Top Siena Art & Culture Classes in 2026

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If you've only got limited time in Siena, make sure you maximize your experience of the Tuscan hot spot on a sightseeing tour that includes skip-the-line entry. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo and stroll the streets with your guide, learning about the history of the place and leaving the navigating to someone else. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket.

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Skip the Line: Siena Duomo and City Walking Tour

2 hoursFree Cancellation

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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.

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Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

Price varies by group size

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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.

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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

9 hoursFree Cancellation

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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.

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Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

4 hoursFree Cancellation

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Hidden Castles & Chianti Wine Experience– Small Group

5 hoursFree Cancellation

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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.

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Tuscany Hiking Tour from Siena Including Wine Tasting

4 hoursFree Cancellation

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Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

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San Gimignano, Chianti, and Montalcino Day Trip from Siena

11 hoursFree Cancellation

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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.

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Tuscan Chianti Hills Horseback Riding Tour

1 hour 30 minutesFree Cancellation

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Private Tour: Siena Walking Tour

2 hoursFree Cancellation

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Visit San Gimignano and Volterra the easy way from Siena, on an intimate small-grop tour. Head to the hilltop town of Monteriggioni, then stop for a while in UNESCO World Heritage–listed San Gimignano, with its medieval towers and views over the Tuscan countryside. Drop into an alabaster workshop in Volterra, then indulge in a rustic lunch at a Tuscan farm. Learn about local history and culture along the way.

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Small-Group San Gimignano and Volterra Day Trip from Siena

8 hoursFree Cancellation

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Experience a side of Italy rarely available to visitors when you take a cooking class in the Chianti wine region. During your private session, discover the secrets of Tuscan cuisine, from sauces to tiramisu. After dining on the food you just learned to make, continue on to a vineyard for a complimentary wine tasting and pairing lesson. Round-trip transport from Siena is included for your convenience.

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Private Cooking Class in Chianti from Siena

5 hoursFree Cancellation

Price varies by group size

Must-Dos in Siena

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The magnificent Gothic and Romanesque structure of Siena Cathedral (Duomo).

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Top Siena Art & Culture Classes in 2026

11 results

Must-Dos in Siena

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni

Siena Cathedral (Duomo di Siena)

Piazza del Campo

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni

Siena Cathedral (Duomo di Siena)

Piazza del Campo

Montalcino

Siena Historic Center (Siena Centro Storico)

Mangia Tower (Torre del Mangia)

Monteriggioni