3rd Sunday of August, the Volterra AD 1398 feast is being held there. As the name suggests, it brings back the atmosphere of Middle Ages times to the town. What can you expect? Historical parade of knights, ladies, jugglers, falconers, musicians, merchants, and peasants passes through the city and is a great spectacle on its own. For special guided walks, workshops, and tournaments, you need to purchase a ticket. You may also need to purchase a special currency “gross” in order to shop for food and drinks at the main square (but in normal restaurants and bars they accept euros or cards).
We arrived in the late afternoon, and the atmosphere was already buzzing. It was loud and lively – maybe a little too much for us at that moment. As Adeline was tired, it was very hot and so we only enjoyed the procession, walked the streets of the old town after the crowds passed, and then found a quiet spot in the shade to relax with a cool drink. But maybe one day we’ll be back to experience it fully.
Quick stop at San Gimignano
This small medieval hilltop town is known for its skyline of five towers and well preserved Romanesque and Gothic architecture. After a busy day in Volterra, we arrived in San Gimignano feeling a bit tired, so we opted for a relaxed glass of wine on one of its smaller squares and a quick walk through the city center it was – nothing more, just enough to soak in the atmosphere. And then we finished the day with a dinner at a random restaurant on the central square.
Rolling barrels and a taste of Montepulciano during Il Bravìo delle Botti
Can you also see a bottle of wine in front of you when pronouncing this name? That’s no surprise as this town is probably most known for its red wine: Vino Nobile di Montepulciano, a red wine with the notes of deep cherry and plum which is made from the Sangiovese grape. But let’s put the wine aside for a moment – Montepulciano is really mesmerising on its own. This medieval hilltop town is rich in history and art, with origins dating back to the Etruscan and Roman times. Since the medieval ages, Montepulciano has become a cultural and architectural gem in the region.
Similar to our visit of Sienna and Volterra, here also we could submerge ourselves in a local feast. On the last Sunday in August, you can experience the very popular feast called Il Bravìo delle Botti di Montepulciano. Similar to Palio in Siena, this is also a race between several districts of the same town, although it’s not about horses but wine barrels – it actually replaced the medieval horse races. Athletes in the group of 2 run uphill the steep streets of Montepulciano, rolling wine barrels of 80 kg in front of them, for about 1,8 km till the finish line which is at the Cathedral on the main square. Prior to the race, you can witness a historical procession passing through this hilly medieval town.
We arrived here already later in the early evening and somehow ended up having a typical Tuscan dinner with the locals. There was a selection of meals cooked and we needed to first buy some non-financial currency in order to buy food and drinks. The atmosphere was fantastic! After that we walked to the main square and witnessed last athletes arriving with their barrel, then when walking back to the car we still could hear guys running and rolling the barrels downhill. Very original event to experience, I have to say. We pretty much enjoyed, even though it became a little late for Adeline – but somehow, she was as enthusiast as us until the moment of getting in the car…
Pitigliano in Renaissance glory during Festa della Contea
This was the cherry on top for us during our stay in South Tuscany. This medieval town built on a top of a tuff promontory, with its tiny streets and houses old enough to tell countless stories, is not far from a wonder. As we wandered, we were mesmerized by the breathtaking views – not just of the landscape, but also of the tuff rock formations that the town’s buildings cling to. We enjoyed interesting small boutiques selling local artisanal products.
When we arrived here it looked like we were actually stepping back in time straight into the Renaissance. As we were entering the town, a procession composed of musicians, ladies and lords dressed elegantly, followed by jugglers and dancers. Further we could watch a belly dancer and a juggler doing their performances. Once we entered the center of the town, the crowd of counts was back with the Renaissance dances and live music. People were watching, applauding, it was an amazing and fun atmosphere, but still not too wild. Later we learned that it was the Festa della Contea which takes place three days every second half of August in Pitigliano. It includes folklore performances with live music but also a County market with art, culture and ancient crafts related objects, County banquet with tastings of wine and local food, and Palio dei Rioni which is again a competition between the districts of Pitigliano.
We had a dinner at Il Tufo Allegro which was a pleasant experience, though perhaps not quite worth the price. But we were keen on sitting outside and the choice was limited. I liked their interior though. The other day we ate at Angiolina where I had my favourite sage butter ravioli – a simple, delicious dish that hit the spot.
Thanks for reading and I hope you enjoyed this festive journey through Southern Tuscany with us! What about you, have you experienced any feasts in South Tuscany? I’d love to hear your stories – please share them in the comments below so that other readers can also benefit from your tips! Thank you in advance for sharing your experience!
In this post, we explored Siena, Volterra, San Gimiano, Montepulciano, and Pitigliano. But that’s not all – I will be dedicating further posts to Val d’Orcia and the Maremma separately. So if you are planning your next holidays in Tuscany, stay tuned! And bye the way, did you know you can subscribe to my newsletter to get the new posts directly in your mailbox? Newly, you can also follow me on Substack now for updates!
Příspěvek Festive August in Southern Tuscany pochází z 1001 Voyages Gourmands
