Chianti and San Gimignano - 2 Wineries with Pairing Lunch

Recommended by 99% of travelers

Florence, Italy

6 to 8 hours (approx.)
Mobile ticket
Offered in: English

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Overview

When visiting Florence (or Siena), spend a delicious day winery hopping in the renowned Chianti wine region. Visit two of the best estates for tastings of Chianti Classico and other top varietals, and enjoy a gourmet lunch of Tuscan specialties. There's also time to soak up countryside culture and history with a stop in San Gimignano or Monteriggioni, two of the best-preserved medieval towns in Tuscany.

Experience the best of Tuscan wine country without renting a car
Visit two hand-picked wineries for guided tastings and a lunch of local products
Get a glimpse into medieval Tuscany with a stop in San Gimignano or Monteriggioni
Round-trip transport from Florence, Siena, and the Chianti region

What's Included

2 Winery tour and tasting
Lunch with wine pairing in a famous Chianti Winery
Pick up and drop off at the designated meeting point
English speaking Driver-guide for the day at disposal
Bottled water
Air-conditioned vehicle

Gratuities

Meeting and Pickup

Meeting point

Florence National Central Library
Piazza dei Cavalleggeri, 1, 50122 Firenze FI, Italy
Tours of Tuscany Mercedes van

End point

This activity ends back at the meeting point.

Itinerary

Strada Statale 222 Chiantigiana

1 hour • Admission Ticket Included

Historic Centre of San Gimignano

1 hour • Admission Ticket Included

San Gimignano

2 hours • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Stroller accessible
Infant seats available

Not recommended for pregnant travelers
Most travelers can participate
This tour/activity will have a maximum of 8 travelers

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

John_B

What a wonderful and unforgettable day in Tuscany. Stefan picked us up near our hotel in Siena in his spacious, comfortable van and with two other couples set out on a day we will not soon, if ever forget. Stefan knew all the back roads with all the amazing views as we set out to the first of two wine tastings. Then we were off to San Gimignano where we had plenty of time to enjoy that beautiful hill town. Our final tasting and lunch outside in the Tuscan sunshine was just incredible. My wife and I have done a number of tours through Viator and this one ranks at the top. Cannot recommend too highly.

Reviews

4.9

based on 83 reviews

Total reviews and rating from Viator & Tripadvisor

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Sort by: Most insightful

Unforgettable Day in Tuscany

John_B, Sep 2025

Do not miss this! Perfect day.

Holly_A, Apr 2025

My husband and I took this tour and it did not disappoint! We had the most amazing day. Stefan from Tours of Tuscany picked us up in a beautiful clean van with bottles Of water for us and we had a wonderful conversation until we got to our first destination, which was a beautiful private small winery. The scenery on the way was so spectacular and our tasting at the winery was amazing, we walked through the production process, strolled their gorgeous grounds and sat for a wonderful tasting and wound up ordering wine to be shipped to our home. The tour guide was very sweet and very knowledgeable, regrettably-I can’t remember her name. She even took the time to write down some suggested restaurants for us in Siena where we were staying. Then we got back into the van where we went to spend time in gorgeous San Gimignano. We walked around at our leisure and sat and had espresso, it was picture perfect and a must see place in Tuscany-it is like stepping back in time. Finally, we went to another winery which was a little larger and more well-known. The lunch we were served was absolutely delicious and plentiful! . Everything was set so elegantly Luca, our host, was engaging, extremely knowledgeable and passionate about the winery. We bought even more wine! We sat and ate, tasting, many wines and at no point during the tour did we feel rushed. Stefan patiently waited for us to enjoy our experience and then drove us back to our starting point. This will be a forever memory for us. Do not miss this experience. .

Best experience, would recommend to anyone!!!

Sidney_L, Oct 2024

This was such a great experience to see the vineyards and taste the wine of Chianti. We absolutely love love loved our driver and tour guide who made our day completely amazing and special. Thank you to you, Camilla!!! She answered all of our questions about living here as a local, what her life is like, about Italian culture and language, and of course about the wineries and wines. She even helped us book a taxi for our next day transportation. She was FABULOUS!!!! The vineyard and winery we visited were very nice. The food was great, and the wine was better!! Visiting San Gimignano was also really cool to see and definitely worth the stop.

