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Jane's Guide to Siena

Siena is a medieval city in Tuscany with a UNESCO-listed historic center. Surrounded by a well-preserved 1,000-year-old wall, it's best known for hosting the Palio horse race in the iconic Piazza del Campo. Siena has over two thousand years of history, but it’s most prosperous time was between 1125 and 1555 when it was an independent republic. Siena is often overshadowed by its rival city of Florence. In fact the two cities fought each other often until Siena was finally conquered by the Medici Family, but Siena was also once the home of many popes, painters and artists.

Where to stay in Siena

Rent your own apartment to feel like a local in Siena.

Or stay in Hotel Santa Caterina and enjoy their patio with a view at the end of your sightseeing day.

If you’re touring Italy by car, you might stay outside of Siena and enjoy a swimming pool.

What to do in Siena

Hang out for a while in Piazza del Campo. The shell-shaped square in the city center of Siena is the heart of Siena and like all roads lead to Rome, all the cozy narrow streets in Siena lead to this bowl-shaped square. In the square you will find the Fonte Gaia, a monumental fountain that leads the water from the hills north of Siena to the Piazza. The formed underground channels are called bottini and they serve all the fountains in Siena. When the water first reached the piazza in 1342, a feast was held full of joy. That is why the fountain is named after this: Fonte Gaia means source of joy. Grab a table around the square and have a coffee, a glass of wine or an aperol Spritz to enjoy soaking up the atmosphere of the piazza.

Visit the Duomo. The construction of the Cattedrale di Santa Maria Assunta started in the twelfth century. It is one of the best known examples of Italian Gothic architecture. In addition to the distinctive black and white striped exterior, the cathedral's façade, built in 1380, is richly decorated. Next to the cathedral is the 252 ft high campanile, the freestanding bell tower. You can also add on a visit to the cathedral’s museum across the street, Santa Maria Della Scala Museum.

Climb to the top of the Torre del Mangia. Go all the way to the top of the 335 ft tower in the center of Siena for some of the best views in Tuscany. It’s worth every step! Built in the fourteenth century by the Rinaldo brothers, it stands next to the Palazzo Pubblico. At the foot of the tower, there is a chapel that was added after the plague in 1352.

Visit Siena’s patron saint, Catherine of Siena at the Basilica Cateriniana di San Domenico. The Gothic style San Domenico is a large church from the fifteenth century. It was built by the Dominicans in honor of Saint Domenicus, and then Catherine of Siena was laid to rest here in 1380 in a chapel dedicated to her. Artist Sodorna also has several frescoes dedicated to Catherine.

Combine history and wine-tasting with a visit to the Fortezza Medicea, a fortress built especially for Cosimo de Medici. Today, the red-brick fortress houses a well-known Enoteca, where you can taste different wines from the region.

Go to market day if you are in town on a Wednesday. Visit Siena’s weekly outdoor market at La Lizza. From 8.30 to 13.30, the market stalls and vendors fill the streets around the fortress.

Plan to be in Siena for the Palio Horse Race. Every second of July, the seventeen neighborhoods of Siena, called contrades, all hire a horse and jockey to meet up in the city’s central plaza and race. The winning contrade is honored in the city’s cathedral. Featured in numerous feature films, the Palio is one of the most well-known festivals in Europe.

Where to eat in Siena

The best restaurant in Siena might be Ristorante Campo Cedro. The food is gorgeous as well as delicious. Book ahead and go for the tasting menu. Dietary restrictions can be honored on request, and they do an excellent job with wine pairings.

For well-loved, traditional Sienese food, you can’t go wrong with Osteria La Sosta di Violante. Be sure to book ahead as they stay busy. Order the lasagna if you haven’t had it in Italy before, or they also do a great steak.

Casato Ristorante Wine Bar is a great find just off the main square where you can duck away from the crowd to fill up on a delectable sea urchin pasta or just sit and have a glass of wine.

For pizza, head over to Pizzeria Alle Scalette. The margarita is the favorite, but the choices are endless.

Siena is famous for ricciarelli, a special chewy almond cookie. Stop into one of Siena’s gorgeous pastry shops to try one! I recommend Pasticceria Nannini Conca D'Oro.

How to get to Siena

There is a train station just outside the old town center of Siena with direct connections to Rome and Florence. The distance from the station to the center of town is walkable, but if you have a lot of luggage you can grab a taxi or hop on a bus just outside the station.


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