Private Guided Day Trip 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
5.0/5
Based on 5 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Guided Day Trip Siena, San Gimignano and Chianti worth booking?
Private Guided Day Trip Siena, San Gimignano and Chianti is a 8-hour experience in Florence, Italy, from $153 per person. It scores 63 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 5 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 63 / 100
- Rating
- 5/5 (5)
- Duration
- 8 hours
- From
- $153 per person
• ESPERIENZA PER IL TUO GRUPPO PRIVATO • This GUIDED tour will take you in the morning to visit the city of Siena accompanied by an expert official guide. The afternoon will be dedicated to the discovery of the historica
What you get
About this experience
• ESPERIENZA PER IL TUO GRUPPO PRIVATO • This GUIDED tour will take you in the morning to visit the city of Siena accompanied by an expert official guide. The afternoon will be dedicated to the discovery of the historical wine territory of Chianti. You will have the opportunity to visit some of the most famous vineyards, or small family-owned businesses, see their cellars and taste their excellent food and wines. Lastly, explore the wonderful medieval city of San Gimignano, considered one of the most beautiful historic Italian villages. Add an optional, unforgettable lunch to savor traditional Tuscan wines and specialties in a local organic farm or winery! • 9hr Full-Day private tour of Tuscany from Florence • Licensed TOUR GUIDE in Siena included • Visit the medieval cities of Siena, Monteriggioni, San Gimignano and Fonterutoli • Craft Chianti Classico wine at a local vineyard • Private transportation by Mercedes Minivan air-conditioned
What travelers are saying
Outty’s summary of the themes that recur across 5 traveler reviews. Written by us, not quoted from reviewers.
The guide
4 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
4 mentionsThe tastings and food stops are a highlight for most reviewers.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Value for money
1 mentionTravelers feel they got more than they paid for.
Traveler reviews
5 verified traveler reviews for Private Guided Day Trip Siena, San Gimignano and Chianti. Ratings and reviews provided by Viator and Tripadvisor.
Tuscany tour at its best!
Remarkable Tuscany day trip! Alessandro is an amazing guide. Friendly, knowledgable and an excellent driver. The Tuscan countryside enroute to Siena was stunning. Rolling hills, olive trees and vineyards. Our first stop after leaving Florence was Siena. Siena cathedral is a stunning example of Gothic architecture. Built primarily in the 12th and 13th centuries, the cathedral is laden with black-and-white marble façade. Interior sculptures and paintings are everywhere. After a refreshing affogato, we headed to San Gimignano first stopping for lunch and wine tasting at Tenuta Guardastelle. Nothing short of spectacular and picturesque with amazing wines. Next stop was inside the walls of San Gimignano, a perfect example of a Tuscan medieval city. Lots of shopping for salami's, pecorino, leather and of course gelato. A fantastic tour for sure all thanks to Alessandro. Gratzie!
via Tripadvisor
Superb Tour!
Our family of 6 adults took this day trip/tour with Alessandro in late October 2024. Everything about it was superb! Alex communicated with us after booking and as needed prior to our trip. Door to door service from our hotel, the tour was the right mix of necessary driving with plenty of time in Siena (including a terrific guided walking tour with an excellent local guide from Siena), San Gimignano, and we also chose the optional lunch at the winery which was great. Alex was passionate, knowledgeable and a pleasure to spend time with. He did the little things that made the trip more enjoyable, like letting us know where to get the best views and where to get "the worlds most famous gelato!" As an added bonus, he gave us a great dinner recommendation and contact information that made getting a water taxi in our next stop (Venice) easy! This day was one of the highlights and possibly the most enjoyable day of our two week trip to Italy! Thank you Alessandro!
via Tripadvisor
Alessandro was super...
Alessandro was super helpful and informative. Made sure all our needs were taken care of and was a great guide for the day.
via Viator
Absolutely Amazing! Highly Recommended!
We did a private tour in Tuscany last week with Alessandro which was one of the highlights of our trip to Italy. At around 9:30 am, Alessandro picked us up from our Florence hotel in an air-conditioned Mercedes Benz Minivan. We then then proceeded to visit Siena which is lovely small town in Tuscany, then went on to Chianti on a spectacular drive through the many vineyards and olive farms. Chianti is the main wine region in Tuscany with beautiful landscapes. Alessandro was very knowledgeable about the area and the wine industry. We opted for a lunch at a local farm (and winery) which was truly amazing and highly recommended. We got to sample different types of homemade foods and various local wines. After lunch, we drove through some small and super charming Tuscan villages where we made couple of stops to explore the area. Again, Alessandro was very knowledgeable and went out of his way to give us a lot of valuable and interesting information about the area and these little towns. We then went back to Florence and were dropped back at our hotel. All in all, this is a fantastic trip and great value for your money. Uniquetuscany and Alessandro are your perfect partners for your day trips in Tuscany.
Response from the operator: Hi Zaid! your review is really a pleasure to read, we spent a wonderful day, really a day spent with friends .. Hope to see you both again soon, again a big hug, we will see you soon in Dubai !! Alessandro
via Tripadvisor
Best Florence Private Driver
Out of our 3 weeks in Italy, this day was our favorite! Our driver, Alex, was perfect! He was prompt, had interesting stories and information to share with us, and was a very safe driver. Alex had our entire day planned, which was so appreciated. We started with a visit to Piazza Michelangelo in Florence, and then drove into Tuscany to visit Sienna and San G (I think this is my favorite Italian town!). We visited a private vineyard home and winery, and had a once-in-a-lifetime homemade lunch with wine pairings on their gorgeous property. Alex has the talent to know when to be there with you and talk, and when to let you have your own time and moments. But he always made sure we knew exactly how to reach him, where to meet him, and he guided our excursions perfectly. I hope to visit Florence many more times in my lifetime, and I fully intend to include a tour with Alex each time.
Response from the operator: Thanks so much for the review but above all thanks for the nice words you wrote to me!!!! I still wish you all the best and take care my Friends !! I really hope to see you again soon .. Alex
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Booked in 30 days
- 2
- Verdict
- Solid Choice
Why this scores 63
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Guided Day Trip 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 Day Trip Siena, San Gimignano and Chianti cost?
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Prices start at $153 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 Day Trip Siena, San Gimignano and Chianti 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 Guided Day Trip Siena, San Gimignano and Chianti worth it?
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It holds an Outty Ranking of 63 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 5 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 Day Trip 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 Day Trip Siena, San Gimignano and Chianti 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 Guided Day Trip 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 8-hour experience runs outdoors or after sunset.
Where does Private Guided Day Trip 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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