From Florence: PRIVATE Siena and San Gimignano with wine tasting
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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 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is From Florence: PRIVATE Siena and San Gimignano with wine tasting worth booking?
From Florence: PRIVATE Siena and San Gimignano with wine tasting is a 9.5-hour experience in Florence, Italy, from $100 per person. It scores 65 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 65 / 100
- Rating
- 5/5 (6)
- Duration
- 9.5 hours
- From
- $100 per person
Discover 3 of the most authentic towns nestled in the heart of the tuscany countryside. Siena, the famous Palio city, San Gimignano, UNESCO heritage and Monteriggioni, one of the most enchanting Italian walled town. Ta
What you get
- Guided Wine tasting
- Luxury car or premium van at disposal
- Free time in all the cities
- Private tour
- Lunch
- In-vehicle air conditioning
About this experience
Discover 3 of the most authentic towns nestled in the heart of the tuscany countryside. Siena, the famous Palio city, San Gimignano, UNESCO heritage and Monteriggioni, one of the most enchanting Italian walled town. Taste local wine, including the DOC Tuscanian white wine! "Explore the essence of Tuscany:Siena, San Gimignano and Monteriggioni are waiting to be discovered!!!" WHY CHOOSE US? Secure bookings, Guaranteed Departures!
What's included
Included
- Guided Wine tasting
- Luxury car or premium van at disposal
- Free time in all the cities
- Private tour
- Lunch
- In-vehicle air conditioning
- Professional guide in Siena
Not included
- Hotel pickup and drop-off
- Gratuities
What you'll see and do
Florence
The tour starts on board of a premium minivan with an English-speaking driver, air conditioner and free water.
Pass by without stopping
Siena
The first stop is Siena: here you will be welcomed from a local guide that will lead you for 1 hour through the most tipical spots such as Piazza del Campo, Piazza del Duomo where you can appreciate the authentic medieval atmosphere which makes this town special and unique. After that you will have an hour of free time that you can spend to visit the Duomo, do some shopping or simply enjoy the local deliciousness!
120 minutes here
Castello Monteriggioni
Back to our minivan we will bring you to the lovely town of Monteriggioni. Built in 1213, its fame was so big that also the great poet Dante Alighieri makes sign to his round enclosure in the Divin Comedy. There, finally, you will have the chance to try an amazing lunch and local wine in a great location!
90 minutes here · Admission included
San Gimignano 1300
On the route to San Gimignano, you will enjoy the beautiful Chianti landscape, plenty of vineyards and olive groves. At the arrival, you will have free time to discover "The city of beautiful towers" that has been nominated heritage of UNESCO as example of medieval town.
90 minutes here · Admission included
San Gimignano
Wine tasting in a local winery, You will learn about the wine making process: the vineyard techniques , the wine making process, its ageing and ,off course, how to appreciate it by drinking different wines! ..and local olive oil!
75 minutes here
Florence
At the end of the visit, come back to Florence in full comfort just in time for the sunset!
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
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Keys Of Italy / Florence
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Not recommended for travelers with spinal injuries
- Suitable for all physical fitness levels
- A maximum of 8 people per booking
- A minimum of 2 people per booking is required
- No minimum age required
- Children must be accompanied by an adult
Photos
What travelers are saying
Outty’s summary of the themes that recur across 6 traveler reviews. Written by us, not quoted from reviewers.
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.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
6 verified traveler reviews for From Florence: PRIVATE Siena and San Gimignano with wine tasting. Ratings and reviews provided by Viator and Tripadvisor.
Great tour a family with 3 boys
Karim our guide and driver was amazing. This tour was tailored to us and our family, with 3 boys obsessed with the Assasins Creed game. We spent a lot of time in Monteriggioni and my kids loved it. Siena was very interested and beautiful as was San Gianmgno. Great tour and the way to go with kids.
Response from the operator: Thank you very much for you feedback, hearing your appreciation makes us very happy and proud of what we're doing, sharing the love for our beautiful country! Hope to see you in the future in any of our Italian destination! Regards, KEYS OF ITALY team
via Viator
Private Tour of Siena, San Gimignano and Monteriggioni
This was our second private tour with CiaoFlorence. We were so excited to have Elvis as our personal guide again!! Elvis was very flexible, professional and entertaining. The tour was scheduled for eight hours but we were getting back to early so Elvis planned a few surprise stops to make sure we got the most of our trip. We couldn’t have had a better day or guide!! Will book again with CiaoFlorence and request Elvis in a heartbeat. You know your guide is great, when you end up taking selfies together!
Response from the operator: Thank you very much for you feedback, hearing your appreciation makes us very happy and proud of what we're doing, sharing the love for our beautiful country! Hope to see you in the future in any of our Italian destination! Regards, KEYS OF ITALY team
via Tripadvisor
Lovely way to discover the real tuscany
I really want to recommend this tour because for us has been perfect.. The driver Luca was helpful and friendly with us explaining everything while he was driving. We have had a local guide in Siena called Maria whom was very knowledgeble and careful with our needs. At lunch time we went to a local restaurant in Monteriggioni where the chef showned us different kinds of flours and also the way to make "pici", typical pasta from tuscany. At San Gimignano don't miss the gelato which is the best I've ever had!!!
Response from the operator: Dear customer, Many thanks for your kind feedback! We are really glad to hear that you enjoyed our tour and we hope to see you again in Florence. Have a great day! Keys of Italy team
via Viator
A perfect day trip...
I was in this tour with my partner and on the minivan we were travelling there was just another family of 4 people. The guide Anna in Siena was very knowledgeble and ,with her, has been easy walking through the city center. The lunch in the typical "trattoria" was really good and the homemade pasta simply amazing!!! In San Gimignano we have had 2 hours of free time where we have been advised to try the awarded "best ice cream in the world"...delicious!! UZ
Response from the operator: Dear customer, Many thanks for your kind feedback! We are really glad to hear that you enjoyed our tour and we hope to see you again in Florence. Have a great day! Keys of Italy team
via Viator
Loved it!
It was just 4 of us, which was comfortable in the van. The driver was not a tour guide, we had tour guides at the stops. The wine and lunch was good.
via Viator
Good to know
- Duration
- 9.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $100 to $556
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 2
- Verdict
- Solid Choice
Why this scores 65
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
From Florence: PRIVATE Siena and San Gimignano with wine tasting: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does From Florence: PRIVATE Siena and San Gimignano with wine tasting cost?
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Prices start at $100 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 From Florence: PRIVATE Siena and San Gimignano with wine tasting take?
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Plan for about 9.5 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 From Florence: PRIVATE Siena and San Gimignano with wine tasting worth it?
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It holds an Outty Ranking of 65 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 6 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 From Florence: PRIVATE Siena and San Gimignano with wine tasting?
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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 From Florence: PRIVATE Siena and San Gimignano with wine tasting suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 9.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book From Florence: PRIVATE Siena and San Gimignano with wine tasting?
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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 9.5-hour experience runs outdoors or after sunset.
Where does From Florence: PRIVATE Siena and San Gimignano with wine tasting 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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