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clock-o11 hours (Approx.)
ticket-oMobile ticket
commentOffered in: English and 1 more


Visit San Gimignano, Monteriggioni, and Montalcino on a day trip from Siena, and discover medieval architecture, wine, and stunning views of Tuscany. With ample free time in each of the hill towns, the tour also includes lunch at a Monteriggioni winery plus samples of Chianti and Brunello di Montalcino wine.
  • Day trip to Tuscany’s hill towns from Siena
  • Explore San Gimignano by foot and admire its medieval towers
  • Stop for lunch and Chianti wine at a Monteriggioni winery
  • Travel through the idyllic Val d’Orcia region
  • Sample Brunello di Montalcino wine in Montalcino
Start with a 7:30am or 8:30am hotel pickup, depending on the time of year. As the sights of Siena slip into the distance, you’ll notice the landscape turn into the undulating hills of Tuscany.
Your first stop in the region is the beloved hill town of San Gimignano, a UNESCO World Heritage Site. Enjoy free time here to wander the streets of its historical center, gazing at the medieval architecture, towers, piazzas, and artisan shops. San Gimignano produces the renowned vernaccia wine, and you’ll find plenty of enoteche (wine shops) around the streets.
Next, you’ll head to the historic fortress town of Monteriggioni. The hill town is encircled by intact medieval walls, beautifully preserved from the 12th century. Hear how Dante likened the walls’ towers to the Giants of Inferno in his Divine Comedy as you enter the town, then make your way to a winery for lunch. Savor a light meal of local cheese and salami, paired with Chianti wine.
With your appetite sated, you’ll travel into the Val d’Orcia region of Tuscany where the winemaking village of Montalcino awaits. Taste the esteemed Brunello di Montalcino wine, and learn about the town’s winemaking traditions.
Relax on the journey back to Siena, and finish your day trip with a hotel drop-off.


Viator Traveller's Reviews

12 reviews
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, Aug 2018

First off our guide was amazing, she picked us up from the hotel right on time. She was very knowledgeable and fun. She gave us time to walk around. The wine tasting was fantastic! The wineries were beautiful. It is easy rides everywhere. You get to see a lot. If you like wine, this is a great tour.

, Jun 2018

Transportation was 1,5 hours late and we arrive San Gimignano 2 hours late meaning very little time in San G. I called previous day to the local office and went through that our pick up point Piazza del Mercato Bus stop is easy to come. When we noticed that pick is not going to be on time, I called three times to the local office and they every time promised to call me back and tell the situation. They never called back, which is very unprofessional in this kind of situation. W didn't get any kind of explanation, only sorry and during the trip there was not a single word of guidance. Also because of late arrival to the first wine tasting and lunch, we had to wait in hot sunshine for our turn to get in. This kind of trips are for us once in a lifetime experiences and this we definately remember but not for positive things. We have not received any kind of explanations and/or compensation from the local organizer.

, Apr 2018

Enjoyed the trip through the countryside. Lunch and wine tasting very good. The towns themselves pretty touristy. Could skip the small one in Chianti altogether. Loved the guide.

, Feb 2018

This a Great way to spend the day visiting 2 wineries and visiting beautiful Tuscany towns. Best day trip of our time in Tuscany.

, Nov 2017

We had a fabulous day out with the wonderful Marco as our driver and guide. Our small group comprised five people and although the weather was disastrous heavy rain, thunder and lightning in the morning, Marco gave us options which allowed us to make the most of our day. San Gimignano was brilliant - but we were too early for the Cathedral and the museum. The wine tastings were superb, we had a lot of fun and learned a great deal about Chianti and the history of the area's wine making. Montalcino was also beautiful although most of the shops and cafés were closed due to it being a Sunday. We chose a tour at the end of the season so we were quite prepared for this. We would highly recommend the tour to anyone wanting to get a feel for the real Tuscany!

, Oct 2017

Really enjoyed this tour montes garden was beautiful and we had the perfect amount of time there, the lunch was delicious and in the most beautiful setting Great tour

, Oct 2017

Perfect, relaxed day with generous wine tasting at two wineries.

, Aug 2017

Very good guide. I think one wine tasting visit would have been enough for us. But, having said that still got to see some beautiful Tuscan towns and countryside. We would recommend it.

, Aug 2017

Adel was an interesting tour guide. A sense of humour and a bit of history. Just wright.

, May 2017

This was a really good tour with a good tour group. To have free time in San Gimignano was great and the winery visit, tasting and lunch was superb.
My only suggestion is to skip the Montalcino tasting as the wines were far inferior and detracted from the earlier experience.

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