Among the many charming places in Tuscany (and all of Italy), Siena stands out as a shining jewel. Visitors fortunate enough to come here will carry the memory of this enchanting city with them forever. Just an hour's drive from the magnificent Florence, Siena offers a more relaxed experience compared to its bustling counterpart. But don't be fooled by this tranquility. Some of Tuscany's finest artworks are hidden here.

At Destimondo, we rave about Siena, and we are not alone. Remember the spectacular chase of James Bond in the film 'Quantum of Solace' over the terracotta-colored roofs of Siena? This is exactly where the scene was filmed. Enjoy the unique atmosphere as you leisurely stroll through the historic Piazza del Campo , gelato in hand.

Imagine horses with thundering hooves galloping through the shell-shaped piazza during the famous Palio di Siena. And above all, take plenty of time to visit the impressive Gothic-Romanesque Cathedral – an architectural masterpiece that proudly rises into the sky. You can easily spend hours inside, captivated by its beauty.

In the evening, savor the excellent wines of the Val d'Orcia , such as the robust Brunello di Montalcino or the Vino Nobile di Montepulciano, in one of the wine bars. Combine this with a delightful, simple dinner in good company, and you will truly feel what it means to be in Italy.

Top 10 Highlights of Siena

Inspiration

Travel Information

How long should you stay?

A day trip to Siena is enough to visit the Piazza del Campo and the cathedral complex. However, since we simply love the flair, we recommend dedicating two days to Siena.

If you also prefer your accommodation to be in the city rather than in an agritourismo, Siena is perfect for that. The city is much more relaxed than Florence and offers an ideal location to explore the magnificent Tuscany.

Best time to visit

Visit Siena in spring or fall for pleasant weather and fewer crowds. September is particularly nice, with temperatures ranging between 18-25°C. October is cooler, but the autumn colours in the entire region are beautiful.

How to get to Siena?

Plane
The nearest international airport is in Florence. With the available trains, it is easy to reach Siena within one hour.

Train
Siena is well-connected and direct train services are available from Florence.

Car
To explore the region, a car is highly recommended. The road infrastructure is very good and you can easily arrive by car. A good option is to rent a car from the airport in Florence.

Be mindful of the ZTLs and park your car in one of the parking garages.

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Day Trips from Siena

Personally, we recommend to choose your home base in one of the many agrotourisms in the area. But if you prefer town life, Siena also makes a great and convenient home base to explore the region. Here are a few ideas for some excellent day trips:

San Gimignano

Known as the Manhattan of medieval times, this charming town is a perfect destination for a day trip. Roam through narrow streets, explore the picturesque Piazza della Cisterna, and ascend one of the town's well-preserved towers for breathtaking panoramic views of the Tuscan countryside. The Torre Grossa is the tallest tower to survive and is a great choice. With the same ticket, you can also visit the interesting town art museum. It's easy to miss, so we also want to mention the Romanesque church of San Lorenzo in Ponte. It is small, but has very creative frescoes of hell :)

Montepulciano

This cherished destination attracts thousands of tourists and wine enthusiasts alike. Perched on a hill in the famous Val d'Orcia, it casts a spell over its visitors with its medieval charm. Meander through the old town to uncover treasures like the iconic Piazza Grande and the Cathedral of Santa Maria Assunta. However, the true highlight undoubtedly is the Vino Nobile di Montepulciano. This exquisite red wine, made from Sangiovese grapes, has garnered global acclaim and is exported worldwide. Sipping a glass of this world-class wine against the enchanting backdrop is an absolute must-do. Montepulciano also serves as an ideal location for wine tastings, whether in the town itself or at one of the nearby wineries.

Montalcino

Discover the enchanting town of Montalcino, celebrated for its Brunello di Montalcino. Tour the historic fortress, stroll through the charming streets, and indulge in wine tastings to relish the flavours of this prestigious wine-growing region. If you find yourself torn between Montalcino and Montepulciano, we recommend the former. Honestly, we found it a more enjoyable day trip.

Volterra

Volterra is definitely a worthy destination. This distinctive walled city is constructed upon one of the Twelve Cities of the ancient Etruscan civilization. The imposing Medici Fortress dominates the city and gives it a distinctive character. Learn about the city's rich alabaster craftsmanship and browse for unique souvenirs. Notably, it has become a popular spot for fans of the Twilight series, as the town plays a significant role in the books written by Stephenie Meyer.

Chianti Wine Region

Embark on a wine-tasting adventure in the Chianti region, known for its picturesque vineyards and excellent wines. Visit local wineries, sample Chianti Classico wines, and soak in the beauty of the rolling vine-covered hills.

Pienza

A UNESCO World Heritage site, Pienza is a gem of Renaissance architecture. Explore the well-preserved historic center, admire the stunning views of the Val d'Orcia, and savour Pecorino cheese, a local delicacy.

