Top Siena Tours by Duration in 2026

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

Just 2 km from the old town of medieval Siena, in the stunning hilly Tuscan countryside, the exclusive wine tour with tasting ‘Land, Climate and Taste’ will introduce you to the local food and wine and to the fascinating world of sustainable wines. A journey through the secrets of viticulture in the age of climate change. Designed for all those who love fine wine and food, this intimate experience is for a maximum of 8 people and is led by one of the winery's owners. The winery tour will be followed by a guided sensory tasting session to capture and break down the different organoleptic profiles that participate in the complexity of our vintage and private reserve wines. Finally, you will enjoy a full lunch with the right food and wine pairings that will delight your palate and nourish your soul.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

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.

Hop on a full-day private tour to Florence and San Gimignano from Siena. Your adventure kicks off with a drive from Siena to Florence to explore the city center. Take a guided walking tour of the historic center and see key landmarks, including the Duomo, the Uffizi Gallery, and the Ponte Vecchio. Then, it's off to experience the medieval town of San Gimignano, known as the "medieval Manhattan."

Get views you can't find anywhere else on this hot-air balloon ride over Tuscany. Starting in Siena, float above the countryside and take in scenic views of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) and enjoy seeing the countryside and surrounding ancient villages and towns. Upon landing, enjoy a glass of sparkling wine to celebrate your experience.

Siena has one of the most intact medieval cityscapes in Italy, and with this walking tour, you can take in the hill town’s top sights in just two hours. Skip the hassle of following a map and instead head straight to the highlights with a guide. Stroll past Piazza del Campo, the town hall, and the Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.

Enjoy a private tour of two of Montalcino’s most exclusive wineries, taste their award winning wines and visit their winemaking facilities. Our native English speaking guide will be with you throughout your unforgettable experience and will take you to lunch at one of the regions top restaurants.

See Tuscany in classic Italian style by exploring the bucolic region in a vintage Fiat 500. Take the wheel of the classic Italian automobile then ride to the stunning hilltop town of Monteriggioni, cruise through the rolling hills of Chianti, and stop at a local vineyard for a hearty lunch of local fare.

The audio guide is a convenient mobile companion for a self-guided walk in Siena. The tour is designed specifically for getting to know the city in a relatively short time of 1.5–2 hours. Follow the route on the in-app map to walk from Piazza del Campo to the Medici Fortress, passing by the city’s main landmarks. Highlights include: Siena Cathedral, Fonte Gaia, Palazzo Chigi-Saracini, Galluzzi Arches, Fontebranda Fountain, House of Saint Catherine of Siena. The tour includes 26 points of interest. All stories are written by professional journalists and historians with a touch of humor and a love of travel. After you download the tour, you can run it offline in the app. We recommend using headphones to hear the audio guide clearly. Enjoy engaging stories and legends as you move at your own pace, without the need to follow a tour group. At any moment, you can stop to rest at a café or turn into a picturesque alley, and then continue your walk around the city.

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.

Tuscany is known for its excellent vintages, but the world of Tuscan wine can be overwhelming for a novice. With this informal wine class, you’ll get your bearings and learn to recognize the most important and storied wines of Tuscany. Delve into the history of Tuscany’s wine production, discover the different wine-producing areas and grapes, and sample a number of reds and whites from the region.

Cycle at your own pace with a local English-speaking guide who can tell you about the area. Admire the famous Val d’Orcia area close up, stopping when you want for photos. Enjoy a coffee in Pienza the main town on top of the valley, just like the local cyclists do.

Have a special night in Chianti's vineyards, enjoying dinner under the stars. Visit the farm's wineries for wine tastings, and savor local dishes in a cozy setting with candles. Have a BBQ with fresh farm food and taste Chianti's red wine. Allow the warmth of the barbecue, the fragrances in the air, and the essence of the grapevines to elevate your dining experience. The charming rural setting ensures a relaxing evening in the vineyards located in the stunning Chianti region.

Discover the Siena of the soul during the Jubilee with a local guide expert in religious itineraries. The tour includes the following itinerary: Native places and history of the life of Saint Catherine, patron saint of Italy and Europe, you will visit San Domenico where his relics are preserved, the birthplace and the famous chapel where he received the Stigmata in front of a wonderful wooden crucifix. We will talk about Saint Bernardino of Siena, and we will see the exact point from which he preached to the Sienese in Piazza del Campo where the tile of the exact point is still visible. You will visit the splendid Basilica of San Francesco which preserves one of the most important Eucharistic Miracles in the world, namely the miracle of the Sacred Uncorrupted Particles. We will talk about the famous Blessed Ambrogio Sansedoni and San Bernardo Tolomei who founded the monastery of Monte Oliveto. At the end you will have a rich tasting of local products in a typical place, cold cuts-cheeses-oil-wine to also restore the body, after the spirit.

