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

By | Travel & Wine Writer, Co-Founder
Last Updated: October 20, 2023
Reasons why Siena is Worth Visiting and what the town is known for.

Thinking of heading to Tuscany? Here’s why you should visit 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.

Top Reasons to Visit Siena Italy

The Palio

Palio di Siena Horse Race Start at the Mossa
Jockeys and horses burst into action at the Mossa, Piazza del Campo, during the vibrant Palio di Siena, Italy’s historic and fiercely competitive bareback horse race.

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.

The History

Aerial view of Siena
Siena is set in the heart of Tuscany. Located between the famous Chianti wine region and the beautiful city of Florence.

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 Art

Elevated view of the nave inside Siena's Cathedral in Italy
The mesmerizing nave of Siena Cathedral (Duomo di Siena) invites travelers to marvel at its soaring Gothic arches, intricate frescoes, and intricate inlaid marble floors, creating an enchanting atmosphere that sparks wonder and reflection.”

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.

The Architecture

Courtyard of Palazzo Pubblico in Siena
Looking up inside the courtyard of the Palazzo Pubblico.

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.

The Food

Food in Siena Italy: Pici Pasta
One of Siena’s classic dishes, Pici Pasta topped with local truffles.

Siena, like the rest of Italy, is a haven for food lovers, offering a delightful array of both traditional Italian dishes and unique regional specialties that showcase the flavors of Tuscany. Alongside the familiar pizzas and spaghetti dishes, visitors to Siena can discover a wealth of culinary treasures that reflect the city’s rich heritage and local ingredients.

The rustic pasta dish, pici, is a prime example of Siena’s distinctive cuisine. These thick, hand-rolled strands of pasta are traditionally served with a hearty sauce, such as a savory wild boar ragù, that highlights the flavors of the region’s game. Another notable Sienese pasta dish is panzarella, a bread and tomato salad that makes use of stale bread, tomatoes, onions, and basil, all tossed in a simple vinaigrette.

In addition to pici, Siena is known for its mouthwatering array of main courses. One such dish is ribollita, a robust bread and vegetable soup that showcases the region’s abundant produce. For meat lovers, bistecca alla Fiorentina, a thick, succulent T-bone steak grilled to perfection and seasoned with salt, pepper, and a drizzle of olive oil, is a must-try.

As for dessert, Siena offers a variety of sweet treats that are sure to delight. Ricciarelli, almond-based cookies with a soft, chewy texture, are a local favorite, while panforte, a dense, spiced fruitcake packed with nuts and dried fruit, is another traditional Sienese confection. Cantucci, crunchy almond biscuits often dipped in the sweet dessert wine Vin Santo, provide a fitting end to any meal.

Siena’s gastronomic scene is further enhanced by its proximity to the Chianti wine region, ensuring that a fine bottle of this renowned red wine is always within easy reach. As travelers explore Siena’s culinary landscape, they will find a rich tapestry of flavors and dishes that both surprise and delight, revealing the city’s unique character and deep-rooted traditions.

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.

Proximity to Renowned Italian Wine Regions

View from the walls of Montepulciano not far from Siena
From the walls of Montepulciano not far from Siena: A panoramic embrace of Tuscany’s enchanting landscape, where rolling hills and lush vineyards converge in a harmony of nature’s vibrant colors.

Siena provides an idyllic starting point for wine enthusiasts eager to explore Italy’s renowned wine regions. Its central location and excellent transportation connections make it easy to venture out and discover the picturesque vineyards, historic wineries, and world-class wines that these regions have to offer.

Chianti, perhaps the most famous of Tuscany’s wine regions, is a short drive from Siena. This area is known for its rolling hills, lush vineyards, and the production of Chianti Classico wines, which are primarily made from the Sangiovese grape. Visitors to Chianti can tour historic wineries, partake in guided tastings, and even participate in grape harvest experiences during the season. Moreover, the region boasts several small towns and villages, such as Greve in Chianti and Radda in Chianti, which add to the overall charm and appeal.

Montalcino, another prominent wine region, is located to the south of Siena. This area is famous for producing Brunello di Montalcino, a high-quality red wine made exclusively from the Sangiovese grape. Montalcino offers wine travelers the opportunity to visit distinguished wineries and learn about the meticulous winemaking process that goes into crafting these exceptional wines. In addition, Montalcino’s historic town center, with its fortress and cobblestone streets, provides a delightful setting for a leisurely stroll or an alfresco lunch.

