
Private Excursion to Siena, San Gimignano and Chianti Landscapes
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September 2026
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Who is going?
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 23 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Excursion to Siena, San Gimignano and Chianti Landscapes worth booking?
Private Excursion to Siena, San Gimignano and Chianti Landscapes is a 8-hour experience in Florence, Italy, from $160 per person. It scores 68 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.8/5 rating across 23 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 68 / 100
- Rating
- 4.8/5 (23)
- Duration
- 8 hours
- From
- $160 per person
Embark on an unforgettable private tour starting from your hotel. Visit the historic city of Siena, where you’ll enjoy an exclusive guided tour of its charming medieval center. Wander through the narrow cobblestone stree
What you get
About this experience
Embark on an unforgettable private tour starting from your hotel. Visit the historic city of Siena, where you’ll enjoy an exclusive guided tour of its charming medieval center. Wander through the narrow cobblestone streets, admire its iconic palaces, and visit the famous Piazza del Campo. You'll also get a chance to see the magnificent Palazzo del Comune (exterior) before taking some free time to relax and enjoy lunch (not included). After Siena, your private driver will take you on a scenic drive through the heart of the Chianti region. Delight in panoramic views of the countryside, including a glimpse of the ancient fortified village of Monteriggioni, known for its remarkably preserved 13th-century walls. Your journey continues to San Gimignano, a UNESCO World Heritage site celebrated for its medieval architecture and iconic towers. Here, you’ll have free time to explore this fascinating town at your own pace. The schedule of visits may vary.
What's included
Included
- Pick up and drop off at your Hotel if centrally located in Florence
- Local professional Guide at your side in Siena
- Transport by deluxe air-conditioned vehicle with WIFI on board
- English/Italian speaking driver
Not included
- Gratuities
- Guide Service in San Gimignano
- Entrance fees to the Cathedral in Siena
- Everything not mentioned as Included
What you'll see and do
Piazza del Campo
Meet your private driver at your hotel for a beautiful excursion through the delightful hills of the Chianti countryside,with an ever-changing scenery of vineyards and olive trees. Upon arrival in Siena, your guide will bring you on a private tour of the old city centre: walking along the small medieval streets, admiring the splendid palaces and Piazza del Campo, one of the most beautiful in the world, where you will find the Palazzo del Comune(exterior). Free time for lunch (not included).
240 minutes here · Admission not included
Torre del Mangia
a symbol of Piazza del Campo and one of the highest towers in Italy
Pass by without stopping
Cantinetta di Monteriggioni
From Siena your private driver will bring you through a panoramic road where to admire the vineyards and olive groves in the heart of the Chianti territory. Along the way you could also admire the ancient fortified hamlet of Monteriggioni, a small jewel built during the thirteenth century and embraced by its still intact walls.
Pass by without stopping
Historic Centre of San Gimignano
You reach then SanGimignano, another beautiful town, UNESCO world heritage, where you‘ll be given free time to visit the medieval town planning with the numerous and beautiful towers hence the name "Manhattan of the Middle Ages". Please note that the order of the visits may change
30 minutes here · Admission not included
Piazza Della Cisterna
A stroll in the town center means discovering true jewels of art, among which Piazza della Cisterna, the Dome, Palazzo del Podestà and the Church of Sant'Agostino.
30 minutes here · Admission not included
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.
- Languages
- de, en, it, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- CAF Tour and Travel - Gray Line Florence
Know before you go
- Suitable for all physical fitness levels
Photos






What travelers are saying
Outty’s summary of the themes that recur across 23 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
6 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
5 mentionsThe tastings and food stops are a highlight for most reviewers.
Small groups
3 mentionsThe group size is repeatedly described as intimate rather than packed.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Traveler reviews
23 verified traveler reviews for Private Excursion to Siena, San Gimignano and Chianti Landscapes. Ratings and reviews provided by Viator and Tripadvisor.
Great Excursion
Driver was fun. Good sense of humor; Can't recall his name (he is a Brit who relocated to Italy.) Siena was nice, San Gimignano and Montefrigironi (sp) were terrific. Great trip; great value.
Response from the operator: Dear Michael_H, let us thank you for having joined our of our private tours and having shared your experience with us and our common readers. We are so glad to hear that you have appreciated so much your Private Excursion to Siena, San Gimignano and Chianti Landscapes. See of having been able to let you live exactly the kind of experience that we want all our customers to live, represents the best reward for all the efforts and passion that we daily put in our job. We hope to welcome you soon again in another of our activities. Our Best Regards
via Viator
Siena and San Gimignano Tour Outstanding
Great Driver for the day (Paul) who was super informative and put together a great to a local winery at lunch. Our guide in Siena (Maria) was very well informed and did a great job showing us the city and explaining all of its treasures.
Response from the operator: Dear Passenger28688744083, first of all we want to thank you for having joined one of our Tours! You can't imagine how proud and happy we are reading your review! We started our activity in 1954 and we always do our best to leave a memorable experience in our customers. We thank you so much for sharing your experience with us and hope to meet you again in the future! Our Best Regards
via Viator
Good Side Trip
We were on a Perillo tour highlighting Venice, Florence, and Rome. We spent the better part of a day in Siena and enjoyed the tour very much. The Cathedral was beautiful. The square was a great place to spend the afternoon.
via Tripadvisor
Great excursion
Christian was very informative and cared that we had a great tour. He set up our lunch at a fantastic vineyard as well as a private guide in Siena.
Response from the operator: Dear L2661TBtom, let us thank you for having booked one of our activities and shared your experience with us and our common readers! We are so glad to see that you enjoyed so much your Private Excursion to Siena and San Gimignano from Florence, appreciating the professionalism of the driver Christian, the winery where you had lunch and the private guided tour of Siena! Your review represents the best reward for all the efforts and passion that we daily put in our job, since 1954! We hope to welcome you soon in another of our activities! Our Best Regards
via Tripadvisor
The guide in Siena was great and the...
<p>The guide in Siena was great and the tour was informative. I would plan ahead for a wine tasting, too. We were able to fit one in at the spur of the moment but we ran over time and were charged an additional 70E for the time.</p> <p>The driver was very nice and eager to please but his English wasn't great.</p>
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
- Price range
- $160 to $1127
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 8
- Verdict
- Solid Choice
Why this scores 68
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Excursion to Siena, San Gimignano and Chianti Landscapes: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Excursion to Siena, San Gimignano and Chianti Landscapes cost?
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Prices start at $160 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 Excursion to Siena, San Gimignano and Chianti Landscapes 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 Excursion to Siena, San Gimignano and Chianti Landscapes 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 (4.8/5 across 23 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 Excursion to Siena, San Gimignano and Chianti Landscapes?
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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 Excursion to Siena, San Gimignano and Chianti Landscapes 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 Excursion to Siena, San Gimignano and Chianti Landscapes?
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Around 8 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 Excursion to Siena, San Gimignano and Chianti Landscapes 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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