
Private Siena & San Gimignano Day from Florence with Chauffeur
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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 Siena & San Gimignano Day from Florence with Chauffeur worth booking?
Private Siena & San Gimignano Day from Florence with Chauffeur is a 8-hour experience in Florence, Italy, from $600 per person. It scores 53 out of 100 on the Outty Ranking, which we label “Worth a Look”, 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
- 53 / 100
- Rating
- 5/5 (5)
- Duration
- 8 hours
- From
- $600 per person
Enjoy a full-day private Siena and San Gimignano experience from Florence, traveling in comfort with your English-speaking driver in a luxury Mercedes-Benz sedan or van. This 8-hour tour leads you through the Tuscan cou
What you get
About this experience
Enjoy a full-day private Siena and San Gimignano experience from Florence, traveling in comfort with your English-speaking driver in a luxury Mercedes-Benz sedan or van. This 8-hour tour leads you through the Tuscan countryside to Siena, a historic medieval city known for its architecture, traditions, and iconic old town. After free time to explore independently, continue to San Gimignano, famous for its medieval towers, charming streets, and panoramic views. Lunch time is scheduled in San Gimignano, with the option to reserve a table at a local restaurant offering traditional Tuscan cuisine and wine. Lunch is not included and is paid directly at the restaurant. Unlike standard group tours, this experience is completely private and fully customizable, with door-to-door service, a relaxed pace, and flexibility throughout the day. Your chauffeur will share local insights and cultural information during transfers. Licensed guides are not included and must be requested in advance.
What's included
Included
- Private English-speaking chauffeur
- Luxury Mercedes-Benz sedan or van
- Pickup and drop-off anywhere in Florence
- Fully customizable itinerary
Not included
- Private licensed tour guides (Available on request)
- Lunch (Available on request)
- Gratuities (Optional)
What you'll see and do
Florence
Pickup directly from your hotel, apartment, or preferred location in Florence. Meet your English-speaking chauffeur, who will be at your disposal for the full 8 hours in a luxury Mercedes-Benz sedan or van. During the drive, your chauffeur will share historical background, cultural insights, and local knowledge about Tuscany and the destinations you’ll visit.
Pass by without stopping
Siena
Arrive in Siena, one of Tuscany’s most atmospheric medieval cities, renowned for its preserved historic center and deep-rooted traditions. Guests will have free time to explore the city independently, soaking in its unique character, narrow streets, and monumental squares at their own pace. Highlights you may see in Siena include: - Piazza del Campo - Siena Cathedral (Duomo di Siena) - Historic Contrade neighborhoods - Medieval streets and viewpoints A private licensed guide can be arranged in advance for a guided walking tour of Siena.
120 minutes here
San Gimignano
After Siena, your chauffeur will drive through the rolling Tuscan countryside to San Gimignano, a UNESCO-listed hill town famous for its skyline of medieval towers. Time is scheduled here for lunch. Optional Lunch Arrangement: Upon request, we can reserve a table at a local restaurant, where guests can enjoy traditional Tuscan cuisine paired with local wine. Lunch is not included and is paid directly at the restaurant.
60 minutes here
San Gimignano
Following lunch, enjoy free time to explore San Gimignano independently. This charming town offers a compact and walkable historic center, perfect for a relaxed visit and scenic views over the countryside. Highlights you may see in San Gimignano include: - Medieval towers (including Torre Grossa) - Piazza della Cisterna - Collegiata di Santa Maria Assunta - Artisan shops and panoramic viewpoints
90 minutes here
Florence
Relax during the scenic drive back to Florence. Drop-off at any location of your choice within the city.
Pass by without stopping
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
- en, it
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Best Rome Driver Private Tours
Know before you go
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Foldable wheelchairs only (Must fit in the vehicle trunk)
- Guests has to be able board the vehicle independently
Photos






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
5 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
1 mentionReviewers describe the commentary as informative rather than scripted.
Organization
1 mentionPickup, timing, and logistics are described as running smoothly.
Food and drink
1 mentionThe tastings and food stops are a highlight for most reviewers.
Good for families
1 mentionReviewers traveling with kids report it landed well with their group.
Traveler reviews
5 verified traveler reviews for Private Siena & San Gimignano Day from Florence with Chauffeur. Ratings and reviews provided by Viator and Tripadvisor.
