Siena: Yes, It’s Worth a Stop on Your Next Trip to Italy

Thinking of heading to Tuscany? Here’s why you should make a stop in Siena.

Italy certainly has no shortage of world-famous tourist destinations. It holds such beautiful cities as Rome, Venice, Florence, and many more. Siena is yet another great beauty in Italy’s crown. Once one of the most important cities of the European middle ages, this small city of roughly 50,000 still retains much of the architecture from its storied past. Though not quite as well known internationally as the major cities mentioned before, Siena is definitely one you will want to check out. Here are a few reasons why you should visit this dazzling medieval town.


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Palio di Siena, the famous horse race

The Palio

The life of Siena revolves around the famous annual horse race known as the Palio. 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, along with Spain’s San Fermin in Pamplona and Oktoberfest in Munich. If you want to be in town for this event though, be sure to book well in advance as the city will naturally be crowded. Consider staying at our favorite 4-star family-friendly hotel near Piazza del Campo.

Is Siena Worth Visiting? Aerial View of the town of Siena in Italy
Siena is set in the heart of Tuscany. Located between the famous Chianti wine region and the beautiful city of Florence.

The History

Historians believe that Siena dates back to the time of the Etruscans, an advanced but mysterious people who lived in central Italy before the Romans. Though its golden age would not come until the middle ages, the city still holds two thousand years and more of history. For much of its heyday, between 1125 and 1555, Siena was a wealthy and independent republic that often fought with its rival city of Florence until it was conquered by the Medici family. Despite being overshadowed by its rival, the city has still been the home of popes, artists, and leaders. Yet another interesting fact is that Siena is also home to the world’s oldest bank in operation, the Monte dei Paschi di Siena, founded in 1472.


RELATED: How To Spend 3 Days in Rome – What To Do, Where To Eat & Drink

Winetraveler Tip: Can’t get enough of Italy? Want to learn about other special Italian destinations? Take a look at a wide range of articles and travel guides related to Italy right here.


The Siena Cathedral in the Piazza del Duomo
The Siena Cathedral in the Piazza del Duomo at sunset.

The Art

Like so many old Italian cities, Siena is a treasure trove of great art. Though there are a few artifacts from the classical era, much of Siena’s art comes from the late middle ages. There are several important museums you can explore, including the Pinacoteca Nazionale, which holds the majority of the city’s astounding religious paintings. However, another great highlight is the city’s cathedral and attached museum. Here are arguably the greatest treasures the city has to offer, including some early works by famous names like Michelangelo, Bernini, and Donatello, not to mention the dazzling fresco cycle of the life of Siena native Pope Pius II, and the intricately carved naturalistic pulpit. Meanwhile, the adjacent museum holds a 14th-century altarpiece called the Maesta, which many argue is the masterwork of Duccio, Siena’s most famous local artist.

Inside the courtyard of the Palazzo Pubblico
Looking up inside the courtyard of the Palazzo Pubblico.

The Architecture

However, you don’t necessarily need to go inside any building to appreciate the beauty of this city. The urban fabric of the city itself is a work of art. Virtually every period of European architecture from the Romanesque to the 19th century can be found in Siena’s old center. We highly recommend taking a private walking tour of the city with a local guide. Find any street to walk down and you’ll be met with a feast for the eyes. If you want, you can visit one of the city’s great architectural highlights, the Palazzo Pubblico and climb up its 300 ft tall main tower to get a wonderful birds-eye view of the city and surrounding countryside. From there you can see just what a winding maze the city is. However, in exploring it you’re sure to find it’s a maze you don’t mind getting lost in.

Classic Pici Pasta done with Truffles in Siena
Siena’s classic Pici Pasta done with local truffles.

The Food

Just as in anywhere else in Italy, there’s plenty of great food to be found in Siena. Of course, there are plenty of shops selling world-famous Italian dishes like pizza or spaghetti with tomato sauce. However, the regional cuisine of Siena and Tuscany also has plenty of unique dishes to offer. As far as pasta goes, one of the most quintessentially Sienese dishes is pici, handmade long thick strands of pasta, in a sauce based on wild boars meat. For dessert, you could try another local delicacy, such as the delicious almond-based ricciarelli cookies. To wash it down there’s never a bottle of Chianti too far out of reach, as the region in which it’s produced lies just outside the city.


RECOMMENDED: Want an immersive and authentic foodie experience in Siena? Schedule a dinner with your loved one in the middle of a vineyard, or book a Brunello di Montalcino wine tasting day trip from Siena.

While there are many more details that could be added as to why Siena is a world-class place to visit, the ones written here should be more than enough to show you why you’ll want to mark it down as one of your top spots to visit when in Italy.

More Italian Travel Guides and Travel Inspiration

Discover Central Italy: A Wine & Food Lover’s Travel Guide

Chianti Itinerary: How To Spend 5 Days in Italy’s Chianti Region

10 Charming Italian Towns To Visit if You Love Food and Wine

San Marino 2 Day Itinerary: Complete Travel Guide

Here’s Why You Should Visit Ischia Italy: Europe’s Best-Kept Island Secret

Cinque Terre Italy Itinerary: Travel Guide For Wine Lovers


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ABOUT THE AUTHOR

Greig Santos-Buch is a Co-Founder at Winetraveler, WSET II Merit wine thought-provoker and off-the-beaten-path outdoorsman. He first became involved with wine traveling after a month-long solo trip to Spain about 10 years ago, planning the trip almost exclusively around the gastronomic scene of the country. Ever since that particular trip abroad, he developed a passion for traveling and making wine tourism the core driver behind where he ends up. This has since led him to exciting destinations including the Czech Republic, to Austria, Germany, Switzerland, France, Italy, Portugal, California, Washington State, Canada and beyond. His primary aim through Winetraveler is to expose this style of travel to the world and make it accessible to everyone.

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