5 of the Best Siena Wine Tastings & Tours

by Paul Joseph  |  Published June 5, 2024

Surrounded by hills covered with olive groves and vineyards, the city of Siena in central Italy’s Tuscany region is the perfect base for embarking on a wine tour.

(Photo: Mi diverto / Courtesy GetYourGuide)

With its UNESCO-listed historic centre, the medieval city draws huge numbers of visitors every year. And for those with an interest in wine, Siena offers double dividends, with the surrounding countryside laying claim to producing some of Italy’s most prestigious appellations. While sampling some of the local tipple outside a pretty enoteca certainly has its appeal, you can’t beat a guided tour for really immersing yourself in the area’s wine scene. With all the intricacy and care of a grape-picker, we’ve selected 5 of the best Siena wine-tasting and tour experiences below.

Great wine tasting in Etruscan crypt

Sample some of the best Tuscan wines in the atmospheric environs of an Etruscan crypt during this 1-hour small-group tour. After meeting on a designated street in central Siena, you and your group will be guided down into a secret underground location, only discovered during renovation work by the owner of a wine store situated above ground. During the subterranean experience, you’ll get to taste a selection of wines from more than a thousand different labels, all accompanied by pecorino cheese served with breadsticks. After returning to level ground, you’ll have a chance to look around the wine store and perhaps pick up a bottle or two to enjoy over dinner or take home with you as a memento of gift. From €115 per person.

Book at GetYourGuide

Tuk Tuk Tour with Wine Tasting

(Photo: Pedaliamo Cycling Tours / Courtesy GetYourGuide)

This 3-hour tour invites visitors to explore the wine region around Siena with the wind in your hair aboard a fun-filled – and environmentally friendly – tuk-tuk. During the panoramic tour, you and your group of up to four guests will traverse the scenic countryside close to the city aboard your quirky electric transportation as you make your way to a local winery, where you’ll get to taste local wine and learn about the intricacies of the wine-making production process, as well as the history of the region. The tour price includes pick-up and drop-off in Siena. From €130 per person.

Book at GetYourGuide

Educational visit with tasting and light lunch

Just two kilometres from central Siena sits Azienda Agricola La Lastra, an organic, family-run farm that hosts daily educational visits complete with wine tastings and a delicious light lunch. During the fully guided 3-hour experience, you’ll discover how organic wine is made, from the winter pruning of the vines, to the agronomic, phenological and biological cycle, all the way through to the final product. You’ll also get to explore the farm’s historic cellar where you’ll receive more fascinating insights into the processes necessary for quality wine production. Included in the tour price are 5 wine tastings, lunch and a bottle of water From €85 per person.

Book at Winealist

Exclusive Winery Tour and Wine Tasting 

(Photo: Azienda Agricola La Lastra / Courtesy GetYourGuide)

Combine an exclusive tour of one of Tuscany’s most acclaimed organic wineries with a full sit-down lunch comprising local delicacies and dishes during this immersive and mouth-watering small-group tour. Over the course of 3.5 hours, you’ll visit a renowned organic winery where you’ll visit the lush vineyards, learn about sustainable viticulture and enjoy a guided sensory wine tasting session of vintage and private reserve organic wines. To conclude the tour in delectable style, you’ll tuck into a gourmet lunch, complete with food expertly paired with your wines. From €150 per person.

Book at GetYourGuide

Food and Wine Walking Tour

There’s no better way of getting to know a place than by walking its streets, taking in the sights, sounds and aromas as you go. This 2-hour excursion combines a guided walking tour of Siena with the chance to savour regional wines and food. As you and your group navigate the city in the company of an expert guide, you’ll stop at various foodie hotspots to sample the local fare. There’ll be cheeses, cured cuts, truffles and olive oil, all paired with an enticing mix of Tuscan white and red wines. There’ll also be a chance to meet and engage with food and wine purveyors, who will be ready to share their knowledge on how the region’s produce is connected to its history and traditions. From €59 per person.

Book at GetYourGuide