
Small-Group Chianti and San Gimignano Sunset Trip from Siena
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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
4.8/5
Based on 65 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Small-Group Chianti and San Gimignano Sunset Trip from Siena worth booking?
Small-Group Chianti and San Gimignano Sunset Trip from Siena is a 8-hour experience in Siena, Italy, from $190 per person. It scores 78 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.8/5 rating across 65 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 78 / 100
- Rating
- 4.8/5 (65)
- Duration
- 8 hours
- From
- $190 per person
On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine by visiting a local
What you get
- Traditional dinner at farm
- Professional Guide
- Transport by air-conditioned minivan
- Tour of winery with wine tasting
About this experience
On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine by visiting a local producer, touring their cellars and tasting their wines. Then head to the UNESCO World Heritage town of San Gimignano, famous for its medieval towers. Enjoy the main sights and browse the streets and boutique stores just as the day's crowds begin to dwindle. Visit a local farm and enjoy a farm-to-table dinner of its products and wines during sunset, in a stunning location overlooking the San Gimignano towers and the rolling, vine-covered hills.
What's included
Included
- Traditional dinner at farm
- Professional Guide
- Transport by air-conditioned minivan
- Tour of winery with wine tasting
Not included
- Gratuities
- Hotel pickup and drop-off
- Entrance fees to attractions in San Gimignano
What you'll see and do
Basilica Cateriniana Di S. Domenico
Meet your tour guide at 2.30pm in front of the church of San Domenico in Siena and begin the tour with a comfortable drive through the Chianti countryside. Visit a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the wine-making process. Sit down and savor a tasting of Black Rooster Chianti Classico wine.
Pass by without stopping
Cantinetta di Monteriggioni
After visiting a Chianti winery, visit a historic town that was once of fortress, Monteriggioni, to marvel at the medieval towers that are still intact. Monteriggioni is a perfectly preserved medieval town with a complete ring of walls and turrets, once Siena’s main bastion of defense against the armies of Florence. Today it is a quiet hamlet and you can enjoy leisure time exploring the charming streets and stores of local crafts.
30 minutes here
Historic Centre of San Gimignano
In the late afternoon, arrive in San Gimignano as the crowds begin to dwindle and the many streets and squares of this medieval town of towers that flourished thanks to the via Francigena, an important trade route. Enjoy free time to enter its impressive church, the Collegiata di San Gimignano, or to explore the Civic Museum (entrance fees at own expense). Alternatively, shop the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars or discover the town’s many hidden beauties.
60 minutes here
Strada Statale 222 Chiantigiana
After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner accompanied by wine. Enjoy the farm's products and wine over a convivial dinner with the others on tour that you can now call new friends.
120 minutes here · Admission included
Where it starts and ends
Meeting point
Siena
Meet under the large tree next to the red brick church
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Meet under the large tree next to the red brick church
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Wed, Sat
- Group size
- Up to 9 travelers per booking
- Operated by
- Tuscan Escapes by Papilio SRL
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
Photos






Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Wed, Sat
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 23
- Verdict
- Strongly Recommended
Why this scores 78
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Small-Group Chianti and San Gimignano Sunset Trip from Siena: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Small-Group Chianti and San Gimignano Sunset Trip from Siena cost?
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Prices start at $190 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Small-Group Chianti and San Gimignano Sunset Trip from Siena 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 Siena is not rushed.
Is Small-Group Chianti and San Gimignano Sunset Trip from Siena worth it?
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It holds an Outty Ranking of 78 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.8/5 across 65 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule Small-Group Chianti and San Gimignano Sunset Trip from Siena?
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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 Small-Group Chianti and San Gimignano Sunset Trip from Siena 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 Small-Group Chianti and San Gimignano Sunset Trip from Siena?
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Around 23 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 Siena 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 Siena and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does Small-Group Chianti and San Gimignano Sunset Trip from Siena 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 Siena 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 Siena?
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On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Skip the Line: Siena Duomo and City Walking Tour, Siena: A Wine Tour and Tasting Experience. 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 Siena?
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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 Siena?
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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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