
Chianti & Montalcino Wine Tour from San Gimignano
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.3/5
Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Chianti & Montalcino Wine Tour from San Gimignano worth booking?
Chianti & Montalcino Wine Tour from San Gimignano is a 8-hour experience in San Gimignano, Italy, from $166 per person. It scores 61 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.3/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 61 / 100
- Rating
- 4.3/5 (6)
- Duration
- 8 hours
- From
- $166 per person
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
What you get
About this experience
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.
What's included
Included
- Air-conditioned minivan or minibus transportation
- Lunch
- Professional tour leader
- 2 winery visits
- Wine tastings
Not included
- Gratuities
What you'll see and do
Castellina In Chianti
Break time, Photo stop, Visit, Wine, Lunch, Guided tour, Wine tasting, Shopping, Sightseeing (1.5 hours)
80 minutes here
Montalcino
• 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)
120 minutes here
Where it starts and ends
Meeting point
San Gimignano
Meet our guide at: Porta San Giovanni, Via San Giovanni, San Gimignano, Province of Siena, Italy
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Meet our guide at: Porta San Giovanni, Via San Giovanni, San Gimignano, Province of Siena, Italy
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Mon, Thu, Sun
- Group size
- Up to 15 travelers per booking
- Operated by
- myTour in Italy
Know before you go
- 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.
Photos






What travelers are saying
Outty’s summary of the themes that recur across 6 traveler reviews. Written by us, not quoted from reviewers.
The guide
3 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
6 verified traveler reviews for Chianti & Montalcino Wine Tour from San Gimignano. Ratings and reviews provided by Viator and Tripadvisor.
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.
Response from the operator: Dear Customer, Regarding the wine tasting, the experience also focuses on learning about local wines, their traditions, and production, with the tastings varying depending on the winery. As for the pick-up and drop-off, our buses can only stop in designated areas and cannot access smaller or restricted streets, which may require a short walk. Thank you for your understanding. Best regards, My tour in Italy
via Viator
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.
via Viator (translated)
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>
via Viator
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Mon, Thu, Sun
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 2
- Verdict
- Solid Choice
Why this scores 61
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Chianti & Montalcino Wine Tour from San Gimignano: questions travelers ask
Practical detail on this experience, plus the wider planning questions for San Gimignano.
How much does Chianti & Montalcino Wine Tour from San Gimignano cost?
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Prices start at $166 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in San Gimignano usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Chianti & Montalcino Wine Tour from San Gimignano take?
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Plan for about 8 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in San Gimignano is not rushed.
Is Chianti & Montalcino Wine Tour from San Gimignano worth it?
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It holds an Outty Ranking of 61 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.3/5 across 6 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in San Gimignano, and how flexible the cancellation terms are.
Can I cancel or reschedule Chianti & Montalcino Wine Tour from San Gimignano?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Chianti & Montalcino Wine Tour from San Gimignano suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Chianti & Montalcino Wine Tour from San Gimignano?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in San Gimignano can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in San Gimignano and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does Chianti & Montalcino Wine Tour from San Gimignano start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central San Gimignano within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in San Gimignano?
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On Outty we rank every San Gimignano experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Wine and food tasting in an organic family winery, Tuscan Cooking Class, Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit San Gimignano?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in San Gimignano?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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