rovostays·

Cultural & heritage · Siena

Top 10 cultural & heritage things to do in Siena

Heritage walks, museum days, temple complexes, and the kind of guides who explain why a place matters rather than reciting dates. The cultural side of Siena, paced for actual seeing.

  1. Guided Winery Tour and Wine Tasting in Siena, Siena1

    1. Guided Winery Tour and Wine Tasting in Siena

    5.0· 66 reviews· 2.5 hours

    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. Siena Street Food Tour With A Local Guide, Siena2

    2. Siena Street Food Tour With A Local Guide

    5.0· 6 reviews· 3 hours

    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.

  3. Tuscan Vineyard Old Jeep Tour, Wine Tasting & Lunch, Siena3

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

    5.0· 1 reviews· 2 hours

    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.

  1. Siena Underground Wine tasting in a Medieval Cave, Siena4

    4. Siena Underground Wine tasting in a Medieval Cave

    5.0· 56 reviews· 1 hours

    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.

  2. Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better, Siena5

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

    4.9· 219 reviews· 3 hours

    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.

  3. Hot Air Balloon Flight Over Tuscany from Siena, Siena6

    6. Hot Air Balloon Flight Over Tuscany from Siena

    4.8· 138 reviews· 3 hours

    Admire the stunning landscapes of Tuscany from above on an approximately 1-hour hot air balloon flight over the hills of Siena. This is both a peaceful and exciting experience — a gentle journey through the sky, guided safely by our experienced pilots. During the flight, you will reach varying altitudes depending on wind conditions, up to around 3,000 feet, from where you can enjoy unique views of traditional Tuscan villas, historic castles, vineyards, olive groves, and the beautiful rolling countryside around Siena. After landing, to celebrate this unforgettable experience, you will enjoy a toast and a light breakfast with local products and prosecco. Note: flights operate only early in the morning. The exact take-off time varies depending on the season, temperatures, and weather forecast, but it will always be in the early morning hours.

  4. Discover the Medieval Charm of Siena on a Private Walking Tour, Siena7

    7. Discover the Medieval Charm of Siena on a Private Walking Tour

    4.8· 257 reviews

    Decide with your guide if you want to have a 2 or 3 hours tour! Discover the treasures of one of the most beautiful cities in the world through the eyes of a local and immerse yourself in its art, culture and traditions as the horse race the Palio, which takes place twice a year. Stroll in the ancient streets and admire the Basilica of San Domenico, the St. Catherine of Siena Church, Piazza del Campo, Palazzo Pubblico, ancient palaces, the important pilgrims road, the Baptistery and the Cathedral. If you wish, visit also the inside of the Cathedral, where you will admire the artworks of important Italian artists, such as Michelangelo, Donatello and Bernini. If you are more interested in the Palio tradition, we suggest to visit a Contrada Museum. You will find out why this horse race is so important for the Sienese and admire the prizes won over the centuries. Customize your tour with your guide!

  5. Skip the Line: Siena Duomo and City Walking Tour, Siena8

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

    4.8· 745 reviews· 2 hours

    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.

  6. Italian Opera in Siena Experience, Siena9

    9. Italian Opera in Siena Experience

    4.8· 74 reviews· 1.3 hours

    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)

  7. Siena Highlights Private Walking Tour With A Guide (Private Tour), Siena10

    10. Siena Highlights Private Walking Tour With A Guide (Private Tour)

    4.6· 30 reviews· 3 hours

    Commence your journey at the iconic Piazza del Campo, immersing yourself in the vibrant atmosphere of Siena's renowned square. Delve into the city's history at Palazzo Pubblico, an architectural marvel serving as the seat of governance. Meander through historic streets, passing Palazzo Tolomei and Palazzo Salimbeni, both UNESCO-listed treasures. Continue to the Basilica of San Domenico, housing the relics of Saint Catherine, before a visit to the Sanctuary of St. Catherine of Siena. Admire the Baptistery and opt for a guided tour of the awe-inspiring Siena Cathedral, adorned with masterpieces of Italian artistry.

Top places to visit in Siena

See all 20

More in Siena

Other things to do

Cultural & heritage in other destinations

Top cultural & heritage elsewhere

Same category, different cities — hand-picked cultural & heritage experiences across Italy.

See more

Places to see in other destinations

Hand-picked sights, neighbourhoods and landmarks across our destination network.

Visiting Siena?

Stay with Rovostays

Hand-picked, verified serviced apartments — concierge always included.