Montepulciano, situated southeast of Siena, is yet another alluring destination for wine enthusiasts. The region is celebrated for its Vino Nobile di Montepulciano, a full-bodied red wine primarily made from the Prugnolo Gentile grape, a clone of Sangiovese. Visitors can wander through Montepulciano’s enchanting town center, characterized by its Renaissance architecture, and explore its underground cellars, where the aging of Vino Nobile takes place. The town also hosts the annual “Bravìo delle Botti,” a barrel-rolling competition that celebrates the region’s wine heritage.

Apart from these famous wine regions, Siena’s proximity to lesser-known yet equally captivating areas, such as Bolgheri, San Gimignano, and Maremma, allows wine travelers to expand their horizons and discover a diverse range of Italian wines.

Wine Festivals

Wine festivals in Siena provide a unique and enjoyable way for visitors to immerse themselves in the local wine culture and traditions. Throughout the year, the city hosts several events that attract wine enthusiasts from around the world, eager to explore the diverse range of local wines and connect with winemakers who passionately share their knowledge and expertise. These festivals often feature tastings, seminars, workshops, and live entertainment, all set against the picturesque backdrop of Siena’s historic city center.

One of Siena’s prominent wine events is the Siena Wine Fair (Enologica Montecchio), which takes place annually and showcases a variety of local and regional wines. This event offers attendees the chance to sample wines from various Tuscan appellations, as well as to engage with winemakers and industry professionals in a relaxed and convivial atmosphere. Similarly, the Chianti Classico Wine Festival celebrates the famed Chianti Classico wines, inviting visitors to learn about the unique terroir and winemaking techniques that contribute to the distinct character of these wines.

Archeological Sites

The wealth of archeological sites around Siena allows travelers to delve into the region’s ancient past and gain an appreciation for the rich history that has shaped the area over the centuries. One such site is the Etruscan Necropolis of Poggio Civitate, nestled near the quaint town of Murlo. This impressive archeological complex, dating back to the 7th century BCE, offers visitors the chance to explore well-preserved tombs and examine artifacts that provide a window into the lives and customs of the ancient Etruscan civilization. The site also features an archeological museum, where visitors can view exhibits showcasing pottery, jewelry, and other fascinating items unearthed during excavations.

Just a short drive from Siena, travelers can also discover the Roman theater in Fiesole, which provides a fascinating insight into the region’s Roman history. This ancient theater, built around the 1st century BCE, was once capable of accommodating up to 3,000 spectators and still retains its original stone seating and stage. Today, the theater serves as a stunning backdrop for various cultural events, including concerts and performances, allowing visitors to experience the site as it might have been during its heyday.

Outdoor Activities

The enchanting landscapes around Siena beckon adventure seekers and nature lovers alike with their breathtaking beauty and abundant opportunities for outdoor activities. Hiking and biking trails wind their way through the picturesque countryside, allowing travelers to immerse themselves in the tranquil ambiance of Tuscany. As you traverse these scenic paths, admire the lush vineyards, verdant olive groves, and stately cypress-lined hills that have inspired artists and poets for centuries. These trails cater to various skill levels, from leisurely strolls through the idyllic landscape to more challenging treks that reward hikers with panoramic views of the region.

For those seeking a truly unforgettable experience, book a hot air balloon ride for an unparalleled vantage point from which to appreciate the stunning Tuscan scenery. As the balloon gently ascends, riders are treated to a bird’s-eye view of the charming villages, rolling hills, and historic castles that dot the landscape. Floating above the picturesque terrain, marvel at the vibrant patchwork of vineyards, fields, and forests that stretch as far as the eye can see. This exhilarating activity not only creates lasting memories but also provides a unique perspective on the beauty and allure of the region surrounding 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.

Val d’Orcia

Val d'Orcia in the Siena Province
Discover the essence of Tuscany in Val d’Orcia: a captivating panorama of undulating hills, golden vineyards, and gracefully winding cypress-lined paths, revealing Italy’s timeless charm.

The Val d’Orcia, a UNESCO World Heritage Site designated in 2004, is a stunning valley located in the province of Siena. Situated to the south of the city, this picturesque area is renowned for its captivating landscapes, characterized by rolling hills, cypress-lined roads, and verdant vineyards. The region’s natural beauty has inspired countless artists, poets, and photographers over the centuries, with its iconic scenery often regarded as the quintessential representation of the Tuscan countryside. In addition to its breathtaking vistas, the Val d’Orcia is home to several charming hilltop towns, such as Montalcino, Pienza, and San Quirico d’Orcia, each boasting their own unique history and architectural treasures.

