Small-Group Siena and San Gimignano with Dinner in a Boutique Winery

Badge of ExcellenceFirenze, Italy
Likely to Sell Out

From $217.90

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 8 hours (approx.)
  • Mobile ticket
  • Offered in: English


Get a true taste for the Tuscan countryside with this day trip to Siena, San Gimignano and a Chianti winery for dinner. Departing from Florence, venture first to the city of Siena for a guided tour through the Piazza del Campo, the site of the renowned Palio horse races, as well as a surprise food tasting. Afterward, wander the hilltown of San Gimignano before heading to a Chianti winery for a delicious 3-course dinner, complemented by fine local wine. Your trip is reserved to 16 people to keep the experience intimate.
  • Siena and San Gimignano tour with dinner in Chianti
  • Leave Florence and travel through the Tuscan countryside to Siena
  • Take a Siena walking tour around Piazza del Campo and the city’s picturesque streets
  • Make the most of some free time in the hill-town of San Gimignano
  • Visit a Chianti winery at sunset and savor a 3-course meal with wine
  • Small-group experience with a maximum of 16 people ensures personalized attention

What's Included

  • Transport by air-conditioned Mercedes Minivan
  • Professional english speaking guide
  • Siena walking tour
  • Dinner with wine
  • Free Time in San Gimignano
  • Guided visit of the winery cellars and wine tasting
  • Gratuities
  • Hotel pickup and drop-off

Meeting And Pickup

Meeting point

  • Florencetown
    Piazza Mentana, 3, 50123 Firenze FI, Italy

    FLORENCETOWN BOOKING OFFICE, Piazza Mentana 2red FIRENZE (opposite the Arno River). Please be at the meeting point 15 minutes before the scheduled departure time.

Start time

02:00 PM

End point

This activity ends back at the meeting point.

What To Expect

Depart from central Florence and venture into the Tuscan countryside, a beautiful landscape marked by olive groves, green hills and cypress trees.

Arrive first in Siena, one of Tuscany’s crown jewels. Follow a local guide on a walking tour through the city, passing charming backstreets as well as Piazza del Campo, the celebrated main square that hosts the Palio horse races twice a year. Learn about Siena’s contrades, or districts, which each have individual legacies, traditions and anthems. Before departing, sample a surprise local specialty.

Continue to the hilltown of San Gimignano, known for its impressive towers. Relax with some time to roam the streets independently, popping into local shops or admiring the medieval architecture.  

Afterward, travel to a Chianti winery to soak up the sunset while eating dinner. Weather permitting, take a seat outdoors and feast on a 3-course meal of authentic Tuscan dishes with wine.

After a day of food, wine and sightseeing, you will be returned to central Florence.

Piazza della Repubblica (Pass By)

Florencetown Tours & News stand - meeting point

Piazza del Campo

Guided Tour

2 hours Admission Ticket Included

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • RAIN POLICY: The tour runs rain or shine.
  • No-shows will not be refunded.
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • Most travelers can participate
  • This tour/activity will have a maximum of 8 travelers

Cancellation Policy

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

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.

