Exploring the Historic Charm of Siena with My Spouse

A Day of Discovery in Siena

Today, Elena and I ventured beyond the well-trodden paths of Siena, seeking out the city's lesser-known treasures. It was a day filled with history, art, and the simple pleasures of Tuscan life. I'm excited to share our experiences, hoping to inspire you to explore beyond the typical tourist spots and find your own hidden gems.

Our day began, as many do on vacation, with a hearty breakfast. We enjoyed a delightful meal at PARTICOLARE di Siena. The restaurant had a sustainable approach to its cuisine, which I appreciated. Elena enjoyed a gluten-free option, and I savored a traditional Tuscan dish. The ambiance was charming, setting a perfect tone for the day.

Fueled and ready, our first stop was the Porta Romana. This magnificent gate, one of the main entrances to the ancient city, immediately captivated us. Built in the 14th century, its weathered stones whispered tales of centuries past. As we approached, the sheer scale of the structure was impressive, adorned with intricate designs and sculptures.


Explore Porta Romana, a historical landmark in Siena, Italy, where stunning architecture meets medieval charm in the heart of Tuscany.

The Porta Romana, also known as Porta Nuova, was constructed in 1328. Before it was built, the Convent of Santa Barnaba took up this site. It substituted the Porta di San Martino. The Porta Romana consists of two parts, the actual gate and an antiporto. The antiporto is another, external gate, providing extra protection. Both gates are crowned by merlons.

The outer facade is characterized by two stone wolves, and I learned that the gate once featured a fresco of the Coronation of Mary, painted by Taddeo di Bartolo, Sassetta, and Sano di Pietro. Though the fresco is now housed in the Basilica of San Francesco, standing there, I could almost picture it in its original glory. Elena and I took our time, snapping photos and soaking in the atmosphere. The gate stands as a symbol of Siena's resilience and beauty, a testament to the skilled artisans of the era. The entry of Porta Romana holds great significance as it is connected to the city of Rome and hence Papacy which provides an overall view of the Sienese countryside. I imagined countless travelers passing through this gate over the centuries, each with their own stories and hopes.

To walk through the Porta Romana is to step back in time, connecting with the countless souls who have passed through this gateway to Siena over the centuries.

Next on our itinerary was the Chiesa di San Cristoforo, located in Piazza Tolomei. This church, with its Romanesque origins, offered a serene escape from the bustling city streets. As we stepped inside, the cool, quiet interior provided a welcome respite from the July heat. The church's history is deeply intertwined with Siena's civic life. In fact, before the construction of the Palazzo Pubblico, the General Council of the Republic met here. It was in San Cristoforo that the Sienese decided to engage the Florentines in the Battle of Montaperti in 1260, a pivotal moment in the city’s history. The church’s facade, with its Neoclassical design, is quite striking.


Explore the serene Chiesa di San Cristoforo in Siena, a hidden gem showcasing stunning architecture and a tranquil atmosphere.

The original Romanesque style church with a Latin Cross layout was initially constructed in the 11th to 12th-century. Traces of Romanesque columns remain in the adjacent small cloister. During the 13th century, the cloister would host the council of the nascent Republic of Siena. It is claimed that at this site in 1260, a meeting took place between the Council of 24 and Florentine ambassadors. The latters demanded that Siena breach its walls, and allow Florentine fortresses in each Terzo. These heavy demands forced the former to decide that war with Florence was inevitable, and they dismissed the ambassadors, and prepared for war. They acknowledged the need to hire German mercenaries from Count Giordano d'Anglano, vicar of King Manfred, but lacked the funds. Upon hearing this, Salimbene Salimbeni, banker and founder of an early branch of the future Monte dei Paschi, merely walked to his nearby home, and returned to this cloister with the wheelbarrow full of 118,000 florins. The mercenaries proved essential to the Sienese victory at the Battle of Montaperti.

Elena and I admired the Madonna and Child with St Luke and Romuald by Girolamo del Pacchia, as well as the marble sculptural group depicting the Glory of St Christopher by Giovanni Antonio Mazzuoli. The church’s peaceful atmosphere invited contemplation, and we spent some time simply sitting and reflecting.

