Private guided tour: Siena San Gimignano and Chianti
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September 2026
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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
3.5/5
Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private guided tour: Siena San Gimignano and Chianti worth booking?
Private guided tour: Siena San Gimignano and Chianti is a 10-hour experience in Florence, Italy, from $150 per person. It scores 54 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 3.5/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 54 / 100
- Rating
- 3.5/5 (6)
- Duration
- 10 hours
- From
- $150 per person
Get a tour of San Gimignano, Siena and the Chianti region during this 10-hour p excursion from Florence. Travel comfortably with a minivan or a car, with much less walking than on a bus. With a dedicated driver/guide,
What you get
About this experience
Get a tour of San Gimignano, Siena and the Chianti region during this 10-hour p excursion from Florence. Travel comfortably with a minivan or a car, with much less walking than on a bus. With a dedicated driver/guide, explore the middle age stronghold of Castellina in Chianti, deep in the Chianti Classico wine area and the square of Siena and San Gimignano, then pop into a local winery to learn about the local sangiovese grapes and sip some Chianti. Wine tasting and round-trip private transportation from a meeting point near the Florence train station included. Highlights 11-hour tour of the Tuscan San Gimignano, Siena and Chianti region from Florence Round-trip transportation from the Florence train station Visit San Gimignano, Siena and Greve Taste Chianti and learn about the cultivation of sangiovese.
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
5 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
4 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Pace and timing
2 mentionsSeveral reviewers found the schedule tight or the day long.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
6 verified traveler reviews for Private guided tour: Siena San Gimignano and Chianti. Ratings and reviews provided by Viator and Tripadvisor.
Excellent guide and unique experience with Matthew in Tuscany
Excellent guide and unique experience with Matthew in Tuscany We had the pleasure of having Matthew as our guide on a private tour of Tuscany, including Siena and San Gimignano, and it was an exceptional experience. From the beginning, Matthew showed a deep knowledge and passion for the history, culture and secrets of the region. It took us to stunning places, giving us fascinating details about each site, which we would otherwise have missed had we travelled on our own. He not only gave us historical information, but also shared local recommendations on food, wine and traditions that made our trip even more special. In addition, his friendly, patient and always willing to answer our questions made the tour even more enjoyable. If you are looking for an authentic and enriching experience in Tuscany, I definitely recommend Matthew as your guide. It was an unforgettable day!
via Tripadvisor (translated)
Fabulous tour through Tuscany
The tour was great! We visited 3 amazing cities with a driver and guide. They were flexible with time and let us tweak and spend the time in the cities as we wished. Wonderful country and unbelievable views! The winery in Chianti was fabulous and a quiet refuge for us after busy days in Florence and Rome! Accents a wee bit hard to follow at times but they were good and kind. We loved this day with our family!
via Viator
DISAPPOINTING
My friend and I booked this small group tour as it was our first time in the Siena/Chianti/San Gimignano area. We expected a guided tour of the town's history and culture but instead were left to walk around on our own for the most part. The reservation stated we would all be meeting at a designated spot in Florence, however, on the day of the tour we showed up only to be left waiting approximately 15 minutes until we contacted the tour guide directly and he told us he was at our hotel; something we did not discuss (would have been very convenient had we known). Upon his arrival, our tour guide appeared annoyed and had no type of identification that would confirm he was the person we were expecting. He was disorganized and unprofessional. After realizing it would be just us on the tour, we asked his name and went on our way. Simon (our tour guide) drove us up to the mountains without giving any sort of plan or itinerary. We followed him around and asked him questions, but he did not demonstrate initiative in actually leading the tour. One part of the visit to Chianti included a private wine tasting, where he proceeded to awkwardly sit with us the entire time. We felt very uncomfortable with him there, and to be quite honest, the whole experience was unsettling. Other than how he led the tour (or didn't), his worst feature was the fact that he kept asking us very personal questions regarding politics and personal finances. Overall, the description of the package was unclear, and the experience itself did not measure up.
Response from the operator: What sad people. You are critizazing somebody that went to pick you up to your hotel. You had a private tour that we should have canceled but tried to give you it even if we lost money. Driver guide is somebody that drives and gives information on the way. If you want a guide has well this is minimum 50 euros extra an hour.
via Viator
Forced March and Bus Ride with Lunch
If you want to walk six miles at a brisk pace, ride 8 hours on a bus, get a 1 hour guided tour in Sienna and have to search for bathrooms on your own this is for you.
Response from the operator: The client has reviewed unfortunately for us a different tour. We only have minivan or sedan tours, with next to zero walking and personable. I wish people would be more considerate when writing, you have real business with families.
via Tripadvisor
Wow, ended up being only the 3 of us...
<p>Wow, ended up being only the 3 of us plus our guide. What a great way to learn about the country and cities. Awesome.</p>
via Viator
Good to know
- Duration
- 10 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Booked in 30 days
- 2
- Verdict
- Worth a Look
Why this scores 54
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private guided tour: Siena San Gimignano and Chianti: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private guided tour: Siena San Gimignano and Chianti cost?
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Prices start at $150 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 Private guided tour: Siena San Gimignano and Chianti take?
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Plan for about 10 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 Private guided tour: Siena San Gimignano and Chianti worth it?
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It holds an Outty Ranking of 54 out of 100, which we label "Worth a Look". That score blends traveler sentiment (3.5/5 across 6 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 Private guided tour: Siena San Gimignano and Chianti?
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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 Private guided tour: Siena San Gimignano and Chianti suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 10-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private guided tour: Siena San Gimignano and Chianti?
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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 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-hour experience runs outdoors or after sunset.
Where does Private guided tour: Siena San Gimignano and Chianti 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 Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. 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.
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