Travelers exploring the Val d’Orcia will be captivated by the harmonious blend of nature, culture, and history that imbues the region with a singular charm. The area offers numerous opportunities for leisurely walks, hikes, and bike rides through its enchanting countryside, allowing visitors to immerse themselves in the tranquil ambiance and awe-inspiring landscapes. Moreover, the Val d’Orcia is known for its exceptional food and wine, with the region producing some of Italy’s most acclaimed wines, such as Brunello di Montalcino and Vino Nobile di Montepulciano. Culinary enthusiasts will relish the chance to sample the area’s delectable cuisine, which showcases the freshest local ingredients and time-honored recipes. In essence, the Val d’Orcia provides an unforgettable travel experience that appeals to all the senses, leaving visitors with a profound appreciation for the natural and cultural wonders of Tuscany.

How to Get to Siena

To reach Siena, travelers have several options, with the nearest airports being Florence Airport (FLR), Pisa International Airport (PSA), and Bologna Guglielmo Marconi Airport (BLQ). Florence Airport, approximately 85 km (53 miles) from Siena, is the closest and most convenient option. Check flight deals to any of these airports from your origination point right here.

Upon arrival at the airport, self-guided travelers can rent a car and drive to Siena, which takes around 1 hour and 15 minutes from Florence Airport, 2 hours from Pisa International Airport, and about 2 hours and 30 minutes from Bologna Guglielmo Marconi Airport. Italian highways are well-maintained, and driving allows for flexibility and the opportunity to explore the scenic Tuscan countryside at your own pace.

Alternatively, public transportation is available from each airport. From Florence Airport, take a shuttle bus or taxi to Florence’s Santa Maria Novella train station, and then board a train to Siena, which takes approximately 1.5 hours. From Pisa International Airport, there is a direct train to Siena, with a travel time of around 2 hours. From Bologna Guglielmo Marconi Airport, take a shuttle bus or taxi to Bologna’s main train station, and then board a train to Siena, which takes about 2 to 3 hours, depending on the connection.

For those who prefer guided options, several tour operators offer private transfers and organized group tours from the airports to Siena, allowing you to sit back and enjoy the journey without the hassle of navigating on your own.

Guided Tours of Siena and Private Transfers

Guided tours and transfers offer a convenient and enjoyable way to explore Siena, providing Winetravelers with a stress-free and immersive experience. Opting for these services ensures that all transportation logistics are taken care of, allowing yourself time to relax and enjoy the journey without worrying about navigation, driving in a foreign country, or dealing with public transportation schedules. This option is particularly beneficial for those with limited time or unfamiliar with the Italian language. Additionally, experienced tour guides possess extensive local knowledge, which can enrich your visit by providing a deeper understanding of Siena’s history, culture, and hidden gems. They can also offer recommendations on the best places to eat, shop, or explore, ensuring a memorable experience.

Private Transfer to Siena

Experience a comfortable and stress-free journey from Florence to Siena in a private, modern, air-conditioned vehicle, driven by a professional chauffeur. This transfer is operated by Ciaoflorence, one of our favorites and trusted in the region.

Your driver will meet you at your accommodation or the airport in Florence, and whisk you away on a safe and comfortable 1-hour trip to Siena in a luxurious Mercedes vehicle. As you travel, sit back, unwind, and take in the breathtaking Tuscan landscape.

With drivers hand-picked for their local knowledge, feel free to seek tips or advice on what to do during your Siena stay. The private transfer service is available 24/7, ensuring your transportation needs are met at any time. For air travelers, rest assured that your driver will monitor your flight’s progress, guaranteeing a seamless journey to Siena, even in the event of delays.

Siena Guided City Tour with Cathedral Skip-the-Line Entry

Discover the enchanting city of Siena on a small group or private walking tour, guided by an expert who will reveal its famous landmarks and hidden gems. Enjoy the convenience of pre-reserved tickets to the magnificent Siena Cathedral.

Begin at the Gothic San Domenico Basilica, then meander through winding paths offering panoramic views of the city, including the Duomo and Torre del Mangia. Learn about Siena’s medieval history and admire the area’s oldest palaces. Pause to appreciate the charm of the UNESCO-listed, seashell-shaped Piazza del Campo and the captivating Fonte Gaia fountain.