Avoid the challenge of navigating Tuscany’s rural roads and finding hidden countryside trails on your own with a guided horseback ride from Siena. This gentle journey carries you through rolling hills, vineyards, and olive groves, reaching quiet landscapes that cars can’t access. Ride at a relaxed pace while taking in the region’s natural beauty and rural charm without any planning or navigation stress.

Exploring Siena with kids has never been so much fun! Your kid-friendly guide will introduce your family to Saint Catherine of Siena—one of Italy’s most important saints—with tales that spark imagination and curiosity. Then, make your way through the city’s narrow streets toward Piazza del Campo, where the legendary Palio horse race takes place, and your guide will share the thrilling traditions, pageantry, and playful rivalries. Nearby, you’ll discover Fontebranda, one of the oldest fountains in the city, and you’ll pause outside the Torre del Mangia. Even without climbing it, this tall bell tower inspires awe—and laughter—when kids learn the funny origin of its name. The tour concludes with a visit inside the magnificent Siena Cathedral. Its bold black-and-white marble stripes, intricate floors, and awe-inspiring sculptures are the perfect finale to your family’s journey. This family-friendly tour is a wonderful way to experience Siena’s beauty, history, and legends together.

Experience the flavors of Tuscany with a hands-on cooking class set on a charming farm in the Chianti countryside. Begin your experience with a guided lesson led by a professional chef, who will introduce you to traditional Tuscan recipes and techniques. Using fresh, local ingredients, you’ll prepare a selection of classic Italian dishes, including homemade pasta and flavorful sauces, learning step by step how to recreate them. After the cooking session, relax and enjoy a guided wine tasting featuring a selection of regional wines, including IGT, Chianti, and Chianti Classico. Discover the characteristics of each wine and the traditions behind their production, while pairing them with local specialties such as bruschetta and salami. Finally, sit down to enjoy the meal you’ve prepared, accompanied by Tuscan wines in a welcoming countryside setting.

With no train station and spotty bus service, San Gimignano can be a hassle to reach from Siena. On this small-group tour, sip world-class wine and watch the sunset over Chianti and San Gimignano with stress-free transportation. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills.

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

Many of Italy’s most charming hill towns are a challenge to reach with public transport. This private day trip offers seamless round-trip transport, giving you time to explore Volterra and San Gimignano at your own pace. Enjoy free time in both towns, with lunch at a Chianti cellar accompanied by a tasting of five different wines.

Explore Quaint Villages and Timeless Landscapes Our journey will take you off the beaten path, winding through both lesser-known hamlets and iconic landmarks alike. Immerse yourself in the rich history and culture of each village we visit, from hidden gems tucked away in the countryside to well-known destinations steeped in tradition. Capture Every Moment, Embrace Every View As we traverse the rolling hills and winding roads, there will be ample opportunities to pause and soak in the panoramic views. Experience the Joy of Open-Air Travel Feel the sun on your face as you cruise through the Val d'Orcia on your Vespa. This isn't just a tour – it's an immersive journey into the heart of Tuscany's natural beauty. Let the open road be your guide as you embrace the freedom of outdoor exploration. Don't Miss Out on This Unforgettable Experience Join us for a Vespa adventure like no other and discover the magic of Val d'Orcia in a whole new way.

Discover the beauty of Siena on a private walking tour through its most iconic landmarks, where medieval charm, art, and spirituality blend in perfect harmony. Your journey begins at Piazza San Domenico, closely tied to the life of St. Catherine, Siena’s patron saint. Just a short stroll away lies the Santuario Casa di Santa Caterina, a peaceful complex built around the birthplace of the saint. Nearby, you’ll come to Fontebranda, one of Siena’s oldest fountains. Your walk continues into the beating heart of the city: Piazza del Campo, a breathtaking shell-shaped square often considered one of Europe’s finest. Lined with graceful palaces and crowned by the Palazzo Pubblico and the Torre del Mangia, this is the stage for the world-famous Palio horse race. No visit to Siena would be complete without exploring the Duomo, a Gothic masterpiece adorned with black-and-white marble stripes, richly decorated interiors, and priceless works of art by masters such as Michelangelo.