Siena is one of those places that feels like stepping back in time. Tucked away in the heart of Tuscany, this medieval city offers more than just beautiful architecture – t’s filled with history, culture, and some of the best food you’ll ever try in Italy. Whether you’re a history buff, a foodie, or someone who just enjoys wandering through picturesque streets, Siena has a way of capturing your heart.
This past August, I visited Siena for the first time and walking through its narrow cobblestone streets, feeling like I was part of an ancient world. The town has this relaxed charm, but at the same time, you can feel the energy of centuries of tradition, especially when standing in Piazza del Campo, the main square. It’s the kind of place where you can spend a whole day exploring, learning, and of course, indulging in delicious Tuscan cuisine.
If you’re planning a trip to Tuscany, Siena is a must-see. In this guide, I’ll walk you through the perfect day in Siena, focusing on its iconic Piazza del Campo, local traditions like the Palio, and the classic Tuscan dishes you just can’t miss. Ready to experience the charm of Siena? Let’s dive in!
Morning: Piazza del Campo – Heart of Siena
Start your day in Siena at its very heart: Piazza del Campo. This stunning, shell-shaped square is not only the physical centre of the city but also the cultural and social hub. As soon as you step into the piazza, you’re greeted by a sweeping view of centuries-old architecture, with the towering Torre del Mangia and the grand Palazzo Pubblico dominating the scene. It’s the perfect place to get a sense of Siena’s rich history and vibrant community life.
The square’s unique shape isn’t just for show – it’s designed to draw your eyes toward the Palazzo Pubblico, Siena’s city hall, which has been the centre of political life since the Middle Ages. For the best view of the city, I recommend climbing the Torre del Mangia. It’s 400 steps to the top, but trust me, the panoramic view over Siena and the rolling hills of Tuscany is absolutely worth it.
One of the most fascinating things about Piazza del Campo is its connection to the Palio di Siena, a historic horse race that takes place twice a year. The Palio isn’t just a race; it’s a symbol of deep-rooted tradition and fierce neighbourhood rivalries. Even if you’re not visiting during race season, you can still feel the energy that surrounds this event by visiting the Civic Museum inside the Palazzo Pubblico, where you’ll find paintings and artifacts that tell the story of Siena’s past.
Spend your morning soaking in the atmosphere of Piazza del Campo, sipping a cappuccino at one of the many cafés lining the square (before 11am of course), and watching the world go by. Whether it’s the buzz of locals chatting or tourists marvelling at the architecture, this is the place where Siena’s soul truly shines.
Late Morning: Exploring Siena’s Medieval Streets
After spending time in Piazza del Campo, it’s time to lose yourself in Siena’s winding medieval streets. This was one of my favourite things to do this past holiday – there’s something magical about wandering through narrow, cobblestone alleyways where history seems to seep out of every stone.
Start by heading towards the breathtaking Siena Cathedral (Duomo di Siena). This Gothic masterpiece is one of the most stunning churches in Italy, with its striking black and white marble façade and intricate details that will leave you in awe. Take a moment to step inside and admire the elaborate interior, from the beautifully frescoed ceilings to the marble mosaic floor – a true work of art. If you have time, I highly recommend visiting the Piccolomini Library, located inside the cathedral, which is filled with vibrant frescoes that showcase Siena’s artistic heritage.
As you explore further, don’t be afraid to get a little lost. Part of Siena’s charm lies in its hidden corners and lesser-known spots. You’ll stumble upon charming little squares, artisanal shops, and cafés tucked away from the main streets. Take a moment to browse local boutiques for handmade ceramics or stop at a tiny gelateria for a refreshing scoop of gelato.
Siena’s medieval streets offer endless surprises, from beautifully preserved palaces to secret courtyards. It’s the perfect way to immerse yourself in the city’s rich past while discovering its present-day vibrancy. And since you’re already working up an appetite, you’ll be more than ready to dive into Siena’s culinary delights come lunchtime!
Lunch: Classic Tuscan Dishes to Try
By now, you’ve probably worked up an appetite, and you’re in for a treat – Siena is home to some of Tuscany’s most iconic dishes. For lunch, I suggest finding a cozy trattoria near Piazza del Campo or tucked away in one of the quiet side streets. You can’t go wrong with a simple, rustic meal here, as the city prides itself on using fresh, local ingredients that bring out the true flavours of Tuscany.
One dish you absolutely have to try is pici, a thick, hand-rolled pasta that’s a Tuscan specialty. It’s typically served with a rich garlic and tomato sauce (pici all’aglione) or with a hearty meat ragù. The texture is wonderfully chewy, and it’s the perfect comfort food after a morning of exploring. Another classic is ribollita, a traditional Tuscan soup made from leftover bread, vegetables, and beans. It’s a filling and flavourful dish that embodies the region’s ability to turn simple ingredients into something delicious.
If you’re in the mood for something more robust, go for the bistecca alla Fiorentina. While technically a Florentine specialty, you’ll find excellent versions of this thick-cut, grilled T-bone steak in Siena. It’s often cooked rare to bring out the natural flavours of the high-quality beef, and it’s usually served with a side of roasted potatoes or beans. Pair it with a glass of local Chianti, and you’ve got a true Tuscan dining experience.
