
Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano
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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
4.8/5
Based on 72 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano worth booking?
Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano is a 6-hour experience in Florence, Italy, from $81 per person. It scores 74 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.8/5 rating across 72 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 74 / 100
- Rating
- 4.8/5 (72)
- Duration
- 6 hours
- From
- $81 per person
Visit two Tuscan wineries without having to worry about designating a driver by opting for this tour that includes transportation. Immerse yourself in the Chianti wine region as you sample a variety of wines. Discover th
What you get
About this experience
Visit two Tuscan wineries without having to worry about designating a driver by opting for this tour that includes transportation. Immerse yourself in the Chianti wine region as you sample a variety of wines. Discover the art of winemaking through tastings while enjoying the scenery of the Tuscan countryside. Then head to San Gimignano to spend some time exploring its medieval ramparts.
What's included
Included
- Our English-speaking tour guide
- Free time in San Gimignano
- Visit 2 Wineries
- Alcoholic beverages
- In-vehicle air conditioning
- Views of the Chianti wine region sourrounding San Gimignano
- Snacks
Not included
- Gratuities
What you'll see and do
Your experience begins depending on the option you selected at the time of booking , either from our headquarters, Tuscany on Wheels (located just few km outside San Gimignano with free car parking available), or directly from San Gimignano.
15 minutes here · Admission included
Tuscany
First, we’ll visit a winery an hour outside Florence to taste 5 wines, including Chianti Classico, Vernaccia, and Super Tuscan. We’ll also sample a 30-year-old balsamic vinegar, plus truffle extra virgin olive oil. Learn to recognize different flavors and refine your palate with a passionate wine producer. Fun and new skills are guaranteed!
90 minutes here
Ulignano
Next, we’ll visit a local winery in a beautiful area known for D.O.C.G. Vernaccia white wine, overlooking the towers of San Gimignano. The winemakers will guide you through vineyards and cellars, sharing secrets of wine and oil production, and the best wine and food pairings. Enjoy three wines: Vernaccia white, rosé, and Chianti Colli Senesi D.O.C.G. You can also purchase local products and wine at great prices to take home or ship to friends and family.
90 minutes here
Historic Centre of San Gimignano
The trip isn't over yet as you just earned a bonus stop in San Gimignano for a little stroll before making your way back. You can't miss San Gimignano when you visit Tuscany! San Gimignano is known for its 14 medieval towers, which dominate the skyline and create a unique atmosphere. These towers were built by wealthy families as symbols of their power and status, and today they are one of the town’s main attractions. You can climb to the top of some of the towers and enjoy stunning views of the surrounding countryside.
90 minutes here
The tour concludes at around 4:30 pm at the Tuscany on Wheels office, where you’ll return with wonderful memories, a camera full of photos, and a few new friends. If you selected San Gimignano as your departure point, you have the option to end your tour there instead, at approximately at 2:30 pm, rather than returning to the main office.
30 minutes here
Where it starts and ends
Meeting point
Florence
We meet on Via di San Gimignano, at the "Bivio Volterra" bus stop, located right next to the roundabout that connects to Via Baccanella.
Meeting point
Florence
We meet at our Tuscany on Wheels office located on Strada di Sant'Appiano 9/I right at the exit Poggibonsi Nord of the speedway Florence - Siena , 12km to San Gimignano. Park your car by the office for free or request a pick up.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
We meet on Via di San Gimignano, at the "Bivio Volterra" bus stop, located right next to the roundabout that connects to Via Baccanella.
Ends at
We meet at our Tuscany on Wheels office located on Strada di Sant'Appiano 9/I right at the exit Poggibonsi Nord of the speedway Florence - Siena , 12km to San Gimignano. Park your car by the office for free or request a pick up.
