Day trip

From Siena: San Gimignano, Montalcino & Wine Tasting

4.7 / 5

71 reviews

Activity provider: My Tour in Italy

From Siena: San Gimignano, Montalcino & Wine Tasting

Activity provider: My Tour in Italy
Likely to sell out

From US$ 102.61 per person

Likely to sell out

Spend a day in the Tuscan countryside and discover the charms of medieval San Gimignano and Monteriggioni.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Reserve now & pay later
Keep your travel plans flexible—book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures apply. Learn more
Duration 11 hours
Check availability to see starting times.
Live tour guide
English, Italian, Spanish
Pickup included
Your accommodation in Siena.


  • 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.

San Gimignano is also 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.

The tour continues on to Monteriggioni, the ancient crown-shaped fortress that appeared on Italy’s old 100-Lire currency. The 13th-century walls feature 14 towers that Dante likened to the giants in his Inferno.

Afterwards, you’ll stop at a winery for a lunch of salami, cheese, and other local products, accompanied by a tasting of Chianti wines.

Visit 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.

The final stop of the day will be 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)
  • Pick-up service (on request)
  • Travel by air-conditioned minivan (maximum of 8 people)
  • Tips
Not suitable for
  • Wheelchair users
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask

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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.
  • In the absence of the documents required for COVID-19 security measures, it will not be possible to participate in the activity and no refund will be made.
Customer reviews

Overall rating

4.7 /5

based on 71 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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Overall this was a good experience! The tuscany region is incredibly beautiful & having someone drive you to each location in an AC van is hard to beat. The first wine tasting at Poggio ai Laghi was very good and our host was very knowledgeable and entertaining. The final tasting was a bit of a let down as the daughter of the host is usually there to translate in English, so our van driver had to end up translating the whole tasting. The time at the cities was about perfect to walk around and sit & have a coffee. It would have been nice to get a bit more of the history of the area as we approached each new place. We also were never given an outline of the day from the driver, we had to keep asking how long til the next stop and so on. Again overall it was a great experience and we had a blast with our group in the van!

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August 8, 2022

Excursion to do. Too bad we didn't have more time in San Gimignano: in the two hours available my 10-year-old son and I were able to climb the Torre Grossa and visit the Duomo (to do this we had to purchase the cumulative ticket, which included more, but not materially 'it was time ...). We must consider that there are many tourists, so queues and waiting ... we had to give up the world champion ice cream ... In Montalcino there is little to see, if not the magnificent landscape. Our guide / driver Fabio is very generous and nice

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June 25, 2022

We had a wonderful day seeing two gorgeous towns and two delicious winery stops! Our driver, Daniel, was knowledgeable about the landscape, towns, and wines. He even took us to an extra three scenic stops near the towns for photos! The vineyards we stopped at were wonderful small, family-run businesses that showed us how they make their wines, told us about the methods to grow the specific kind of Tuscan wines they produce. We had two delicious meals with several wine samples from each one too! We bought wines from each vineyard and had it shipped home. Be sure to ask for Daniel if you want to get some extra stops to make the trip extra special!

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June 1, 2022

Product ID: 44381