Best Way To see Siena and San Gimignano
This was one of the best tours! We stayed in Florence for 10 days and explored all of Tuscany. For some days we rented a car. Our last day we booked this tour and it was fabulous. Carlo our driver was polite, extremely knowledgeable and delightful. He made our day trip magical when it could have been miserable had we tried to do this on our own. Our trip was May 15-25. By May 24 the crowds had tripled making many areas feel more like a Disney theme park than peaceful Tuscany. Carlo timed everything perfectly and even brought us to some local restaurants and wineries.
Response from the operator: Dear Jane, Thank you so much for taking the time to leave us such a heartfelt review! We are truly delighted to hear that you had a wonderful experience with us and that our Professional Driver Carlo made your journey so enjoyable. We sincerely hope to have the pleasure of welcoming you back on your next trip to Italy and creating more unforgettable memories together! Saluti from Rome, Best Rome Driver Team
via Viator
Great Driver Ernesto
If I could give six stars, I would — that’s how exceptional Ernesto was as our driver. Over two days, Ernesto was always on time, impeccably dressed, and an absolute pleasure to work with. Having spent my entire career in customer service, I have high standards — and he exceeded every one of them. No matter what we asked, the answer was always “no problem” and “anything you want.” He was easy to communicate with, professional, and his driving was smooth and safe throughout. The vehicle — a beautiful Mercedes-Benz van — was clean and comfortable, making the experience even better for me and my family. Ernesto is a true professional and a tremendous asset. We can’t recommend him highly enough!
Response from the operator: Hello, Thank you so much for taking the time to leave us such a heartfelt review! We are truly delighted to hear that you had a wonderful experience with us and that our Professional Driver Ernesto made your journey so enjoyable. We sincerely hope to have the pleasure of welcoming you back on your next trip to Italy and creating more unforgettable memories together! Saluti from Rome, Best Rome Driver Team
via Tripadvisor
Excellent
Excellent driver very friendly and attentive
Response from the operator: Buongiorno desde Roma! ¡Muchas gracias por su amable apoyo! Esperamos poder mostrarle el resto de Italia en el futuro y tenerlo a bordo con nosotros una vez más. Best Rome Driver Team
via Tripadvisor (translated)
We had an amazing day...
We had an amazing day touring Tuscany and Siena and San Gimignano. Our driver Alessandro was just amazing! He accommodated our every wish and also recommended a wonderful restaurant in San Gimignano named Dulcisinfundo to us. We had a wine tasting there and enjoyed a delicious lunch which highlighted their many specialties. Thank you Alessandro for making our time in Italy so special!
Response from the operator: Dear Cathy, Thank you very very much for your kind support! It's our goal to offer our guests only the best quality services. We are delighted to know that you enjoyed your day tour and that you had great time with your Professional Driver Alessandro! We look forward to showing you the rest of Italy in the future and to having you on board with us once again. Saluti from Rome, Best Rome Driver Team
via Viator
Un hermoso día en la Toscana
Super comfortable and safe car with a wonderful driver and guide, Salvatore, who spoke fluently English and Spanish. He made sure we visited the best places in Siena and San Gimignano. Pasamos un día maravilloso en la Toscana.
Response from the operator: Buongiorno desde Roma! ¡Muchas gracias por su amable apoyo! Esperamos poder mostrarle el resto de Italia en el futuro y tenerlo a bordo con nosotros una vez más. Best Rome Driver Team
via Tripadvisor
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
- 2
- Verdict
- Worth a Look
Why this scores 53
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Siena & San Gimignano Day from Florence with Chauffeur: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Siena & San Gimignano Day from Florence with Chauffeur cost?
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Prices start at $600 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 Siena & San Gimignano Day from Florence with Chauffeur 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 Siena & San Gimignano Day from Florence with Chauffeur worth it?
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It holds an Outty Ranking of 53 out of 100, which we label "Worth a Look". 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 Siena & San Gimignano Day from Florence with Chauffeur?
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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 Siena & San Gimignano Day from Florence with Chauffeur 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 Siena & San Gimignano Day from Florence with Chauffeur?
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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 Siena & San Gimignano Day from Florence with Chauffeur 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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