Siena, Tuscany Tours & Activities in 2026

Siena , Tuscany

From $ 46.54

Immerse yourself in Italy’s history on this 2-hour sightseeing tour. Explore Siena's UNESCO World Heritage-listed Old Town; discover Siena's central square, Piazza del Campo; and visit the stunning Siena Duomo (Siena Cathedral) with your fast-track, skip-the-line entrance ticket. As you walk through this incredibly beautiful Tuscan city with your expert guide, you'll feel as though you’ve journeyed back in time.

Siena , Tuscany

From $ 22.46

Single ticket for 3 hours for the wonders of the Cathedral of Siena, Piccolomini Library, Museum, Panoramic Terrace, Baptistery and Crypt. Amazing experience around the Gothic Town most famous of the world. The ticket will be valid for three consecutive days from first entry.

Siena , Tuscany

From $ 69.81

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.

Siena , Tuscany

From $ 84.94

Siena is one of Tuscany's best-loved cities, a fixed stop for those in the Chianti region. A destination for many visitors, Siena is internationally known not only for its picturesque, medieval historical centre, the famous Palio di Siena in Piazza del Campo and the colourful countryside that surrounds it, but also for the delicious cuisine it offers. It is impossible not to think of the excellent dishes and exquisite wines that can be found in the city. Thanks to our gastronomic tour of Siena, we will discover together the secret dishes and recipes of the Sienese tradition.

Siena , Tuscany

From $ 91.92

Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore the UNESCO historic center of San Gimignano at your own pace; step inside Monteriggioni’s perfectly preserved fortress. Follow the scenic Chiantigiana road to a cozy winery for a guided tasting of 3 Chianti wines and a zero-mile, 3-course lunch, finishing with cantucci & vin santo. Enjoy free time in Siena to wander Gothic lanes, browse artisan shops, and relax in lively enotecas. Quick stops at the striped Duomo and shell-shaped Piazza del Campo, home of the Palio. Ideal for travelers seeking art, wine, and views in one effortless day—round-trip transport and tour leader included. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

Siena , Tuscany

From $ 57.02

Visit two charming family-run wineries in the heart of the Chianti region, learn about local winemaking traditions, and taste 7 exquisite wines paired with bruschetta, salami, cheese, and extra virgin olive oil. Between tastings, stop at the medieval village of Monteriggioni for free time to explore or relax before returning comfortably to Siena.

Siena , Tuscany

From $ 69.81

Leave Siena behind and hike part of Via Francigena, an ancient pilgrimage route through rural Tuscany, followed by a wine tasting in the village of Monteriggioni. Embark on a 5-mile (8-km) trek that passes through the heart of the Tuscan countryside, past picturesque castles, villages, vineyards and ruins. Once you reach the medieval walled village of Monteriggioni, reward yourself during a wine tasting session, where you will sip on 3-4 different local, organic wines. Return to Siena at your own leisure by bus (bus tickets provided).

Siena , Tuscany

From $ 68.53

Enjoy an exclusive wine tasting combined with a typical Tuscan lunch in a medieval Castle in the heart of Montalcino.

Siena , Tuscany

From $ 86.10

Learn how to make pasta and tiramisu in a popular Siena restaurant. Enjoy a glass of Prosecco upon arrival, and a glass of wine with your meal.

Siena , Tuscany

From $ 32.58

The terrace, the white mulberry tree and the hills of Chianti Classico become part of your memory, a moment that will remain engraved in your soul. With each taste, your palate dances in tune with the authentic flavors, while your gaze gets lost in the breathtaking panorama that surrounds you.

Siena , Tuscany

From $ 37.23

Enjoy a wonderful journey into the opera culture of Italy in charming, intimate surroundings, in Siena’s historical centre. Our singers will perform famous pieces from works like La Traviata, La Bohème, Tosca and Madame Butterfly and more for you. Whether you are an Opera lover or simply delight by new experiences, you will be surprised by how many arias will already be familiar. A great opportunity to enjoy a live opera performance in the heart of Italy. Performances start at 9:15 pm Location: Auditorium S.Stefano alla Lizza - Italian Opera in Siena (Piazza la Lizza, 1 - Siena)

Siena , Tuscany

From $ 87.27

Prepare to immerse yourself in a memorable horseback riding experience through the Tuscan countryside, guided by a knowledgeable local equestrian expert. Designed for riders of every skill level, this gentle and scenic tour unfolds at a relaxed pace, giving you time to enjoy sweeping views and hidden landscapes that can only be appreciated on horseback. Expect an unforgettable journey surrounded by Tuscany’s natural beauty one that you’ll remember long after you return home.

Siena , Tuscany

From $ 37.82

Enjoy 1.5 hour wine tasting experience in an elegant medieval Castle in the heart of Montalcino. Together with an expert sommelier, don't miss the chance to discover and taste some of the best Tuscan wines in an exclusive location.

Siena , Tuscany

From $ 87.27

Winery Tour and Wine Tasting in Siena with Afternoon Meal. Immersed in the magical atmosphere of rural Tuscany, just a stone's throw from the old town of medieval Siena, the experience is a journey into the history, culture, tradition, and science that give life to every bottle of our organic wine. During the winery tour we will analyze together the characteristics of the vineyard agro-ecosystem and the techniques used to preserve and regenerate rural resources. In our old wine cellar, we will take you through the fascinating world of winemaking and the secrets behind crafting quality wine. The tour will end in our tasting room, where you will grasp all the organoleptic nuances of our young and vintage wines. Each glass will be paired with the best seasonal Tuscan products, to delight your palate and nourish your soul.

Siena , Tuscany

From $ 87.27

For real wine lovers, This is a wine tasting experience hosted by a Sommelier. This tour offers you an exclusive wine tasting in a Medieval cave dating back to Etruscan period, 600 BC. This place is private and the only one accessible to public. Here you will have one of a kind experience tasting the best wines selection from Sienna's region. Brunello di Montalcino is also in the list of top 100 best wines in the world by the magazine Wine Spectator. Our Licensed Tour Guide will give you an introduction about Sienna history and assist you during the tour giving some tips on where to eat and what do in town during your stay. Please note: This experience being the a private premises is limited to 12 people per day.

Siena , Tuscany

From $ 75.63

Discover the authentic beauty of Tuscany with our tour of vineyards, art and flavors. We start with a walk through the vineyards, immersed in the heart of Chianti, to reach the picturesque church of San Giorgio a Lapi, dating back to 1100. Here you can admire three splendid frescoes by Nasini, a true hidden jewel. After the visit, we will enter our cellars to discover the winemaking and aging process of the wine. And to top it off, a tasting is waiting for you on our panoramic terrace, overlooking the Crete Senesi, accompanied by a lunch with the best typical Tuscan products, all in the shade of an ancient white mulberry tree. Live an unforgettable experience between nature, history and good wine!