For dessert, don’t miss the panforte, a Sienese specialty. This dense, spiced cake made with nuts, dried fruits, and honey is perfect with an espresso to end your meal. It’s a sweet taste of Siena’s long history, as the recipe dates back to the Middle Ages.
After indulging in these classic Tuscan dishes, you’ll not only be satisfied but also feel like you’ve experienced a true slice of Siena’s culinary culture. Trust me, food in this city is as much a part of the adventure as the sights!
Afternoon: Siena’s Cultural and Historical Sites
After a satisfying Tuscan lunch, it’s time to dive deeper into Siena’s rich history and cultural treasures. The afternoon offers the perfect opportunity to explore some of the city’s most notable sites that showcase its artistic and historical significance.
Start with a visit to Basilica di San Domenico, a striking Gothic church perched on a hill overlooking Siena. This basilica is famous for its connection to St. Catherine of Siena, one of the city’s most revered figures and a patron saint of Italy. Inside, you’ll find a relic of St. Catherine – the chapel dedicated to her includes her preserved head, which is both eerie and awe-inspiring. The basilica itself is simple yet imposing, with a sense of peace that offers a moment of reflection after a busy morning.
Next, make your way to the Pinacoteca Nazionale, Siena’s national gallery, which is home to an impressive collection of Sienese art from the Middle Ages and Renaissance. If you’re an art lover, this gallery is a must-see, as it features works by renowned local artists like Duccio di Buoninsegna and Simone Martini. The pieces here offer a glimpse into Siena’s artistic golden age, where religious themes and intricate details took center stage.
For a change of pace, take a stroll over to Palazzo Chigi-Saracini, a beautiful 12th-century palace that now houses the Accademia Musicale Chigiana, Siena’s prestigious music academy. While the palace itself is a work of art, you might be lucky enough to catch a classical music performance during certain times of the year.
If you’re looking for a more leisurely afternoon, head to the Fortezza Medicea, Siena’s fortress built in the 16th century. The fortress is now a public park where you can walk along the ancient walls, enjoy views of the Tuscan countryside, or even relax with a glass of wine from the nearby Enoteca Italiana, which offers an excellent selection of local wines. It’s the perfect spot to wind down and reflect on the day’s discoveries.
Whether you’re immersing yourself in art, history, or simply taking in the beauty of Siena from above, the afternoon will leave you with a deeper appreciation of the city’s cultural depth and timeless appeal.
Evening: Relaxing in the Tuscan Countryside
As the day winds down, it’s time to leave the bustling streets of Siena behind and embrace the tranquility of the Tuscan countryside. One of the best things about Siena is how quickly you can transition from the city’s medieval charm to the peaceful, rolling hills that surround it. Just a short drive or a relaxing walk along the city’s ancient walls, and you’ll find yourself amidst vineyards, olive groves, and breathtaking landscapes.
If you prefer to stay close to town, take a leisurely stroll along the Fortezza Medicea walls, where you’ll be treated to panoramic views of the surrounding countryside bathed in the soft glow of the evening sun. It’s a peaceful spot, perfect for soaking in the beauty of Tuscany as the day fades into dusk.
For a more immersive experience, I recommend venturing just a little further out of the city. Find a scenic viewpoint or a nearby village to enjoy the sunset. The Tuscan countryside is known for its golden light, and watching the sun set over the hills is nothing short of magical. If you’re a fan of photography, this is the time to capture some truly stunning shots of Tuscany’s iconic landscapes.
End your day with a visit to a local enoteca (wine bar) or vineyard. Siena is surrounded by some of the best wine regions in Italy, including Chianti and Brunello di Montalcino. Sip on a glass of local red wine, paired with some simple Tuscan bites like bruschetta, pecorino cheese, and freshly sliced prosciutto. There’s nothing quite like the taste of local wine enjoyed in the very region it comes from.
Whether you spend your evening reflecting on a perfect day in Siena or simply gazing at the stars from a quiet spot in the countryside, this is the ideal way to end your Tuscan adventure. You’ll leave with a sense of calm and fulfilment, having experienced not just the history and culture of Siena but the timeless beauty of Tuscany itself.
Siena’s charm is undeniable – from its medieval streets and rich history to its incredible food and stunning countryside. Whether you’re planning to spend a day or an entire week in this Tuscan gem, there’s so much to explore, and each experience offers something unique. But what truly makes a trip unforgettable is having an itinerary tailored to your interests, making sure you don’t miss any of the hidden gems that give Siena and Tuscany their magical appeal.
If you’re considering a trip to Siena or anywhere in Tuscany, let me help you craft the perfect itinerary. Whether you want to dive deep into the local traditions, savour authentic Tuscan dishes, or simply relax and enjoy the stunning views, I can plan a bespoke travel experience just for you. With my firsthand knowledge and passion for the region, I’ll make sure every detail is taken care of, leaving you to fully enjoy everything this incredible area has to offer.
Get in touch today, and let’s start planning your dream Tuscan getaway. Whether it’s your first visit or your tenth, I’ll make sure it’s one you’ll never forget!