
San Gimignano, Chianti, and Montalcino Day Trip from Siena
Traveler rating
4.3/5
Based on 152 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is San Gimignano, Chianti, and Montalcino Day Trip from Siena worth booking?
San Gimignano, Chianti, and Montalcino Day Trip from Siena is a 11-hour experience in Siena, Italy, from $85 per person. It scores 73 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.3/5 rating across 152 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 73 / 100
- Rating
- 4.3/5 (152)
- Duration
- 11 hours
- From
- $85 per person
Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards of Chianti, taste the famed Brunello di Mo
What you get
- Expert multilingual escorts
- Lunch
- Olive oil and balsamic vinegar sampling
- Alcoholic beverages
- Meals
- Tour of 2 wine estates, one of which is exclusive + 2 wine tastings
About this experience
Spend an unforgettable day exploring Italy’s iconic hill-towns and world-class wineries. Starting from Siena, wander the medieval streets of San Gimignano, soak in the vineyards of Chianti, taste the famed Brunello di Montalcino, and savour local snacks, olive oil and balsamic vinegar – all in a comfortable small-group vehicle.Travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people. Note:Wine tastings take place in English, with your tour leader providing translation support when needed. A moderate amount of stairs and walking is involved During special events, opening times can change The tour itinerary may change, but all tour stops will be visited
What's included
Included
- Expert multilingual escorts
- Lunch
- Olive oil and balsamic vinegar sampling
- Alcoholic beverages
- Meals
- Tour of 2 wine estates, one of which is exclusive + 2 wine tastings
Not included
- Gratuities
What you'll see and do
San Gimignano 1300
Free time in San Gimignano
60 minutes here
Collegiata di Santa Maria Assunta - Duomo di San Gimignano
During your free time opt to visit the Cathedral of San Gimignano
15 minutes here · Admission not included
Piazza Della Cisterna
Free time in San Gimignano
15 minutes here
Palazzo Pubblico e Torre Grossa
Free time in San Gimignano
15 minutes here · Admission not included
Strada Statale 222 Chiantigiana
Lunch and wine tasting in a local winery in Montalcino
60 minutes here · Admission included
Fortezza di Montalcino
Free time in Montalcino
60 minutes here
San Filippo Montalcino
Free time in Montalcino
Pass by without stopping
Val D'Orcia
Spend some time in the stunning Orcia Valley
60 minutes here
Siena
Start your trip at Siena Station Ferrovia, where you will meet the staff. You will recognize them by their green shirt. You will travel by minivan.
40 minutes here
Where it starts and ends
Meeting point
Siena
Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance.
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 8 travelers per booking
- Operated by
- myTour in Italy
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
- Suitable for all physical fitness levels
- Customers must be able to climb and descend stairs.
- Vegetarian option is available for the optional lunch, please advise any specific dietary requirements at time of booking
- Travel in air-conditioned minivan for up to 8 people or minibus for up to 30 people
- Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance.
Photos






Good to know
- Duration
- 11 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Mon, Thu, Sun
- Price range
- $85 to $140
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 53
- Verdict
- Strongly Recommended
Who runs this experience
Operated by myTour in Italy, who run 51 experiences we rank across 5 cities, with an average Outty Ranking of 57.8.
See everything myTour in Italy runsWhy this scores 73
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
San Gimignano, Chianti, and Montalcino Day Trip from Siena: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does San Gimignano, Chianti, and Montalcino Day Trip from Siena cost?
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Prices start at $85 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 San Gimignano, Chianti, and Montalcino Day Trip from Siena take?
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Plan for about 11 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 San Gimignano, Chianti, and Montalcino Day Trip from Siena worth it?
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It holds an Outty Ranking of 73 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.3/5 across 152 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule San Gimignano, Chianti, and Montalcino Day 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 San Gimignano, Chianti, and Montalcino Day Trip from Siena suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 11-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book San Gimignano, Chianti, and Montalcino Day Trip from Siena?
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Around 53 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 11-hour experience runs outdoors or after sunset.
Where does San Gimignano, Chianti, and Montalcino Day 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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