Delve into the history of Siena’s contrade (districts) and their biannual rivalry during the Palio horse race. Immerse yourself in the authentic atmosphere of a typical contrada, and visit a local pastry shop, renowned for its traditional Ricciarelli and Panforte made from age-old recipes.

With pre-reserved tickets, explore the awe-inspiring Siena Cathedral, marveling at the intricate marble mosaic floor, stained glass, and medieval masterpieces by Duccio and Pisano. Witness the Renaissance highlights, including sculptures by Donatello, Michelangelo, and Bernini, and Pinturicchio’s frescoes in the Libreria Piccolomini. Conclude your tour, rich with newfound knowledge, in the square before the cathedral.

From Florence: Day Trip to Pisa, Siena & San Gimignano with Lunch

Embark on a 12-hour adventure through Siena, departing from Florence to explore the region’s captivating landscapes, architecture, and art. Indulge in local cuisine and join a guided tour to delve deeper into the area’s rich history.

Begin in Siena’s Piazza del Campo, known for the thrilling Palio di Siena horse race, and marvel at the impressive cathedral in Piazza del Duomo. After some leisure time, savor lunch at a traditional Tuscan winery before visiting the vineyard to sample local wines. Next, explore the UNESCO-listed medieval town of San Gimignano, famous for its Vernaccia di San Gimignano wine and picturesque tower-filled skyline.

Conclude your journey in Pisa, where the striking Piazza dei Miracoli awaits. Admire the Baptistery, the Santa Maria Assunta cathedral, and the iconic Leaning Tower of Pisa, rounding off a day filled with unforgettable Tuscan experiences.

Tuscan Cooking Class in Central Siena

Immerse yourself in the culinary traditions of Italy with a hands-on Tuscan cooking class in Siena. Under the expert guidance of a professional chef, learn to prepare a variety of authentic Italian dishes, from homemade pasta to succulent cuts of meat. This intimate experience, held in a professional kitchen, is limited to a small group of 15 participants or fewer to ensure personalized attention.

During this delightful Tuscan cooking class, you’ll work with fresh, locally-sourced ingredients to create a delectable meal. A vegetarian option is available to accommodate all preferences. At the conclusion of the class, gather with your fellow food enthusiasts to savor the fruits of your labor, expertly paired with exquisite wines to enhance the flavors of your creations.

Walking Tour of Siena with Food & Chianti Wine

Take a captivating tour of Siena operated by Moro Tuscany Travel, guided by a local who will share insights beyond what guidebooks offer. Join a small group limited to just ten people, ensuring an intimate experience as you explore the city on foot. Delve into the history behind the UNESCO-listed Piazza del Campo and its surrounding monuments, while uncovering lesser-known stories and secrets of Siena.

By booking your Siena walking tour with tastings online, you can secure your preferred date and enhance your exploration with a local’s perspective. Discover the best vantage points for capturing stunning photos of the city as you traverse its charming streets. Gain a deeper understanding of Siena’s medieval history and architecture, and savor the flavors of classic Tuscan cuisine, accompanied by delectable Chianti wine.

Small Group Brunello di Montalcino Wine Tasting Trip from Siena

This delightful day trip from Siena allows you to explore the exquisite wine region of Brunello di Montalcino, renowned for producing one of Italy’s finest wines. In a small, intimate group of no more than eight people, venture beyond Siena and immerse yourself in the enchanting world of winemaking.

Led by an expert guide, visit the cellars to uncover the secrets behind the production process and meet the passionate locals responsible for crafting the exceptional red wine. Enjoy tastings at three different wineries, and savor a delectable Tuscan lunch at a family-run estate.

Beyond the wineries, stroll through the picturesque village of Montalcino and marvel at the mystical Abbey of Sant’Antimo. With additional tastings along the way, this small-group tour offers a truly intimate and unforgettable experience, culminating in a leisurely return to Siena. This day trip is one of the most highly-rated in the area and sells out quickly, so be sure to book well in advance.

Book Activities & Things to Do in Siena Online

Frequently Asked Questions about Visiting Siena

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

You are reading “Reasons to Include Siena on Your Trip To Italy ” Back To Top

how to visit Tuscany, best places to visit in Italy: top things to do in Florence

If you enjoyed this guide, consider joining the Facebook Group to interact with other Winetravelers and for travel inspiration around the world, and be sure to follow along with us on Instagram.

Get Articles Like These Directly in Your Inbox!

Subscribe to Winetraveler and receive notifications when new travel guides and itineraries are published. It's free!

Leave a Comment, Ask a Question or Share a Review

Share to...