Day trip

From Siena: San Gimignano, Montalcino & Wine Tasting

4.7 / 5

93 reviews

Activity provider: My Tour in Italy
Day trip

From Siena: San Gimignano, Montalcino & Wine Tasting

Activity provider: My Tour in Italy

From US$ 118.36 per person

Spend a day in the Tuscan countryside and discover the charms of medieval San Gimignano, Chianti, and Montalcino. Enjoy a wine tasting and a light lunch at a Chianti winery.

About this activity

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Duration 11 hours
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Live tour guide
English, Spanish, Italian


  • Taste the delicious flavors of local salami, cheese, and more
  • Marvel at the walled medieval town of San Gimignano
  • Explore the Chianti region; enjoy a wine tasting and light lunch
  • Taste world-renowned Brunello of Montalcino at a wine cellar
  • Visit the UNESCO World Heritage Site of Val d'Orcia
Full description

The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops.

Visit San Gimignano, the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. Afterwards, stop at a winery for a lunch of salami, cheese, and other local products, accompanied by Chianti tasting. 

Discover Val d’Orcia, another Tuscan jewel and a UNESCO World Heritage Site. Continue on to Montalcino, perched on a hill overlooking 1,500 hectares of Brunello vineyards that have contributed to the area’s international reputation.

Finally, enter a local wine cellar, where you’ll have a chance to taste the renowned Brunello of Montalcino, rated among the finest Italian DOCG wines. Sample other typical local products as well.

  • Expert bilingual (English/Italian) tour escort
  • Visit to San Gimignano (with free time)
  • Lunch and wine tasting at a farm in the Chianti region
  • Visit to Montalcino and its fortress (with a brief shopping stop)
  • Wine tasting at a renowned winery in Montalcino
  • Samples of typical Tuscan food
  • Opportunity to purchase wine from the winery at special prices (shipping available to most countries)
  • Pickup service within a 6 mile (10 km) radius of Siena
  • Travel by air-conditioned minivan (maximum of 8 people)
  • Tips
Not suitable for
  • Wheelchair users

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Important information

Know before you go

  • For light lunch a vegetarian menu is available upon request
  • Customers must be able to climb and descend stairs
  • The pickup and drop-off service is available and included within a 10 kilometer radius from the center of Siena
  • This tour requires a minimum of 2 participants
Customer reviews

Overall rating

4.7 /5

based on 93 reviews

Review summary

  • Guide
  • Transportation
  • Service
  • Organization

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Had a wonderful time in beautiful San Gimignano, and the wineries. Montalcino, though beautiful, everything was closed so we really only saw the fort. Our driver, Vincenzo, was super sweet and knowledgeable and took us to some great panoramic views to take pictures.. Like other reviews, the trip did last about 9 hrs, which is more than enough time.

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March 25, 2023

Fabulous driver/guide who could speak multiple languages really well and had deep local knowledge (including winemaking processes), lovely comfortable vehicle to travel in, stunning scenery, the right amount of time in each town and wine tasting with genuine local authentic quality wine makers (plus lovely food). We highly recommend this trip!

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March 25, 2023

The small group was perfect for us, and our guide & driver was knowledgeable & friendly - we love San Gimignano but wished we could have had a bit longer to wander the streets & shop. Maybe even a shorter time at Montolcino, the view from the top of the castle is worth it but 20 minutes is all one needs. We enjoyed the wine tastings but found the 2nd stop at the “black tower” more interesting & professional - it was a great day and definitely a highlight of our travels Grazie

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March 25, 2023

Product ID: 44381