The 15 best things to do in Siena (2026)

The ranked list

1. 

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

   Outty Ranking91

   Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover the cellars where these incredible wines age, meet the. 90+ Club at 91/100, 4.9/5 from 1,026 traveler reviews, 9h from $220, free cancellation, an Outty 90+ Club member.

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2. 

   2. Siena: A Wine Tour and Tasting Experience

   Outty Ranking91

   In the hills of the gorgeous Tuscan countryside, just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine and Life' is a 3-hour tour held in an organic winery. Learn about the. 90+ Club at 91/100, 5.0/5 from 399 traveler reviews, 3h from $98, free cancellation, an Outty 90+ Club member.

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3. 

   3. Small-Group Montepulciano and Pienza Day Trip from Siena

   Outty Ranking89

   Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected. Exceptional at 89/100, 4.9/5 from 332 traveler reviews, 8h from $220, free cancellation.

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4. 

   4. Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better

   Outty Ranking88

   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 fam. Exceptional at 88/100, 4.9/5 from 244 traveler reviews, 3h from $85, free cancellation.

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5. 

   5. Wine Class - Tuscan Classics

   Outty Ranking88

   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 a. Exceptional at 88/100, 4.9/5 from 266 traveler reviews, 2h from $70, free cancellation.

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6. 

   6. Skip the Line: Siena Duomo and City Walking Tour

   Outty Ranking87

   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 Cat. Exceptional at 87/100, 4.8/5 from 800 traveler reviews, 2h from $46, free cancellation.

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7. 

   7. Small-Group San Gimignano and Volterra Day Trip from Siena

   Outty Ranking87

   Embrace the medieval charms of Tuscany's towns on a full-day trip to San Gimignano and Volterra from Siena. With an attentive local guide, walk round the Fortress of Monteriggioni, explore the UNESCO World Heritage-liste. Exceptional at 87/100, 4.9/5 from 201 traveler reviews, 8h from $220, free cancellation.

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8. 

   8. A Brunello Cooking Class with Vineyards View Winery

   Outty Ranking86

   Brunello Cooking Class with Chef Alexandra - Cooking class with a view in the morning, followed by Lunch pairing with Brunello wines! With the guidance of our chef Alexandra, you will learn to make classic Tuscan dishes. Exceptional at 86/100, 5.0/5 from 324 traveler reviews, 4h from $300, free cancellation.

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9. 

   9. Tuscany Hiking Tour from Siena Including Wine Tasting

   Outty Ranking86

   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 he. Exceptional at 86/100, 4.9/5 from 122 traveler reviews, 4h from $70, free cancellation.

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10. 

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

    Outty Ranking85

    Tuscan Cooking Class. Cooking Class of a traditional Tuscan meal from starter to dessert including a fresh local handmade pasta. At the end of the lesson dinner is served with what we have prepared during the class, acco. Exceptional at 85/100, 4.8/5 from 357 traveler reviews, 4h from $151, free cancellation.

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11. 

    11. Small-Group Chianti Trip with Wine Tasting from Siena

    Outty Ranking84

    Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian castles are a must-see for any visitor to the regio. Exceptional at 84/100, 5.0/5 from 82 traveler reviews, 8h from $220, free cancellation.

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12. 

    12. Classic Wine Tasting with Traditional Tuscan Products

    Outty Ranking83

    There are places you visit and others you live. A few minutes from Siena, between the Chianti hills and the Crete Senesi, the experience slowly takes shape on our panoramic terrace, in the shade of an ancient white mulbe. Exceptional at 83/100, 4.9/5 from 80 traveler reviews, 1.5h from $32, free cancellation.

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13. 

    13. Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

    Outty Ranking82

    Our driver guide will collect you at the designated meeting point, setting off toward Montalcino. Start this full-day tour with a lesser-known boutique vineyard with high-quality wines. You will taste all their full-bo. Exceptional at 82/100, 4.9/5 from 110 traveler reviews, 8h from $265, free cancellation.

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14. 

    14. Guided Winery Tour and Wine Tasting in Siena

    Outty Ranking82

    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, cul. Exceptional at 82/100, 5.0/5 from 77 traveler reviews, 2.5h from $87, free cancellation.

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15. 

    15. Small-Group Tuscan Cooking Class with Wine & Lunch from Siena

    Outty Ranking82

    Join in a captivating 4-hour small group cooking class, led by a talented multi-lingual chef. Uncover the secrets behind beloved Tuscan dishes in a professional kitchen setting. Learn Tuscan cooking techniques, ingredien. Exceptional at 82/100, 4.8/5 from 178 traveler reviews, 4h from $133, free cancellation.

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