Top Siena Walking Tours

Indulge in one of Italy's most beautiful cities, Siena, during this sightseeing tour. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every July and August. Stroll the streets with your guide learning about the history of the place. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket. 

Maximize time in Siena with a guided walking tour through the medieval city streets. See local landmarks including Piazza del Campo and the Siena Cathedral while hearing stories about the city’s history and architecture from a local guide. Explore a local district, called a Contrada, and learn about Siena’s famous Palio horse races.

Discover the treasures of one of the most beautiful cities in the world with a monolingual local guide and immerse yourself in its art, culture and traditions as the horse race the Palio, which takes place twice a year. With a small group you will explore the best that Siena has to offer. Your guide will accompany you along the ancient streets of Siena through the most beautiful sites such as: Piazza del Campo, Palazzo Pubblico, Palazzo Tolomei, Palazzo Salimbeni, the ancient via Banchi di Sopra, the Basilica of San Domenico, the Sanctuary of St. Catherine of Siena, the Baptistery and the Cathedral. You will visit also the inside of the Cathedral (ticket not included), if you choose the Cathedral option, where you will admire the works of art of important Italian artists, such as Michelangelo, Donatello and Bernini.

Siena is a treasure trove of historical, artistic, religious and cultural riches all to be discovered. The best way to do it is on foot, admiring the changes to the town over the centuries and enjoying the spectacular scenery and curious particulars. With an authorized guide you will be able to appreciate the major tourist attractions like Piazza del Campo, the true heart of the town, the Palazzo Comunale (Town Hall), the Cathedral and the majestic Basilica of San Domenico. There will also be no lack of references to the great noble families, such as the Piccolomini, Tolomei and Salimbeni, and their palazzos, to the great tradition of the Siena Palio, but also to the stories of pilgrimage and saintliness that distinguish the town. The walk continues with a visit to the Cathedral that preserves the treasures of artists like Nicola Pisano, Duccio di Buoninsegna, Donatello and Gianlorenzo Bernini, besides its marvelous marble floor, which is a unique example in the history of art.

Stroll the charming Medieval streets of a Tuscan hill town with this 2-hour private tour of Siena. Learn about Siena's hidden gems from a knowledgeable guide in between visits to its most popular sights.

The magnificent Duomo of Siena is one of the highlights of Siena’s UNESCO-listed historic center, but its popularity means that you could spend a long time queuing outside. This skip-the-line ticket ensures priority entrance and offers access to the Cathedral, the Piccolomini Library, the Baptistery of San Giovanni, the museum, and the Crypt.

Visit San Gimignano, Monteriggioni, and Montalcino on a day trip from Siena, and discover medieval architecture, wine, and stunning views of Tuscany. With ample free time in each of the hill towns, the tour also includes lunch at a Monteriggioni winery plus samples of Chianti and Brunello di Montalcino wine.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this day trip from Siena. Led by an expert guide, travel to the cellars to learn about the production process and meet the locals behind the delicious red wine. Then, pause at a family-run winery for an authentic Tuscan lunch before exploring the village of Montalcino and the abbey of Sant'Antimo. Stop for additional tastings along the way and conclude with transportation back to Siena. Group size is reserved to eight people for a more intimate experience.

Take the stress out of planning a day in Tuscany on this half-day small-group tour of the Chianti wine region from Siena, including transport. Enjoy an air-conditioned ride over to two popular wineries to taste wines and oils locals love. Plus spend some free time in Monteriggioni, and catch a glimpse of the town’s well-known medieval castle.

Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Led by a local guide, admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with an optional visit to a winery. Group size is limited to eight people, ensuring personalized attention from your guide.

Get medieval on this guided tour from Sienna to San Gimignano and Volterra. Head to the marvelously diminutive hilltop town of Monteriggioni and then stop for a while in UNESCO world Heritage-listed San Gimignano with its plethora of medieval towers and commanding views over the Tuscan countryside. Finally, spend some time in an alabaster workshop in Volterra before indulging in a rustic lunch at a Tuscan farm. This small-group tour is limited to just eight people, ensuring plenty of personalized attention from the guide. 

