Siena Travel Guide: Rainy Day Adventures, Food & Local Traditions

Itinerary:

• Regional train. No first class. No reserved seating

  • You can bring your own food and eat in the train

    • Validate tickets before boarding the train and one of the machines outside the train itself

    • All train tickets purchased online are already validated. Only (paper) tickets purchased at the train station need to be validated (date/time stamped)

• Train ride is about an hour and a half

  • There is a taxi rank right outside and the journey is not long and they take you close to the Piazza Del Campo. It cost 12 Euro, so if you don't mind the extra cost or you're in a larger party, just take the taxi.

    • Piazza Del Campo to Siena train station taxi ride - 14 Euro

• Self Walking guided tour

  • https://www.bigboytravel.com/italy/siena/free-walking-tour/

• Lunch: Bar Ristorante Fonte Gaia

• Mid-afternoon coffee: Nannini Dolci e Caffe

Palazzo Pubblico in Siena, Italy, on a rainy day, showcasing the iconic medieval architecture and towering clock tower

With the train station just 5–10 minutes’ walking distance from our hotel, we had time to enjoy breakfast before heading to the platform without rushing. Navigating the station was seamless, and soon we were on our way to Siena, one of Tuscany’s most picturesque medieval cities.

Known for its UNESCO-listed historic center, Siena invites visitors to explore its stunning Gothic architecture, winding cobblestone streets, and the famous Piazza del Campo. Its compact and walkable layout made it effortless to take in the city’s cultural heritage and timeless charm—a must-visit destination in Tuscany.

Everything I had read in vlogs and blogs confirmed that Siena is highly walkable, but one blog stood out in particular, offering a detailed walking route, complete with pictures and historical notes. It removed the hassle of extensive planning and proved to be remarkably precise when followed.

The Rain’s Unexpected Beauty

The rain lasted all day, but rather than being an inconvenience, it intensified Siena’s atmosphere. Wet cobblestone streets reflected the soft light of the overcast sky, while Gothic facades loomed starker against the gray backdrop. The steady drizzle gave the town an air of mystery, emphasizing its medieval history rather than distracting from it.

I had wanted to visit Siena for years—ever since I started following Rick Steves after graduating from college. His travel insights shaped much of my interest in Tuscany, and the idea of walking through narrow alleyways, past fortress-like buildings, and getting lost in the city’s history had been something I had imagined for a long time. Determined to take my time, I fully immersed myself in its architectural beauty rather than rushing through it.

A Taste of Siena

One of my culinary goals in Siena was to try Panforte, a dense cake packed with dried fruit, nuts, and spices. It was easy to find throughout the city, so I picked up a few for souvenirs and finally tried it when I got home. Its chewy, firm texture carried an intense sweetness that lingered—an acquired taste but undoubtedly distinct.

For lunch, we opted for a sidewalk café in Piazza del Campo, the famous medieval square—home to the renowned Palio di Siena horse race. As I sat there, I imagined the energy of the square during the Palio, a spectacle I knew I wanted to experience in person someday. Dining in major squares could be hit or miss, often prioritizing the view over the meal. That was the case here—the atmosphere was spectacular, but the meal itself was forgettable.

Later, we stumbled upon Nannini, a café that has been open since 1910. Bright and inviting, the space overflowed with pastries and baked goods. The coffee portions were generous, though the service could have been better. A quick turnover meant tables were easy to find, and unlike most places we had visited, the bill arrived automatically. Despite the service, the quality of the pastries made the stop worthwhile.

A Celebration in the Heart of Siena

By late afternoon, Piazza del Campo came alive with university graduates celebrating alongside their friends and family. Wearing laurel crowns or flowers, they chanted cheers before bursting confetti into the air. Some played games unique to their groups, adding to the revelry.

The University of Siena sits right in the historic center, blending medieval grandeur with student energy. I was too caught up in the moment to record it, but watching the graduates celebrate in the middle of a town that has existed for centuries was a striking reminder of the interplay between past and present—one of the many things that makes Siena so special.

Returning to Florence

The train ride back was uneventful. We arrived at Siena’s train station about 15 minutes before departure, avoiding any stress. I had intentionally chosen an early return time to allow for plenty of rest, knowing that the next day’s itinerary had an early start.

Instead of sitting down for dinner, I opted for takeaway pizza near the hotel. Wanting to try a Florentine-style pizza, I found a pizzeria café close to the train station. The pizza choice? Cheese, mortadella, pistachio, and mozzarella—delicious! Pistachio was everywhere in Italian cuisine (at least for that season), and since it’s one of my favorite flavors, I made sure to try it whenever I could. We also ordered tiramisu, though I don’t remember how it tasted. Strangely, I hadn’t vlogged the pizza or tiramisu, despite capturing so much else from the day.

Final Thoughts

Siena was everything I had imagined—historic, atmospheric, and rich in tradition. Even with the steady rain, the town’s beauty remained unshaken, its medieval streets, timeless architecture, and vibrant university celebrationscreating an unforgettable experience.

📍 Follow along for more recommendations and insights into Italy’s most captivating destinations!