
Chianti and San Gimignano - 2 Wineries with Pairing Lunch
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 84 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Chianti and San Gimignano - 2 Wineries with Pairing Lunch worth booking?
Chianti and San Gimignano - 2 Wineries with Pairing Lunch is a 6-hour experience in Florence, Italy, from $229 per person. It scores 73 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.9/5 rating across 84 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 73 / 100
- Rating
- 4.9/5 (84)
- Duration
- 6 hours
- From
- $229 per person
Our driver guide will collect you at the designated meeting point, setting off toward the heart of Chianti Classico. Experience a 1-day exciting trip in the heart of Chianti and visit the most beautiful village in the re
What you get
About this experience
Our driver guide will collect you at the designated meeting point, setting off toward the heart of Chianti Classico. Experience a 1-day exciting trip in the heart of Chianti and visit the most beautiful village in the region. > Step 1 - Charming boutique winery in Chianti > Step 2 - Visit of Monteriggioni and/or San Gimignano > Step 3 - Pairing lunch in the most famous winery in the area Tour Length: 7/8 hours. Departure Time: From Florence 9.00 AM Note: During this excursion, transport will be made in a Mercedes 8-seat minivan, which offers maximum comfort, with air-conditioning, large panoramic windows, and comfortable seats. Unless you don't specify you want to remain private, it is possible to be joined with some other people in the party ( maximum 1 van ) Popularity: ***** (best seller wine and food tour in Tuscany)
What travelers are saying
Outty’s summary of the themes that recur across 84 traveler reviews. Written by us, not quoted from reviewers.
The guide
7 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
6 mentionsThe tastings and food stops are a highlight for most reviewers.
Photo opportunities
3 mentionsThe views and photo stops come up again and again.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Organization
2 mentionsPickup, timing, and logistics are described as running smoothly.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Traveler reviews
84 verified traveler reviews for Chianti and San Gimignano - 2 Wineries with Pairing Lunch. Ratings and reviews provided by Viator and Tripadvisor.
Laidback and Amazing Experience
Had an amazing experience with Leonardo. Very personal tour, got to know a lot about the country and Tuscany, and felt very chill and welcoming. Would highly recommend to anyone who wants a carefree way to see the Tuscan countryside. Easily one of the best experiences we’ve had on our vacation!
via Tripadvisor
Outstanding experience
Our Driver/Guide Camilla was outstanding in every way. We’ve had several driver guides from Tours of Tuscany and all were fantastic. Mihai and Stefan were also great. Tours of Italy rocks - well worth it.
via Tripadvisor
1st Class experience
We had a first-class experience on the Siena, San Gimignano & Winery tour with Niccolo and Tours of Tuscany. From start to finish, everything exceeded our expectations. Our host was warm and welcoming, and the guides were knowledgeable, friendly, and passionate about the region. The personalised service, excellent wines, and breathtaking scenery made for an unforgettable day. We highly recommend this tour to anyone looking for a memorable Tuscan experience!
via Tripadvisor
Breathtaking Day, Bountiful Food & Wine, and Beguiling Guide
Our guide Camila picked us up right on time with a smile on her face and a warm hug for all of us. We had a breathtaking drive through the Tuscan countryside, where Camila regaled us with amazing facts about the region the wines, places we were going, the process of wine making, and many other interesting facts. We arrived at the first winery where our guide took us on a tour through the fields, the cellar and the grounds, while describing the process of winemaking bottling and the family who’s owned the winery for five generations. In beautiful lunchroom, but we tasted some of the most amazing wines we’ve ever had which were paired with some delicious cheeses, meats, and bread. We then made our way to San Gimignano where we walked through the beautiful medieval streets, shopped and had delicious gelato. After this, we went onto the second winery where we continued our culinary extravaganza with more delicious wine and amazing food. Finally, it was time to drive home. I would highly recommend this tour and we can’t say enough about Camila, our amazing tour guide and now friend.
via Tripadvisor
Great experience!
Had an amazing day tasting wine and getting to see more of the countryside! Our driver Camilla was excellent!
via Tripadvisor
Good to know
- Duration
- 6 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Booked in 30 days
- 29
- Verdict
- Strongly Recommended
Why this scores 73
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Chianti and San Gimignano - 2 Wineries with Pairing Lunch: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Chianti and San Gimignano - 2 Wineries with Pairing Lunch cost?
+
Prices start at $229 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 Chianti and San Gimignano - 2 Wineries with Pairing Lunch take?
+
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 Chianti and San Gimignano - 2 Wineries with Pairing Lunch worth it?
+
It holds an Outty Ranking of 73 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 84 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 Chianti and San Gimignano - 2 Wineries with Pairing Lunch?
+
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 Chianti and San Gimignano - 2 Wineries with Pairing Lunch suitable for kids and families?
+
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 Chianti and San Gimignano - 2 Wineries with Pairing Lunch?
+
Around 29 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?
+
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 Chianti and San Gimignano - 2 Wineries with Pairing Lunch start and how do I get there?
+
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?
+
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?
+
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?
+
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?
+
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.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for Chianti and San Gimignano - 2 Wineries with Pairing Lunch.
Pick your date




