Tours/San Gimignano/Chianti & Montalcino Wine Tour from San Gimignano
Viator · group up to 30 pax

Chianti & Montalcino Wine Tour from San Gimignano

4.3(6)San Gimignano1 hour
VIATOR3.7(3)TRIPADVISOR5.0(3)

Description

Begin your day by meeting your guide at Porta San Giovanni in San Gimignano. From here, head into the beautiful Tuscan countryside for a wine-tasting experience at a local winery, accompanied by typical regional products and a traditional lunch, offering the perfect introduction to authentic Tuscan flavors. After lunch, continue towards the prestigious wine area of Montalcino, world-famous for Brunello di Montalcino. Here, you will enjoy another wine tasting paired with regional specialties, surrounded by breathtaking vineyard landscapes. Following the tastings, enjoy free time in Montalcino to explore the charming historic center, stroll through its medieval streets, and admire spectacular views over the rolling Tuscan hills. Conclude your tour with a return to San Gimignano, completing a day filled with fine wines, local gastronomy, and the unforgettable beauty of Tuscany.

Tour Options

Chianti & Montalcino Wine Tour

Itinerary

80 min

Break time, Photo stop, Visit, Wine, Lunch, Guided tour, Wine tasting, Shopping, Sightseeing (1.5 hours)

120 min

• Break time, Visit, Wine, Guided tour, Wine tasting, Shopping (30 minutes) • Break time, Photo stop, Visit, Free time, Shopping, Sightseeing, Walk, Self-guided tour (1.5 hours)

Highlights

Air-conditioned minivan or minibus transportation
Lunch
Professional tour leader
2 winery visits
Wine tastings

What's included

Included
Air-conditioned minivan or minibus transportation
Lunch
Professional tour leader
2 winery visits
Wine tastings
Not included
Gratuities

Traveller Ratings

4.3
6 reviews
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Important Information

  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Not recommended for pregnant travelers
  • Suitable for all physical fitness levels
  • Customers must be able to climb and descend stairs.

Reviews(6)

R
Rob_C
June 7, 2026
The places are beautiful....

The places are beautiful. It's hard to go wrong anywhere in this region. The focus seemed to be more on wine education and less on wine tasting. The second place in particular had two tastes that were maybe 1 oz each. That was after driving over an hour to get there. The meeting in the morning was a little difficult as well. When we finally found our guide, we had to walk a quarter mile to the van. At the end, we were dropped off a quarter mile downhill from the meeting point. Everything was fine, but it did seem like a few little tweaks could have made for a much better experience.

C
Christina_F
May 18, 2026
Tasting in Chianti was great, but in Montalcino it was a flop.

Anyone boarding in San Gimignano should know that the tour starts in Siena, so the bus is already half full, and you can only choose from the remaining seats. However, we found it worse/more annoying that the bus after the wine tasting in Montalcino first went to Siena to drop off guests, so we sat on the bus for about 2.5 hours straight. The first wine tasting in the Chianti region was fantastic; although the wines were quite expensive, the entire range was tasted (definitely 7-8 different wines), along with very high-quality vinegars and oils made in-house, and they even refilled our glasses. All participants considered the second wine tasting in Montalcino to be a complete rip-off. You are driven 1.5 hours to Montalcino to taste the famous Brunello di Montalcino, and during the tasting, there were only 3 wines in total, and only one Brunello - and it was the cheapest one. Although the other Brunellos on the wine list were praised, you were not allowed to taste them. Due to this very disappointing second tasting, we found the rather hefty price for the tour overall unjustified. However, our guide Emma and the driver Mohammed were excellent. Emma shared a lot about Tuscany, the individual wine regions, and the production of the wines, and even gave tips for Siena at the end.

J
Jocelyn B
March 31, 2017
My favorite tour this time to Italy...

<p>My favorite tour this time to Italy ! Our first stop we had a sit down wine tasting with Mario @ brunello and it was first class! Then we ate pecorino in pienza and wandered in montepulciano ! Our guide Gabriel was very good ! Great tour</p>

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