Options you can book
From Tuscany on Wheels
Small Group Tour: from Tuscany on Wheels office in Chianti Starting point: Tuscany on Wheels - Tours in & from San Gimignano, Strada di Sant' Appiano, 9/i, 50028 Barberino Tavarnelle FI, Italy
From San Gimignano
Small Group Tour: From San Gimignano Starting point: Bivio Volterra, 53037 San Gimignano, Province of Siena, Italy
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
- Italy on a Budget tours
Know before you go
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Photos






What travelers are saying
Outty’s summary of the themes that recur across 72 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
8 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
5 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Traveler reviews
72 verified traveler reviews for Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano. Ratings and reviews provided by Viator and Tripadvisor.
Tuscany tour with the best views
Dario was amazing! The views on this tour at the second winery are unmatched. We loved seeing the rolling hills and meeting the farm animals. Walking through the wine production at such a detailed level was incredible. We live close to Napa Valley and have never experienced this level of a detailed walkthrough. Exploring San Gimignano is a must see. Seeing such a preserved medieval village is a once in a lifetime experience. We did 2 wine tours from Florence with different companies and this one took the cake.
Response from the operator: Thank you so much for your incredible review! We’re thrilled that your tour leader Dario made the experience so special and that you enjoyed the breathtaking views, the farm animals, and the detailed look into the wine production process. Your comparison to Napa Valley means a great deal to us. San Gimignano truly is unforgettable, and we’re honored that this tour was the highlight of your wine experiences from Florence. We hope to welcome you back to Tuscany again soon!
via Tripadvisor
Best wine tour ever!
Incredible tour, amazing wine, and San Gimiagno was so cool to see!
Response from the operator: Thank you so much! We’re delighted you enjoyed the tour, the amazing wine, and the beauty of San Gimignano. We hope to welcome you back for another unforgettable experience in Italy!
via Tripadvisor
Tuscany wine tours
Dario was an absolutely superb guide, he provided us with great historical data from the local area and what to expect during our wine tours. He was extremely professional and friendly.
Response from the operator: Thank you so much for your wonderful review! We’re delighted to hear that Dario, your tour leader, made the experience so enjoyable with his professionalism, friendliness, and knowledge of the local area. It’s great to know that his explanations helped you understand more about the region and what to expect during the wine tours. We’ll be sure to pass along your kind words to him, and we hope to welcome you back to Tuscany again soon!
via Tripadvisor
Great way to experience wine country
So nice to be out in gorgeous wine country sampling all the best it has to offer. Wine and balsamic selection was both diverse and quality. Ned, our driver was knowledgeable and charismatic. I asked several questions and he was able to answer most of them. Good guy, happy to be in his van. San Gimigiano was surprisingly delightful. It offered something different than Florence and Rome, way worth the extra stop. Highly recommend the tour. Just be prepared for a long, sleepy drive home though.
Response from the operator: Thank you so much for your wonderful review! We're delighted to hear you enjoyed exploring the beautiful Tuscan countryside, tasting the wines and balsamic, and discovering the charm of San Gimignano. We'll be sure to share your kind words with your tour leader Nedas and he'll be happy to know his knowledge and enthusiasm made your day even more enjoyable. Thank you for your recommendation, and we hope to welcome you back to Tuscany again soon!
via Tripadvisor
Perfect wine tour!
Alex was the best! We had an amazing experience wine tasting in Tuscany! He went above and beyond explaining the history of San Gimignano. Definitely recommend this tour!
Response from the operator: Thank you so much for your fantastic review! We’re delighted to hear that you had such an amazing wine tasting experience in Tuscany with your tour leader Alessandro. It’s wonderful to know that his passion and knowledge, especially when sharing the history of San Gimignano, helped make your day even more special. Thank you for your recommendation, and we hope to welcome you back for another unforgettable adventure in Italy soon!
via Tripadvisor
Good to know
- Duration
- 6 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $81 to $149
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 25
- Verdict
- Strongly Recommended
Why this scores 74
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano cost?
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Prices start at $81 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 Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano 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 Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano worth it?
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It holds an Outty Ranking of 74 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.8/5 across 72 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 Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano?
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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 Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano 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 Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano?
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Around 25 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 Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano 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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