4.5 star rating: Recommended 28 Reviews

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  • Location: Siena, Italy
  • Duration:  5 hours (approx.)
Spend an afternoon in Tuscany, visiting the small towns of San Gimignano and Castellina in Chianti, on a half-day tour from Siena. Hear the history of the region from an expert guide, and then enjoy some free time to explore the medieval hill town of San Gimignano, discovering sites like Piazza del Duomo and Via Francigena. Then, travel to the heart of the Tuscan hills for a tour of a winery in Castellina in Chianti, where you'll learn about Tuscan wine, and enjoy a wine-tasting session, too!


  • Half-day San Gimignano and Castellina in Chianti tour from Siena
  • Hear tales of San Gimignano’s medieval history from an expert guide
  • Explore the hilltop town at your own pace, seeing sights like Via Francigena and the Collegiata
  • Visit the charming village of Castellina in Chianti and take a tour of a Tuscan winery
  • Learn about wine production in Chianti and discover the difference between Super Tuscan and Gallo Nero wines
  • Sample red and white Tuscan wine during a tasting session, and enjoy a plate of antipasto

Recent Photos of This Tour

What You Can Expect

Chianti Wine Tasting and San Gimignano Day Trip from Siena

Enjoy the views from beautiful San Gimignano!

Meet your guide in central Siena and travel north through the Tuscan countryside by air-conditioned coach. Your destination is San Gimignano, a lovely medieval town complete with old city walls and impressive towers. Perched on a hill overlooking the lush Val d’Elsa valley, the UNESCO-listed town is popular for its views, history and architecture.

Learn all about the town from your guide as you travel, and then enjoy roughly 1.5 hours of free time in San Gimignano to explore at your own pace. Admire the stunning architecture around Piazza della Cisterna and Piazza del Duomo, and have your camera ready for photos by the Collegiata – San Gimignano’s Romanesque cathedral. Perhaps take a stroll along the Via Francigena strip – an ancient pilgrimage road – or visit the shops to browse the locally made handicrafts and beautiful Santa Fina pottery.

Meet your guide at the pre-arranged time and travel deep into the heart of Tuscany, to the famous Chianti region. Gaze out at the emerald green hills, laden with grape vines and olive groves, and stop in the postcard-perfect village of Castellina in Chianti. Visit a renowned winery here for a tour, exploring the cellars, vineyards and bottling rooms of an impressive Tuscan wine estate.

Hear about wine production in the Chianti area – the grapes used, the terrain and the climate – and learn about the different classifications of Tuscan wines, such as Super Tuscans and the prestigious Gallo Nero label. After your tour of the estate, sit down to sample a selection of the best!

Sip on different reds and whites, noting the characteristics that set them apart from other Italian wines. While sampling and discussing the wines, tuck into a selection of typical Tuscan snacks. The dishes vary according to what’s available on the day of your tour, but you can expect delights like garlicky bruschetta, mild cheeses and Tuscan salami or ham; you won’t be disappointed!

After relaxing at the winery, return to your coach for the journey back to Siena. Finish your tour in the early evening back at the start point.

Please note: occasionally this tour may run in reverse order, meaning your visit to Chianti will take place before San Gimignano.

Customer Reviews

5 star rating: Highly Recommended December 2014

Love this tour for the reason which it gives flexibility for your to explore San Gimignano together with a winery visit. As it's a half day tour, it best fits my tight schedule at siena, which let me to do some sightseeing in the morning. Like the winery visit!

5 star rating: Highly Recommended September 2014

This was a great tour and a great way to get into Tuscany without having to drive yourself into the countryside. There were 3 stops on this trip–the small village of Monteriggioni, San Gimigiano, and Tenuta Torciano Winery. Our tour guide was knowledgeable and shared a lot of great info about the two small towns without it being an overkill (or otherwise boring us to death) and gave us time in each town to explore on our own. I loved being free to roam as I pleased and not having to wait for anyone :) We had about 30 minutes in Monteriggioni, just enough time to walk around the village and up on the walls to take photos of picturesque Tuscany! Trust me, you don't need more than 30 minutes, plus there are two other stops on this tour! We had about an hour in San Gimigiano, which again was plenty of time to grab the World's Best Ice Cream and sit and enjoy the view (again a FABULOUS view of the countryside!). Our last stop was at the winery where we had 8 different tastings (5 wines, 3 oils) along with food to accompany it. Our tasting was guided by one of the family members that owns the farm. I learned so much about wine, pairings, and tastings that I will forever remember and apply in real life! Our host was hilarious to top it all off, and that plus the wine meant that everyone was having a ball! I highly recommend this tour if you want to see more of this gorgeous region but don't want to rent a car.

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Tour code: 5919CHIANTISANGIM


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