
San Gimignano & Chianti Small Group Wine Tour
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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 2 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is San Gimignano & Chianti Small Group Wine Tour worth booking?
San Gimignano & Chianti Small Group Wine Tour is a 6-hour experience in Florence, Italy, from $180 per person. It scores 56 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 2 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 56 / 100
- Rating
- 5/5 (2)
- Duration
- 6 hours
- From
- $180 per person
This small-group experience blends the iconic towers of San Gimignano with a personally hosted winery lunch at a family-run Chianti estate. Rather than rushing between multiple stops, the tour focuses on quality time in
What you get
- Tour and lunch \ wine tasting with experienced wine operator
- Alcoholic beverages
- Lunch
- English speaking driver tour escort
- In-vehicle air conditioning
About this experience
This small-group experience blends the iconic towers of San Gimignano with a personally hosted winery lunch at a family-run Chianti estate. Rather than rushing between multiple stops, the tour focuses on quality time in each location, combining medieval history, scenic countryside drives, and an immersive wine and food experience in an intimate setting limited to maximum 8 guests.
What's included
Included
- Tour and lunch \ wine tasting with experienced wine operator
- Alcoholic beverages
- Lunch
- English speaking driver tour escort
- In-vehicle air conditioning
Not included
- Gratuities
What you'll see and do
San Gimignano
Discover San Gimignano, the UNESCO-listed medieval hill town famous for its striking skyline of stone towers. Once a prosperous stop along the Via Francigena pilgrimage route, San Gimignano became known for the powerful families who built defensive towers as symbols of wealth and status. Today, its preserved 13th-century streets, historic squares, and panoramic countryside views make it one of Tuscany’s most iconic destinations.
120 minutes here
Madonna di Pietracupa
As you travel through the heart of Chianti Classico, enjoy scenic views of rolling vineyards, olive groves, and stone farmhouses that define the Tuscan landscape. Passing near the historic area of Madonna di Pietracupa and the hilltop village of San Donato in Poggio, you’ll experience the authentic rural setting that has shaped local wine production for centuries.
Pass by without stopping
San Donato in Poggio
Experience a guided visit at Local a family-run estate in the heart of Chianti Classico. After exploring the vineyards and cellar, enjoy a seated tasting of estate wines that reflect the character of the local terroir. The experience includes a traditional Tuscan lunch featuring a generous platter of cured meats and cheeses, served with estate-produced extra virgin olive oil and aged balsamic vinegar, paired with selected wines in a relaxed countryside setting.
90 minutes here
Where it starts and ends
Meeting point
Florence
Meeting point in the parking area in front of the American Consulate. Our driver will be holding at the meeting point holding our company banner sign.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Meeting point in the parking area in front of the American Consulate. Our driver will be holding at the meeting point holding our company banner sign.
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
- Mon
- Group size
- Up to 8 travelers per booking
- Operated by
- Tuscan Travellers
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
- Suitable for all physical fitness levels
- Driver tour escort will introduce you to the destinations, they will knot guide you in churches, museums, archeological sites.
Photos






Traveler reviews
2 verified traveler reviews for San Gimignano & Chianti Small Group Wine Tour. Ratings and reviews provided by Viator and Tripadvisor.
Yaris incredible tour guide!!!
Our family recently returned from a 14‑night journey through Italy. The trip flowed beautifully from start to finish. We traveled through Rome, Florence, Pisa Venice, Milan, and Lake Como and more. Our favorite place was Florence. Yaris our tour guide was amazing!!! His guidance of understand history and all the events that made the wonderful and rich culture of Florence, Chianti area, Siena and St. Gimignano. We also had great converstaions about history, food, science and remarks of all towns we visited. The tour experience with Yaris was incredible!!! We will be back and defintly looking forward to book with Yaris again.
Response from the operator: We're so happy you enjoyed your Italian experience, and we're even more pleased to hear you enjoyed the Tuscan experience with our Yaris guide. We look forward to seeing you again in the future for other memorable destinations. Thank you.
via Tripadvisor
Amazing from start to finish
Our driver Claudio was informative and fun. Very professional and kind. The overall experience was wonderful. This was not my first time to San Gimignano but was by far the best. The winery, tasting and the lunch that was prepared by the mom (Owners) was delightful and our hostess for the tasting, Lucia, made the entire experience one to remember. A high recommendation!! 5 stars!!
Response from the operator: Thank you so much for your positive review of the tour and the driver/guide who accompanied you. We look forward to seeing you again in the future for other excursions. Thank you.
via Viator
Good to know
- Duration
- 6 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Mon
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 1
- Verdict
- Worth a Look
Why this scores 56
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
San Gimignano & Chianti Small Group Wine Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does San Gimignano & Chianti Small Group Wine Tour cost?
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Prices start at $180 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 San Gimignano & Chianti Small Group Wine Tour take?
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Plan for about 6 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 San Gimignano & Chianti Small Group Wine Tour worth it?
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It holds an Outty Ranking of 56 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 2 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 San Gimignano & Chianti Small Group Wine Tour?
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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 San Gimignano & Chianti Small Group Wine Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 6-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book San Gimignano & Chianti Small Group Wine Tour?
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Around 1 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 6-hour experience runs outdoors or after sunset.
Where does San Gimignano & Chianti Small Group Wine Tour 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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