
Exclusive Siena and San Gimignano Tour & Chianti Wine Experience
Traveler rating
4.6/5
Based on 34 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Exclusive Siena and San Gimignano Tour & Chianti Wine Experience worth booking?
Exclusive Siena and San Gimignano Tour & Chianti Wine Experience is a 10.5-hour experience in Florence, Italy, from $143 per person. It scores 68 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.6/5 rating across 34 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 68 / 100
- Rating
- 4.6/5 (34)
- Duration
- 10.5 hours
- From
- $143 per person
Board a comfortable, fully-equipped GT coach and set off to discover the wonders of Tuscany. The first stop of this small group tour will be the magnificent city of Siena. Here, accompanied by a local guide, you’ll have the opportunity to stroll through the charming streets of the city, admiring the stunning Piazza del Campo and the impressive Siena Cathedral. No trip to Tuscany would be complete without a stop at a Chianti winery. Take a relaxing break during your tour and indulge in a tasting of some of the region's most iconic wines. Alongside the wine, you'll also enjoy a selection of delicious local products, allowing you to savor the authentic flavors of Tuscany. End your journey exploring San Gimignano, known for its 14 medieval towers and breathtaking views of the Tuscan countryside. Wander through its charming streets and piazzas, taking in its well-preserved architecture. A perfect blend of history, beauty, and wine, this tour offers an unforgettable taste of Tuscany!
What you get
About this experience
Board a comfortable, fully-equipped GT coach and set off to discover the wonders of Tuscany. The first stop of this small group tour will be the magnificent city of Siena. Here, accompanied by a local guide, you’ll have the opportunity to stroll through the charming streets of the city, admiring the stunning Piazza del Campo and the impressive Siena Cathedral. No trip to Tuscany would be complete without a stop at a Chianti winery. Take a relaxing break during your tour and indulge in a tasting of some of the region's most iconic wines. Alongside the wine, you'll also enjoy a selection of delicious local products, allowing you to savor the authentic flavors of Tuscany. End your journey exploring San Gimignano, known for its 14 medieval towers and breathtaking views of the Tuscan countryside. Wander through its charming streets and piazzas, taking in its well-preserved architecture. A perfect blend of history, beauty, and wine, this tour offers an unforgettable taste of Tuscany!
What's included
Included
- Expert English Only Tour Leader
- Free time in San Gimignano
- Roundtrip transportation by air-conditioned minibus or minivan with free wi-fi
- 1 Hour English Only Guided tour of Siena with an Expert Local Guide
- Sampling of wines, extra-virgin olive oil and regional products
- Visit of a typical Chianti Winery with wine tasting
- VIP Small Group Tour up to 25 participants
Not included
- Pick up and drop off
- Gratuities
What you'll see and do
Siena
The adventure begins in Siena, a city celebrated for its medieval charm and rich cultural heritage. A local guide will take you through its narrow streets, unveiling centuries of history. Admire the iconic Piazza del Campo, one of Europe’s most renowned squares, famous for hosting the thrilling Palio horse race. Marvel at the stunning Siena Cathedral, a Gothic masterpiece adorned with intricate details, marble floors, and priceless works of art by masters like Michelangelo and Donatello. Experience the lively atmosphere of this historic city, a proud rival of Florence throughout history.
180 minutes here
Piazza Salimbeni
Stroll through Piazza Salimbeni and admire the stunning architecture of the buildings surrounding the square. The iconic Palazzo Salimbeni stands as a symbol of the town’s financial history, offering a glimpse into Siena’s rich past while providing a peaceful and picturesque setting in the heart of the city.
30 minutes here
Duomo di Siena
Follow your guide and admire from the outside the outstanding Duomo di Siena The Duomo di Siena, or Siena Cathedral, is one of the most remarkable examples of Italian Gothic architecture. Dedicated to the Virgin Mary, it was constructed between the 12th and 14th centuries and stands as a symbol of Siena’s rich history and artistic legacy.
30 minutes here · Admission not included
Strada in Chianti
Continue your amazing journew with a visit to a traditional winery in the Chianti region, where you’ll indulge in a guided wine tasting experience. Savor the rich flavors of Chianti Classico and other local varietals, perfectly paired with regional delicacies like pecorino cheese, cured meats, and bruschetta. Learn the secrets of winemaking, from grapevine to glass, and embrace the traditions and passion that define this celebrated wine region.
120 minutes here
San Gimignano
Next, travel through the idyllic Tuscan countryside to reach San Gimignano, a hilltop town often called the "Medieval Manhattan" for its iconic skyline of 14 ancient towers. Explore Piazza della Cisterna and Piazza del Duomo, stroll along charming streets lined with artisan shops, and admire the town’s remarkably preserved medieval architecture. The stunning views of vineyards and olive groves stretching out to the horizon will leave you spellbound, making San Gimignano an unforgettable highlight of your day.
120 minutes here
Piazza Della Cisterna
Make your way to Piazza della Cisterna, the heart of San Gimignano’s historic center, and savor the internationally acclaimed, award-winning gelato from Gelateria Dondoli.
30 minutes here
Collegiata di Santa Maria Assunta - Duomo di San Gimignano
Admire the Duomo of San Gimignano from the outside, with its impressive Romanesque facade and beautiful positioning in the heart of the town, offering a glimpse of its medieval charm and historical significance.
30 minutes here · Admission not included
Rocca of Montestaffoli
Explore the Rocca di Montestaffoli, both from the outside and within, where you can appreciate its imposing structure and wander through its historic interior. From the top, enjoy breathtaking panoramic views of San Gimignano and the surrounding countryside, immersing yourself in the rich medieval heritage of the town.
