
Private Day Trip Siena, San Gimignano and Chianti from Florence
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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
5.0/5
Based on 264 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Day Trip Siena, San Gimignano and Chianti from Florence worth booking?
Private Day Trip Siena, San Gimignano and Chianti from Florence is a 8-hour experience in Florence, Italy, from $125 per person. It scores 88 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 5/5 rating across 264 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 88 / 100
- Rating
- 5/5 (264)
- Duration
- 8 hours
- From
- $125 per person
• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through the scenic Chianti wine region and explore the medieval gems
What you get
About this experience
• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through the scenic Chianti wine region and explore the medieval gems of Siena, San Gimignano. Visit iconic sites such as Piazza del Campo in Siena, famous for the Palio horse race, stroll among the medieval towers of San Gimignano (UNESCO site), and soak in the authentic atmosphere of the Tuscan countryside. Upgrade your experience with an optional wine tasting or an optional traditional lunch at a local organic farm or winery. • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the winery by your guide • Taste Craft Chianti Classico wine at a local vineyard (option) • Hotel or private address pick-up & drop-off Perfect for couples, families, and small groups looking for a relaxed, authentic, and fully private Tuscany experience.
What travelers are saying
Outty’s summary of the themes that recur across 264 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
7 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
6 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.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Traveler reviews
264 verified traveler reviews for Private Day Trip Siena, San Gimignano and Chianti from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Excellent Tuscany Tour with Alessandro
Alessandro was an amazing guide for our day in Tuscany - prompt, engaging, funny, informative - he was great. Our tour was terrific. Highly recommend UniqueTuscany tours.
via Tripadvisor
Day trip to Toscany
He gave us a great experience. He explained what we were looking at as he drove us to to the different places. He was very accommodating and helpful.
via Tripadvisor
Absolutely amazing!
Everything about this day trip was outstanding and flawless, from the communication and pick up to exploring Tuscany and our return back to Florence. Alessandro is so knowledgable about Florence and Tuscany and he provided in great detail about history and culture. He was an excellent transfer and guide and I hope we will return again soon! This is a must-do!
via Tripadvisor
It was a highlight of our trip to Italy and Alex was fantastic!
Pickup and logistics were flawless. He recommended the Wine Tasting and lunch which were fantastic. We had the Mille Miglia going on the same day which caused a little traffic but added to the whole experience. Alex gave us plenty of time at the various stops. No feedback at all. While it was a little pricy, it was money very well spent. His van was very nice and comfortable for our family.
via Tripadvisor
Memories for a lifetime with Alex's help!
The trip was absolutely amazing with memories for a lifetime! Alessandros made some attritional recommendations that were wonderful, and provide my family memories and joy or quite some time. Alex was so knowledgeable and kind, he provided us with so much useful information/history/culture and not just a ride. Thank you so much, would highly recommend this trip and Alessandros (Alex) as your guide and driver.
via Viator
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
- 92
- Verdict
- Exceptional
Why this scores 88
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Day Trip Siena, San Gimignano and Chianti from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Day Trip Siena, San Gimignano and Chianti from Florence cost?
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Prices start at $125 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 Day Trip Siena, San Gimignano and Chianti 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 Day Trip Siena, San Gimignano and Chianti from Florence worth it?
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It holds an Outty Ranking of 88 out of 100, which we label "Exceptional". That score blends traveler sentiment (5/5 across 264 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 Day Trip Siena, San Gimignano and Chianti 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 Day Trip Siena, San Gimignano and Chianti 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 Day Trip Siena, San Gimignano and Chianti from Florence?
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Around 92 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 Day Trip Siena, San Gimignano and Chianti 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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