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Siena is the embodiment of a medieval city. Strolling through the red-brown brick houses, alleys and the magnificent churches and museums of this city in Tuscany will leave you feeling like you stepped into an architectural time warp. And the surrounding area is just as captivating, with its picturesque fields, vineyards and villages.

This guide will take you through this ancient city, highlighting the places to visit and things to do to experience Siena fully.

1. PIAZZA DEL CAMPO

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The Piazza del Campo was built where three hilltop towns sloped together, aiming to have a neutral ground for celebrating civic and political holidays. In 1995, this historic center was declared a UNESCO World Heritage Site. It is home to several of Siena's most important monuments and buildings, including the palazzo pubblico (city hall), which houses the civic museum and the Torre del Mangia tower.

Today, the main square is famous globally for the Palio di Siena (horse race), which takes place twice a year, in August and July. The numerous restaurants and cages surrounding the square offer a cozy spot for tourists to take a sightseeing break and enjoy the magic of the Piazza del Campo and its surroundings.

2. THE GOTHIC CATHEDRAL OF SIENA

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If the Piazza del Campo is the city's civic center, then the Siena cathedral (duomo di Siena) is its spiritual one. The sight of the cathedral rising atop the city's hills with its ornate striped facade is genuinely one of the most spectacular sights in Siena.

Besides its splendid exterior, its rich interior and associated buildings, such as the cathedral museum and the baptistery, are also wondrous to explore. You will also admire the works of several masters, such as Michelangelo, Bernini, Donatello and Nicola Pisano. The 56 marble panels on the cathedral's floors that show scenes from the old testament are an interesting site.

3. CLIMB THE TOWER OF MANGIA

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At 88 meters, the elegant Torre del Mangia Tower is a must-see. It took 10 years to build and is among the tallest ancient towers in Italy. The tower was not built with climbing tourists in mind, the stairways are pretty narrow, and the trek to the top includes more than 300 steps. However, if you get to the top, you will be rewarded with stunning views of the city's architecture.

4. WATCH THE PALIO DI SIENA

The Palio is a historic horse race that is one of Siena's most important and exciting events. In this event, the city’s contrade (districts) challenge each other to a race in the Piazza del Campo. This tradition dates to 1633 and happens bi-annually in the summer months of July and August.

If you want to catch the race, visit Siena during the Palio, and remember to pack a hat, a drink and sunscreen. Although you may need to purchase tickets, the wooden tribunes or the homes encircling the square offer more comfortable lodging.

5. VISIT THE SANTA MARIA DELLA SCALA

Between the 12th and 18th centuries, the Santa Maria Della Scala (one of Europe's oldest civic hospitals) cared for abandoned children, the sick and passing pilgrims. With the income the hospital generated from its landholdings, it commissioned altarpieces and frescoes that you can view today.

Today, the hospital is a museum complex with four floors worth of exhibits and the National Archaeological Museum in the basement.

6. TAKE A DAY TRIP TO SAN GIMIGNANO

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San Gimignano is a small village located roughly midway between Siena and Florence. The trip takes approximately 40 minutes from Siena, making it an ideal option for an adventurous day trip. It is renowned for its medieval architecture, with several high towers that offer wonderful views of the surrounding countryside. It is dubbed 'The Manhattan of the Middle Ages' because of the many tall residential towers that were a status symbol for its families. At the height of its glory, this village had around 72 tower houses, though only 14 have survived.

Since 1990, San Gimignano has been recognized as a UNESCO World Heritage Site. Visitors will get the chance to take a step back in time and be immersed in its feudal atmosphere while enjoying local products such as white wine and saffron.

7. EXPLORE THE VAL D’ORCIA

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Val d'Orcia is a rural agricultural landscape stretching between the Grosseto and Siena provinces. This rich and majestic landscape is the star of the show, and it features medieval castles, beautiful olive groves and vineyards, ancient villages and enchanting farmhouses. There is so much to experience in this famous region: the hilltop town of Radicofani and its castle tower to the south, the medieval small city of Montalcino to the west, and lush vineyards that produce exquisite Brunello wines.

After exploring the area, you can catch a break and unwind in one of the hot springs in the area. The wealth of the Val d'Orcia is also in the high quality of the foods it produces. These include Pecorino cheese, authentic extra virgin olive oil, truffles, mushrooms and wines. A trip to this area will immerse you in an unforgettable experience of rich flavors, beautiful and haunting architecture and striking landscapes.

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