Wine Tour

Jennifer_H, Aug 2024

We had a great day and loved San Gimignano! Our driver was fantastic and taught us so much about local history and wine!

Winery tour

Rebecca_W, Jul 2024

We had an amazing day. Stephan was a wonderful guide and we absolutely loved everything about the day. San Gimignano was beautiful and we had just the right amount of time to explore. The wineries were both very different and we loved them both. I would highly recommend this tour and guide!

I love chianti!

Carol_I, Jul 2024

Our tour leader was amazing and knew so much about the entire area. The two wineries visited were different and gave is a true feel for the land, wine, and operation.

Great way to spend a Tuscan day!

Debra_A, May 2024

Our guide, Stefan, was wonderful: profession and personable. Very much enjoyed the whole experience. Lunch was so more than expected. Great food and wine!

Super great tour

Cindy_W, Oct 2023

Our driver and tourguide Keeko was terrific—-knowledgeable and safe driver. Host for the tasting w lunch was amazing. Winery choices all excellent. Gorgeous scenery…what we anticipated for Tuscany.Would highly recommend this tour for all ages. Beware winding roads and some rough terrain if your prone to motion sickness.

Not worth the money

Scott_R, Sep 2023

When we booked this tour was to visit 3 wineries. Our ticket showed up saying 2. Said our driver would take us down chanti road and explain history. Our driver looked like he just rolled out of bed, wearing jeans and shirt he slept in. Rather than telling us about the area, he texted while driving, and looked at photos that someone sent him. Our 2 hour free time in San Gimignano was 25min granted there was a LOT of traffic so it took a while to get to the town. We couldn’t get the worlds best gelato due to the long line and again we had to be back in the van in 25 min, which you barely got to the store let along wait in line. We got to the second winery and we’re rushed through the tastings. They poured 3 glasses at a time. Served the food and told to tastes each wine with each thing on your plate. They came back to clear plates and to pour the next three glasses. They told us to empty the glass so they could pour the next ones…. This was supposed to be relaxing and pairing but they rushed us. The last wine was a rose. The lady next to me didn’t finish or empty the glass prior and the server just poured the rose over her red! We were the only people in the tasting at the time and we couldn’t figure out why they were rushing our group of 7. They had a large group come in before we were finished and that is why they were rushing us. The wine was good but so not worth the money and so not like the utube video about the tour. It was nothing like they said in the details.

A Must Do in Tuscany

Lauren_M, Apr 2023

My husband and I had a great time on our wine tour. One of our drivers Niccolo was very kind and funny; he drove out of his way to pick us up which we really appreciated. We especially enjoyed the first two wineries; the wine and food were excellent as was the ambiance. The last place where we ate for lunch seemed unprepared for us but the food and wine were good. Just wish we could have sat outside on a beautiful day. Also wish we could have stayed a little longer in each place. Overall we really enjoyed the experience and would recommend it.

Great tour of several very different wineries. Comfortable and informative.

Christine_S, Oct 2021

I have to say that my favorite part of this spectacular tour was meeting Sella at Monte Chiaro winery in Monteriggioni. Not only are the wines here outstanding but her love of wine, and regional foods are unmatched. She brings the wines to life with her presentation skills and we were sad to leave her. Sella says that "wine is food" and full of vitamins and nutrients. So, she has confirmed for me that wine for breakfast is a perfectly good way to start the day!

Fabulous!

Daniel_K, Sep 2021

This was a GREAT tour! Niccolo is an excellent guide and really cares about his guests and wants them to have the best experience. He talked to us about the region, history and scenery the entire ride. The van was comfortable and the wineries he chose were edited in a great way: female owned, historic with tombs from 6 Century BC and agritourismo. Could not have been better!

More than we expected!

Mathieu_D, Aug 2020

We went with my girlfriend to visit the 3 wineries with Niccolò, he was on time to pick us up at our hotel and drived perfectly. On the way he told us numerous stories about Tuscany. The 3 wineries were different from each other, from the small family winery to the third which is more like a deluxe one, where we had a fantastic lunch. We highly recommend the experience!