
Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence
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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
4.8/5
Based on 434 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence worth booking?
Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence is a 8-hour experience in Florence, Italy, from $710 per person. It scores 73 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.8/5 rating across 434 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 73 / 100
- Rating
- 4.8/5 (434)
- Duration
- 8 hours
- From
- $710 per person
*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English
What you get
About this experience
*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8 hrs tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni (just if you won't need a stop for lunch) and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * Would you like to have a traditional Italian meal’s experience? We can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lovers.
What's included
Included
- expert english speaking driver
- Bottled water
- Onboard Wi-Fi (on request at reservation)
- In-vehicle air conditioning
- Private luxury car or minivan
- Hotel pickup and drop-off in Florence
Not included
- Full lunch + wine tasting at winery (to be paid on spot) from 50/70 euros per adult
- mance
- Licensed Guide in Siena
What you'll see and do
Siena
Siena is known throughout Italy for the quality of its medieval architecture. Upon arrival, enjoy the best local monuments such as the famous Conch-shaped Piazza del Campo and the outstanding 13th-century Siena Cathedral. Many local shops fill the historic streets of Siena that will allow you to taste or taste local food or buy some gifts!
120 minutes here
San Gimignano
*Option to organize lunch at a Farm/Winery for home made lunch with wine tasting (to be payed on site). We have several options about wineries. (This option will reduce the time in the cities of Siena and/or San Gimignano and exclude Monteriggioni).
120 minutes here
Strada Statale 222 Chiantigiana
We explore the country of Tuscany, we will drive through the chianti hills. Stop for picture!!!!
Pass by without stopping
Historic Centre of San Gimignano
Here we are in the beautiful stronghold of San Gimignano. Freeze at the age 1300dc, San Gimignano a pearl of medieval architecture famous for its houses tower! This is our last spot of the day before returning to Florence
120 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Chianti Drivers private tours
Know before you go
- Specialized infant seats are available
- Infants and small children can ride in a pram or stroller
- Suitable for all physical fitness levels
- A maximum of seven people per booking
Photos






What travelers are saying
Outty’s summary of the themes that recur across 434 traveler reviews. Written by us, not quoted from reviewers.
The guide
9 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
4 mentionsThe views and photo stops come up again and again.
Food and drink
4 mentionsThe tastings and food stops are a highlight for most reviewers.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
434 verified traveler reviews for Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Beautiful Tuscany - Great Tour
Our tour guide Massimo was amazing. he knew all the right places, the right choices. the car was great, and he drove so well. we had a ton of fun.
via Viator
I thought it was pricey...
I thought it was pricey since all we basically had was a driver to the three locations. I was expecting him to be flexible go on country road to take pictures of scenery etc. he did not speak good English even though we request English speaking. The two towns were amazing but an hour at each place is Not enough. The winery was amazing amazing
Response from the operator: Hi Kariann, You booked a Siena San Gimignano tour and not a Chianti tour, that's a whole different story! If you want to see Siena and San Gimignano, there won't be much time for anything else! The drivers all speak proper English, I don't know what you were expecting. Sergio speaks good english and makes that since so many years! He has been at your complete disposal anytime, explaining in Siena and at winery...very strange to hear your words....
via Viator
This was an amazing day...
This was an amazing day trip. Our driver Simone was super friendly and knowledgeable and he was flexible with the itinerary. We got to stop at additional places on the way to the main stops for photos and we even went to a winery we have been keen to visit for ages. Would recommend this for couples or small groups.
Response from the operator: thank you so much Thomas!
via Viator
The Perfect Tuscan Day: Incredible Winery & Guide
Simone picked us up on time. He guided us to our destinations as planned on time. It was hot time of year but he had the car AC cooler than we’ve had the entire trip. It was such a nice break away fro the heat. Some people reviews this was more of a driver than a guide. However, we would have never discovered these places without him. Very knowledgeable, professional and kind! It was expensive for two people and knowing this experience was for up to a group but happy with entire day and was worth it in the end. The winery experience was the best! We paid for light lunch and tasting. It exceeded our expectations, TERRE DI SOVERNAJA in San Gimignano and other fun stops!
Response from the operator: Thanks for your review, we are proud of our drivers and what is said about them. Than you again and see you next time dear!!!
via Tripadvisor
Beautiful scenic day trip to Siena
Our trip to Siena was fabulous and Cosimo made the day extra special. He was super knowledgeable and we enjoyed the special day!
Response from the operator: thank you so much
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
- Every day
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 152
- Verdict
- Strongly Recommended
Why this scores 73
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence cost?
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Prices start at $710 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 Tour in Siena, San Gimignano and Chianti Day Trip from Florence 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 Florence is not rushed.
Is Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence 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 (4.8/5 across 434 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 Tour in Siena, San Gimignano and Chianti Day Trip from Florence?
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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 Tour in Siena, San Gimignano and Chianti Day Trip from Florence 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 Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence?
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Around 152 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 8-hour experience runs outdoors or after sunset.
Where does Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence 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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