Local Specialties

What to Drink

A quintessential part of Tuscan life revolves around savoring a glass (or perhaps two or three) of the exceptional regional wines. Delight your taste buds with world-renowned varieties like Chianti Colli Senesi, Brunello di Montalcino, Chianti, Vino Nobile di Montepulciano, and Vernaccia di San Gimignano (a celebrated Tuscan white wine), all sourced from local vineyards. Engage in discussions about the nuances of wine tasting as you explore the distinct flavors each brings to your palate.

What to Eat

Begin your culinary journey with the crostini neri di Siena, a typical appetizer. This rich spread, served on dry, broth-soaked bread, is a symbol of Sienese hospitality and graces the menus of many local restaurants.

For your primi piatti, try the handmade pici, Siena's signature pasta. Opt for the renowned pici all'aglione, seasoned with garlic-infused flavors, or explore variations featuring wild boar or Cinta Senese meat sauce.

Additionally, indulge in one of the many menu choices featuring truffles. For those, who usually don't like truffels, I dare you to try. I was so surprised by the difference between freshly cut truffles and truffle oil, which is usually used in other countries.

Moving on to richer courses, savor the Bistecca alla Fiorentina, a typical Florentine-style steak, or opt for the comforting Ribollita stew or Ossobuco alla Senese, a veal shank braised with vegetables and herbs.

Conclude your gastronomic exploration with the sweet notes of Cantucci biscuits, Ricciarelli, an almond treat infused with candied orange peel, or a classic Panforte, traditionally enjoyed during Christmas.

Restaurants Tips

• Ristorante La Locanda dei Tintori: fantastic restaurant serving authentic Tuscan cuisine
• Osteria Il Carroccio
• Osteria di Castelvecchio: charming osteria with a nice terrace
• Osteria da Divo: Elevated regional dishes and fine wines in a medieval vaulted space with associated cave-like cellars.
• Enoteca I Terzi: A wine bar offering an nice selection of Tuscan wines paired with traditional dishes

Shopping

As you stroll through Siena, you'll naturally encounter boutiques, bars, and souvenir shops. Via di Città, Via Banchi di Sopra, and Via Montanini are popular shopping streets. Look out for authentic Sienese ceramics, local wines, and handmade artworks as unique souvenirs.

Markets: Every Wednesday, the weekly market takes place at the Fortezza, and once a month, the antique market is held at Piazza del Mercato.

Events

Here are some of the key events happening in Siena:

The Palio di Siena

Catch the thrill of the fierce horse race in Piazza del Campo, where the districts of Siena clash in tradition.
The Palio lasts four days: from 29 June - 2 July for the race of Provenzano and from 13 - 16 August for the race of the Assumption. Since the events are well known, you need to book your accommodations and tickets way ahead of time.

Accademia Musicale Chigiana

Throughout the year, enjoy classical music performances, peaking with the Chigiana International Festival during the summer. The shows are spread across historic spots in Siena.

For Jazz lovers

Jazz fills the air in Siena in July and August.

Opera at Monteriggioni Castle

Opera buffs can indulge in Verdi and Puccini at this castle. Amazing location.

Treno Natura

From spring to fall you can ride a steam train through Siena’s countryside. It takes you through Val d'Arbia, Val d'Orcia, and La Crete.

Fun Facts about Siena

Hidden underground network

Everybody knows about the Palio di Siena, but have you ever heard of Siena's hidden network of medieval tunnels and its ancient aqueduct? The aqueduct dates back to the Middle Ages and is still in use today. The 27 kilometers-long net of galleries were crucial in providing water to this historically water-poor city. This also sheds new meaning to the significance to the Sienese population of the fountain Fonte Gaia at the main plaza. The Bottini and Siena’s fountains are more hidden gems to visit.

Palio di Siena

The city is famous for the Palio di Siena, a traditional medieval horse race held twice a year in the Piazza del Campo. It's not just a race but a deep-rooted local tradition, involving all the city's districts or "contradas," each represented by different animals and colors.

Planned to be the largest cathedral of its time...

Siena’s Cathedral, known for its stunning artworks by renowned artists like Donatello, Michelangelo, Lorenzo Ghiberti, Gian Lorenzo Bernini, and many more, was originally planned to be the largest church of its time. The plan was to turn the main nave (which is already very impressive) into a transept and build a new colossal nave. However, the project was left unfinished due to the plague.

More Fun Facts

• Siena's medieval streets are organized in a unique shell shape, reflecting the city's origin as a former Roman military colony.
• Home of the oldest bank: The city was once a significant banking center and is home to the world's oldest bank, Monte dei Paschi, established in 1472.
• Each of Siena’s 17 historic districts has its own museum, preserving the unique art and history of their respective areas.