30 minutes here
Piazza del Campo
Visit one of the most significant squares in the city of Siena and let yourself be captivated by the imposing "Torre del Mangia". Built between 1338 and 1348, it was designed to match the height of the Siena Cathedral's bell tower, symbolizing the harmony between religious and civic authority in the city.
60 minutes here
Where it starts and ends
Meeting point
Florence
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
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
- Thu, Sun
- Group size
- Up to 25 travelers per booking
- Operated by
- Ciao Florence Tours Srl
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- Please inform us of any food intolerance or allergy in advance
- Please note that the given order of the visits may change
Photos






What travelers are saying
Outty’s summary of the themes that recur across 34 traveler reviews. Written by us, not quoted from reviewers.
The guide
7 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
34 verified traveler reviews for Exclusive Siena and San Gimignano Tour & Chianti Wine Experience. Ratings and reviews provided by Viator and Tripadvisor.
Great tour in Tuscany
Diana was great - just the right amount of information, lively, interesting annotates.
via Tripadvisor
Great Tour!
Dianna was a great tour guide! Had a great time and made the tour amazing
via Tripadvisor
San Gimignano/Siena/Winery Tours
We had a full day tour with Christian. We went to San Gimignano and then to a winery. We then went to Siena and then another winery. Christian was very professional, such a pleasure to speak with, and very informative of anything we were curious about. Christian was the best we could have asked for and I am so grateful he gave us a tour. Would recommend him to anyone, anywhere.
via Tripadvisor
Poor value for money
So I booked this tour to take the stress out of driving. I had a man in front of me almost in my lap due to a broken coach seat. We will look at it when we get back to base was not really good enough. As usual, when you go on these trips, there was not enough time spent in any of the areas we visited. We paid 195 Euros to be dragged around on a leash. The guide, although very nice, did just walk on up ahead with her flag, keep up, or get lost, basically. There were elderly people on our trip, and if any of them had fallen or taken ill, she would not have known. The day following this trip, we made our own way to Pisa and Lucca on the train. Much cheaper, I mean 140 Euros cheaper and a much more relaxed day.
via Tripadvisor
Poor value for money
I have mixed feelings. We booked direct through our hotel and it was easy. Location for picking up was straight forward. Once on the coach I had a man almost sitting on my lap the whole journey due to a broken coach seat, there was no option to move as the coach was full. When we stopped, other than Siena we did not get enough time in any of the locations. The time walking to and from meeting points was eating into our short time in each location. The guide, although very pleasant was just walking on ahead with her flag expecting everyone to keep up. We had a few older people on our trip and had they fallen or taken ill she would never have known. She walked to fast and at the back no one could hear her, which left confusion over some of the meeting times. Wine tasting was all about locking you in as their captive audience so they could sell you 60e bottles. Not for me an I won't book another coach tour. We thought we would just try something different this time. Do yourselves a favour hire a car and do the trips as day trips independently. It's cheaper and you can manage your own schedule. I felt like I was just driven to a stop , tipped into a shop or two, left to spend and then be picked up at the end.
via Tripadvisor
Good to know
- Duration
- 10.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Thu, Sun
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 12
- Verdict
- Solid Choice
Who runs this experience
Operated by Ciao Florence Tours Srl, who run 68 experiences we rank across 9 cities, with an average Outty Ranking of 61.8 and 1 in the 90+ Club.
See everything Ciao Florence Tours Srl runsWhy this scores 68
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Exclusive Siena and San Gimignano Tour & Chianti Wine Experience: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Exclusive Siena and San Gimignano Tour & Chianti Wine Experience cost?
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Prices start at $143 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Exclusive Siena and San Gimignano Tour & Chianti Wine Experience take?
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Plan for about 10.5 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 Florence is not rushed.
Is Exclusive Siena and San Gimignano Tour & Chianti Wine Experience worth it?
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It holds an Outty Ranking of 68 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.6/5 across 34 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?
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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 Exclusive Siena and San Gimignano Tour & Chianti Wine Experience suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 10.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?
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Around 12 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 Florence 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 Florence and add a light layer if any part of the 10.5-hour experience runs outdoors or after sunset.
Where does Exclusive Siena and San Gimignano Tour & Chianti Wine Experience 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 Florence 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 Florence?
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On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici -by a storyteller, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner, Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm. 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 Florence?
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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 Florence?
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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.
What is included in Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?
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Included: Expert English Only Tour Leader; Free time in San Gimignano; Roundtrip transportation by air-conditioned minibus or minivan with free wi-fi; 1 Hour English Only Guided tour of Siena with an Expert Local Guide; and Sampling of wines, extra-virgin olive oil and regional products. Not included: Pick up and drop off; and Gratuities. Always check the voucher for the final list before you travel.
Where is the meeting point for Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?
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TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.
What languages is Exclusive Siena and San Gimignano Tour & Chianti Wine Experience offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Exclusive Siena and San Gimignano Tour & Chianti Wine Experience wheelchair or stroller accessible?
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The operator notes: Infants and small children can ride in a pram or stroller; and Infants are required to sit on an adult’s lap. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Exclusive Siena and San Gimignano Tour & Chianti Wine Experience if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Florence. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
What do travelers say about Exclusive Siena and San Gimignano Tour & Chianti Wine Experience?
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Across 34 reviews averaging 4.6 out of 5, recurring themes include the guide, knowledge and storytelling, food and drink. Travelers single out the guide as the reason the experience works.
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