Our afternoon was dedicated to a visit to the Medici Villa of Lilliano Wine Estate. Although technically located in Florence, the estate promised a delightful escape into the Tuscan countryside, and it was well worth the short trip. As we drove through the rolling hills, the landscape transformed into a tapestry of vineyards and olive groves. The villa itself was stunning, a testament to the Medici family's love for beauty and refinement. The tour began with a walk through the villa's exterior, including the courtyard, panoramic terrace, and Renaissance garden. The views overlooking Florence were breathtaking, and Elena and I took countless photos.


Experience the elegance of the Medici Villa of Lilliano Wine Estate, where history, wine, and breathtaking scenery meet in Tuscany.

The tour includes a tasting of Malenchini wines as well as snacks like bruschetta and a Tuscan cutting board. At the meeting point you will meet the guide, who will accompany you on this journey to discover the Renaissance history of the Villa and its production of wine and oil up to the present day.

We then explored the historic cellars and the 17th-century orciaia (olive oil storage cellar), learning about the wine-making process from grape to bottle. The highlight, of course, was the wine tasting. We sampled three of the estate's most representative wines, each paired with local snacks such as bruschetta and Tuscan cheeses. As I swirled the ruby-red liquid in my glass, I couldn't help but feel grateful for the opportunity to experience such simple yet profound pleasures. Elena, always the responsible one, opted for non-alcoholic options but thoroughly enjoyed the snacks and the ambiance. I found myself particularly drawn to the Super Tuscans, comparing the vintages and savoring the complex flavors. It was a delightful immersion into Tuscan culinary traditions, made even better by the beautiful setting. I even considered signing up to be a winemaker for a day, but Elena reminded me of our packed itinerary.

As evening approached, we returned to Siena, ready for dinner. We chose Vivace Ristorante, drawn by its reputation for offering a unique view of the city’s landmarks. We secured a table on the outdoor terrace and were immediately rewarded with stunning panoramic views. The atmosphere was intimate, and the service was impeccable. The menu featured Italian dishes, and we decided to share a grilled salad, prosciutto, and spaghetti carbonara. The pasta was perfectly cooked, and the flavors were fresh and vibrant. For dessert, we indulged in tiramisu, a classic Italian treat. The combination of delicious food, fine wine, and breathtaking views made for a truly memorable dining experience.


Experience exquisite Italian cuisine at Vivace Ristorante in Siena—where every dish tells a story and every bite is a delight.

After dinner, we decided to experience Siena's nightlife with a visit to Maudit Pub. I had read about its quirky interior and decent selection of craft beers, and I was eager to check it out. The pub was indeed unique, with a warren of rooms and a lively atmosphere. I sampled a local craft beer while Elena enjoyed a non-alcoholic beverage. The pub was a mix of locals and tourists, all enjoying the relaxed vibe. While some reviewers mention uncomfortable seating, we found a cozy corner and enjoyed our drinks. The Maudit Pub offered a perfect end to a day of exploration, a chance to unwind and soak in the local culture.


Experience the vibrant atmosphere and delicious offerings at Maudit Pub, Siena's go-to spot for craft beers and gourmet burgers.

As we walked back to Hotel Minerva, the city was quiet and peaceful. The day had been a whirlwind of experiences, from ancient gates to serene churches and lush vineyards. I felt a deep sense of gratitude for the opportunity to explore Siena's hidden gems. Elena and I agreed that this was one of our most memorable days of the trip.


Discover comfort and convenience at Hotel Minerva, situated in the heart of Siena, close to attractions, dining, and public transport.

Tomorrow, we plan to visit the Basilica di San Miniato, Tempio del Brunello - Interactive Museum, and Sanctuary of the Madonna di San Biagio. I am particularly excited about the interactive museum, as I am keen to learn more about Brunello wine. We'll also be dining at Osteria Babazuf Siena for breakfast, Ristorante La Finestra for lunch, and La Vecchia Taverna di Bacco for dinner. And, of course, we'll be sure to make time for a little shopping at Il giardino di Rubegni Beatrice.

Before drifting off to sleep, I reflected on the day. Siena had revealed its charm in unexpected ways, offering a glimpse into its rich history and vibrant culture. It was a reminder that the best travel experiences often come from venturing off the beaten path and embracing the unknown.

There are several events happening in Siena that are related to the Jubilee 2025, including guided tours such as "Banks and Banking from the Middle Ages to Modernity" and "Historic Shops of Siena."

I look forward to sharing more of our adventures with you tomorrow. Until then, arrivederci!