Are you a curious and thirsty traveler looking to uncork some of Tuscany's wine secrets? Come to the Tuscan Wine School for an informative and fun class to learn about Tuscany's most important, traditional wines led by an English-speaking local expert. Discover the history and legends behind Tuscany's most significant wines and learn to swirl, smell and sip your way through the different types and styles of wine. The tasting of wines is enhanced by a series of different sample foods, and food pairing tips will be discussed, leaving you able to make better choices when choosing from local names in the city's restaurants.

Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.

Discover the medieval streets of Siena with a personal guide at your side, and find hidden-away corners far from the tourist crowds. Create a personalized itinerary on this private 3-hour tour, departing from Piazza del Campo in the morning or afternoon. Walk past major monuments as you explore on foot.

Tuscany is world-renowned for its wine, so ensure you get an insider’s glimpse into the industry during a tasting tour of the vineyards surrounding Siena. Receive personalized attention in a small group limited to 12 as you visit a historical cellar and educate your palate to recognize subtle flavors with the help of a sommelier. Plus, a choice of morning or afternoon departure means you can slot this tour into even the busiest of sightseeing schedules.

Spend an afternoon in the wine town of Montalcino, tasting the prestigious Brunello di Montalcino and learning about wine production. This tour from Siena that tasting of local wine paired with salami and cured meat. Admire views of the Tuscan countryside from the pretty hill town and discover the region’s generations-old winemaking traditions.

Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.

Discover the city’s historic city center by solving clues and unlocking stories on your phone. Play the engaging exploration game, reenacting the struggle of one of the most important families in Medieval Siena in their fight to gain power. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. And you can play offline. Ready for an adventure? Highlights include: • Admire the pretty fountain of Fonte Gaia, Piazza del Duomo, Palazzo Tolomei and many other local beauties. • Visit the second-oldest bank in the world. • Enjoy a uniquely crafted story brought to you by our talented writers. • Solve clues to find local stories and hidden gems as you explore. • Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt.

Learn all about Siena's famous horse race, the Palio, on this 1-hour, guided walking tour. Your guide shares all the details about the Palio's history and traditions of the race that takes place in the city square, the Piazza del Campo. Also visit one of Siena's 17 districts ("contrade"), whose representatives race in the Palio twice a year.

Siena is one of Tuscany’s most picturesque medieval towns and this private walking tour is ideal for first-time visitors or those short on time. Take in the highlights of the UNESCO-listed center, stroll around lively Piazza Del Campo, and admire landmarks such as San Domenico Basilica, Palazzo Tolomei, and Cathedral of Siena.

Our Polaguides will allow you to discover the most hidden places, but no less fascinating than Siena and instant photography will allow you to appreciate the beauty of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be personalized, to browse whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends.

Discover the flavors of Rome on a 2-hour food tour that highlights the best snacks in the city. Learn about the culinary scene in Rome as your guide takes you to small local eateries for samples of savory and sweet dishes such as pizza, gelato, and cannoli. You’ll also hear live commentary about historical and cultural highlights along the way.

If you are looking for a unique and fun activity to involve the whole family in the interactive discovery of the most hidden, but no less fascinating places in Siena, you cannot fail to try our Treasure Hunt! Furthermore, instant photography will allow you to appreciate the beauties of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be customized, to be browsed whenever you want. Find out all the details, solve the puzzles and answer the quizzes to transform your visit to Siena into a unique memory to share with the whole family, young and old, and with friends.

Ciao, I’m Alessandro, the owner of Siena Tartufi. I’m a truffle hunter from 20 years. I have 3 dogs, Moka and Freddie a Lagotto Romagnolo and Pepita, a black Labrador. I really love going outside with my dogs looking for truffles . In every season there are different types of truffle that will be collected and you can do it with us... My hobby is my job and my passion!