Traveler Photos

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Traveler Tips

A long tour to some very worthwhile hill top places.
86 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 86 reviews
My daughter and I had a...
Heather_S, Jul 2022
My daughter and I had a great experience on this tour. Our guide Rubina was wonderful in all ways- she was very knowledgeable and enjoyed answering our questions. The wine tasting/dinner experience was in our opinion the best part of the trip, definitely something we will always remember.
Siena and San Gimignano are must see, better tour guide needed.
Peter_C, Jul 2022
Siena and San Gimignano are must-see stops as part of your Italy experience. This trips had three parts. The driver was helpful and pointed out interesting sites along the journey. Part One: Siena. Siena is a remarkable city; home of the Palio. Our guide was not a great story teller. If not for our previous knowledge of the city, the Palio, and the neighborhoods, we would not have learned what makes Siena so special. She did not bring excitement about the spectacle of the Palio horse race. Siena is must-see, but a better tour guide is needed. Part Two: San Gimignano. We were left to explore on our own, which is all that is needed in San Gimignano. We only had one hour. 90 minutes to two hours would be better. It would allow you to take in the vista views, sample the local wine, and enjoy some gelato without feeling rushed. Part Three: dinner at winery in Chianti. This was beautiful. Excellent food and wine. And the location was amazing. Overall, this is an excellent tour that could be so much better with some small adjustments. An extra hour in San Gimignano and a better tour guide in Siena.
The lady who took us...
Pavitra_B, May 2022
The lady who took us around Rubina was fantastic. The random group of people in the tour we very friendly. Would recommend it.
A truly valuable experience!
Gabriel_N, Sep 2021
What an amazing tour! Our guide Brando was fantastic. He shared valuable knowledge and did a great job of helping us understand the history and the importance of each of the places that we attended. He even took some extra time and showed us the city at night and it was absolutely beautiful.
sjhfrog, Nov 2019
We felt we spent way too much time in the van. The two guides were definitely knowledgeable and friendly. However, the driver (one of the guides) drove WAY TOO FAST ON THE Highway. It was downright scary. 3 of us commented on the driving, she never slowed down. Tour started at 2:00 and we had a one hour drive ahead of us. We picked up sandwiches to eat in the van on our way and we were told we couldn't eat them. Dinner was scheduled for 8:00 p.m. There was no mention anyway that we would not be able to have a snack or eat in the van. For the price of 170 Euro we didn't feel it was worth it.
Well worth it!
Therese J, Oct 2019
What a fabulous evening. Siena and San Gimignano are just stunning places surrounded by sweeping landscapes. Antonella was lovely and very knowledgeable.
Siena and San Gimignano are "Must See Destinations"
lizscott2019, Sep 2019
A long tour to some very worthwhile hill top places. The historic Medieval towns of Siena and San Gimignano (the second "g" is silent) should not be missed. San G. is small enough to tour without a guide but Siena is larger, more complex and comes alive with the walk around tour narrated by one of the town's proud and knowledgeable citizens. Wish I could remember our guide's name. She was excellent. Comfortable late model Mercedes tour vans. Our driver Andreas was competent, well informed and offered entertaining observations about drivers we encountered along the way. I was co-pilot. Diamonde Winery was lovely but small so tour was cursory. We always buy wine to thank the host for their hospitality. At 32 Euro it should be good. Dinner was fine but too much like home. Lacked that special Italian restaurant dining out appeal we came to expect after a week in Italy. Perhaps if it was served in the Diamonde restaurant and from the menu instead of a back room set up for tours it would have impressed.
Lisa_B, May 2019
We loved, loved, loved, loved this tour! Started with a guided walking tour of Siena - just beautiful and the guide was so interesting and informative. The history of this town is wonderful! Next we visited San Gimignano and it was again wonderful, such a beautiful part of Tuscany. Last stop was a vineyard and dinner (with wines selected to accompany each course). An absolutely wonderful way to spend 8 hours in this gorgeous part of Italy!
Beautiful Day, Beautiful Towns
Christie_H, Aug 2018
It was a beautiful day visiting Siena, San Gimignano, and the Diadema Winery. Marta and Francesca, our guides were very knowledgeable and kind. We loved this trip! -Melissa Hanson, Minnesota, USA
Not what you pay for
Anita P, Jul 2018
Let me start by our 2 guides were great. Then van was noisy we could barely hear our driver. No cooler for cold water. The dinner was at a lovely little vineyard with terrible service and food. We were told cheese plate, pasta (lasagna mentioned) and desert. When we requested “no pork” what we got was farro, string bean soup with a poached egg in it and biscotti with a shot glass of vermouth. After much discussion with the kitchen staff by our guide we ordered from the menu. My flan was frozen solid. Don’t pay for dinner on this trip.
