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Things to do in Siena

30 experiences — hand-picked & rephrased

Top 25 things to do in Siena

  1. Guided Winery Tour and Wine Tasting in Siena, Siena01

    1. Guided Winery Tour and Wine Tasting in Siena

    5.0· 66 reviews2.5 hoursFrom₹8,521/ person
    Free cancellationInstant confirmation

    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.

  2. Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour, Siena02

    2. Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

    5.0· 34 reviews8 hoursFrom₹79,533/ person
    Free cancellation

    Taste Tuscany's delicious cheeses and the great Brunello di Montalcino red wines on a full-day private guided tour. See the beautiful Val d'Orcia and receive a tour of an organic dairy farm followed by a cheese tasting. Visit the beautiful Renaissance gem that is the hilltown of Pienza and enjoy lunch at your own leisure. Explore the hill town of Montalcino, and taste the rich flavours of the famous Brunello wine directly from a producer. Visit the farm, tour the cellars and learn more about this memorable nectar.

  3. Siena Street Food Tour With A Local Guide, Siena03

    3. Siena Street Food Tour With A Local Guide

    5.0· 6 reviews3 hoursFrom₹9,658/ person
    Free cancellationInstant confirmation

    Indulge in Siena's culinary treasures on a private tour designed to delight your palate, led by an expert local guide. Stroll through charming cobblestone streets, where the enticing aromas from bustling food stalls beckon. Begin your epicurean journey with the crispy perfection of coccoli, drizzled with aromatic olive oil, and savor the multi-layered flavors of savory panini, each bite a testament to Siena's rich gastronomic heritage. As you meander through the city, your guide will share enthralling tales of Siena's history, blending tradition with modern culinary innovations. Discover how the city's vibrant food scene reflects its cultural tapestry, making this tour an ideal exploration for devoted foodies and curious travelers alike. Each stop unveils a new chapter in Siena's epicurean story, promising a memorable adventure that intertwines taste and tradition in the heart of this historic city.

  4. Siena Small group Cooking Class in a Chianti Farm, Siena04

    4. Siena Small group Cooking Class in a Chianti Farm

    5.0· 5 reviews3.5 hoursFrom₹11,362/ person
    Free cancellationInstant confirmation

    Your cooking class is based on a traditional Tuscan Chianti Farmhouse with an expert Italian chef which has ma y years of experience. It is a fun experience which will let you feel the emotions of the Tuscany region and an unique experience with a wonderful view of the Chianti hills. It is a full immersion on the roots of uscany so you can understand better the process of making homemade pasta and typical desserts.

  5. Siena Private Highlights and Hidden Gems Walking Tour, Siena05

    5. Siena Private Highlights and Hidden Gems Walking Tour

    5.0· 5 reviewsFrom₹8,652/ person
    Free cancellationInstant confirmation

    This walking tour offers a truly local take on Siena, far beyond the postcard views. With your host, you’ll explore hidden chapels, medieval backstreets, peaceful gardens, and the living traditions of the Palio and contrade. Whether you're tracing the path of a district rivalry, admiring Gothic architecture, or sipping wine in a tucked-away enoteca, this is your chance to explore like a local, not a tourist. After booking, you’ll receive a short questionnaire to share your interests and travel style. Based on your responses, you’ll be matched with a like-minded host who will contact you directly to suggest a personalized itinerary. You’ll agree on a meeting point and time, and your route can adapt throughout the day based on what captures your interest.

  6. Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch, Siena06

    6. Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch

    5.0· 1 reviews2 hoursFrom₹10,226/ person
    Free cancellationInstant confirmation

    Off-road mini tour in a vintage Jeep through the landscapes of the vineyards. Taste Poggio ai Laghi premium wines, oils & vinegars. Enjoy the Tuscan Appetizers that enhance the flavors of each wine. Our wine expert will enhance this experience with Art & History.

  7. A Brunello Cooking Class with Vineyards View Winery, Siena07

    7. A Brunello Cooking Class with Vineyards View Winery

    5.0· 237 reviews4 hoursFrom₹29,427/ person
    Free cancellationInstant confirmationLikely to sell out

    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 using the finest local delicacies, after which you will enjoy a private tour of the vineyards and the XV century castle that’s been in the family for 17 generations. Enjoy the lunch you prepared yourself on our panoramic terrace overlooking the rolling hills of Montalcino wine country. Each dish will be expertly paired with our own wine production. Tour Length: 4 hours ( Class + Lunch ) - Every day Departure Point:  Possible add-on we can organize for you PICK-UP DROP OFF IN THE PROVINCE OF SIENA Meeting time: 10.00 am Popularity: *****  (best seller wine and food tour in Tuscany) INCLUDED:  All Included  ( Cooking lesson, Tours, Tasting Lunch, Extra optional Transportation from and to the cooking venue )

  8. Siena Underground Wine tasting in a Medieval Cave, Siena08

    8. Siena Underground Wine tasting in a Medieval Cave

    5.0· 56 reviews1 hoursFrom₹8,521/ person
    Free cancellationInstant confirmation

    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.

  9. Siena: A Wine Tour and Tasting Experience, Siena09

    9. Siena: A Wine Tour and Tasting Experience

    5.0· 378 reviews3 hoursFrom₹9,658/ person
    Free cancellationInstant confirmation

    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 different stages of wine making through the seasons and enjoy tastings and a light lunch.

  10. Private Tour: Secret Siena Walking Tour, Siena10

    10. Private Tour: Secret Siena Walking Tour

    5.0· 112 reviews3 hoursFrom₹31,813/ person
    Free cancellation

    Discover the older parts of Siena’s medieval centre and see hidden corners away from the crowded tourist areas, an exceptional itinerary to discover the quieter side of Siena.

  11. Small-Group San Gimignano and Volterra Day Trip from Siena, Siena11

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

    4.9· 193 reviews8 hoursFrom₹21,588/ person
    Free cancellation

    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-listed town of San Gimignano, and visit an alabaster workshop in Volterra. Enjoy a delicious lunch on a small Tuscan farm and spend time at your leisure exploring these rustic hill towns that are steeped in rich Italian history. Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.

  12. Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better, Siena12

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

    4.9· 219 reviews3 hoursFrom₹8,294/ person
    Free cancellationInstant confirmation

    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.

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The activities ranked above are sorted by traveller rating and review count — start with the top 3 if you're short on time. Siena is strongest on heritage walks, food tours and outdoor day trips; the listicle covers all three categories. Most experiences are 3–6 hours and can be combined with a morning visit to a landmark.

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