Friend's Trip
Judy_L, Jul 2018
The tour was great, We also did the Cinque Terre Tour with Pesto Making that was OUTSTANDING! We were 16 friends, 8 couples. Thanks for making our trip to Tuscany memorable!
Everything was good. However, it...
Antonio S, Jun 2018
Everything was good. However, it should include getting into the Cathedral in Siena or at least allowing time to people to see it. There was enough time to accommodate that.
What a lovely day we had! There...
BobbiL_M, Oct 2017
What a lovely day we had! There were only 8 of us and the tour of Siena was wonderful. I would have liked a little more time in San Gimignano. Our dinner was just fabulous - the food and the experience! Highly recommend!
This tour was a must see! Our driver...
Karen H, Oct 2017
This tour was a must see! Our driver was very friendly and professional. The town of Sienna was beautiful and rich with history. Our tour guide was very personable and full of information. San Gimignano was also a quint town. Unfortunately it rained while we were there so I don't feel we got the flavor of that town. Speaking of flavor, the Chianti Dinner and wine tasting was fantastic! Delicious food and wine pairings. Bring your appetite and pace yourself! Highly recommend!
This is a very interesting tour with...
yetshunkwan, Aug 2017
This is a very interesting tour with many interesting sites to visit. Siena is a very beautiful town and we have lucky to be there at the preparation day of the Palio di Siena horse race that is held twice each year, on 2 July and 16 August. This atmosphere on the day was really electrifying. I am sure it will even be 10X more electrifying on the actual day itself :- . Be ready for the walk in Siena though. It is quite hilly. San Gimignano is a smaller town than expected but still offer a nice place to visit. The dinner at the end of the tour was a simple one but the wine tasting was great. The dinner also offered the chance to have nice decent amount of chat with different nationalities. Overall it was a nice tour.
Great tour, meal, and wines. I would...
Mell On, Aug 2017
Great tour, meal, and wines. I would have missed Siena otherwise. Ordered wines from the winery that showed up no problem as promised. A really great extension to a stay in Florence.
I was really looking forward to this...
nicolle, Jun 2017
I was really looking forward to this and I was disappointed. Sienna was wonderful and our guide there was very informed and lively. Had we not found a tower in San Gimignano to climb that had beautiful views of the Tuscan countryside it would have just been a tourist shopping stop. The winery was the biggest let down. When you say travel to a Chianti winery to soak up the sunset while eating dinner I would expect to be viewing the sunset while eating. This was not the case. The sunset was down the hill and behind a building from where we ate. The only reason we even caught the sunset was because me and another guest asked about it. And once we were taken down there, the sunset was too far down the horizon to get a could view/picture. The food was good not great but none of it was very warm. In fact the pork with sauce was a bit dry and cold. I don't know how other reviewers got plenty of wine as we only got a tasting of 2- and I mean a tasting. The liquor at the end of dinner was very strong and no one liked it. The driver we had Elisa was sweet and nice. Because of her and the 2 great couples we met on the tour I gave this 3 stars instead of 2. Buyer beware.
Very nice tour to explore 2 of the best...
dangia, Oct 2016
Very nice tour to explore 2 of the best towns in Tuscany! The walking tour in Siena was really good with a local guide and you can hear about the contrade history and then have free time in San Giminiano followed by a dinner in Chianti which was super good! Big portions (appetizers, pasta, meat and dessert!) and lot of wine. Totally recommend if you have only one afternoon to explore the Tuscan countryside!
Christian was a pleasant and...
Sylvie_S, Sep 2016
Christian was a pleasant and entertaining guide who took us to Siena first before San Gimignano. The walking tour of Siena could have been shorter see later in my review why or it could have included more extensive specialty tasting. Either way, San Gimignano is lovely with an award winning gelato shop on the right side through the entrance. Then the drive into deep Tuscany country would have been better if done one hour sooner Siena took too long as we arrived at night end of September to the estate. We missed some photo opportunities. The meal was alright and the tasting very limited to below half a glass each time. The place used to produce wine so your dinner takes place in the cellar room which is inviting. A nice ride over all but the meal and the fact that it was dark at our final destination force me to give it 4 stars only.
Guide was very informative. Did not...
Suchdeep_B, Sep 2016
Guide was very informative. Did not provide guide at San Gimignano. The dinner was more than one hour away from San Gemignano! Dinner seemed to be homemade and delicious