Recent Searches

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

star-4.577 Reviews
Badge of Excellence
Firenze, Italy
Small-Group Siena and San Gimignano with Dinner in a Boutique Winery

Select Date and Travelers

Number of travelers
1 Adult2 Adults3 Adults4 Adults5 Adults6 Adults7 Adults8 Adults0 Children1 Child2 Children3 Children4 Children5 Children6 Children7 Children8 Children0 Infants1 Infant2 Infants3 Infants4 Infants5 Infants6 Infants7 Infants8 Infants
Free cancellation
Up to 24 hours in advance. Learn more
Loading available options...

Safety measures
icon8 hours  (Approx.)
Mobile ticket
iconOffered in: English
Good for avoiding crowds


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
Saved to wishlist!
Transport by air-conditioned Mercedes Minivan
Professional english speaking guide
Siena walking tour and suprise food tasting
Dinner with wine
Free Time in San Gimignano
Guided visit of the winery cellars and wine tasting
Free subscription to our Food&Wine Club, to access special discounts online on wine&typical products
Hotel pickup and drop-off

Departure Point

Piazza Mentana, 3, 50123 Firenze FI, Italy

FLORENCETOWN BOOKING OFFICE, Piazza Mentana 2red FIRENZE (opposite the Arno River).

Departure Time

2:00 PM

Return Details

Returns to original departure point
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.
Pass By:  
Piazza della Repubblica
Florencetown Tours & News stand - meeting point
Stop At:  
Piazza del Campo
Guided Tour
Duration: 2 hours 
Admission Ticket Included
Stop At:  
Historic Centre of San Gimignano
Free time in San Gimignano, UNESCO Heritage Site
Duration: 1 hour 
Admission Ticket Free
Stop At:  
Relais Villa Olmo
Gourmet Dinner in a Boutique Winery in Chianti
Duration: 1 hour 
Admission Ticket Included
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • The tour runs rain or shine (but please see below).
  • The tour will never be cancelled due to rain.
  • Guest options on rainy days:
  • No-shows will not be refunded."
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • Travelers should have a moderate physical fitness level
  • IMPORTANT We inform all our guests that from August 06th 2021 every European Community citizens must show the Green Pass, as well as a document of recognition at the entrance of the main Italian monuments and museums as well as every indoor bar and restaurant For guests arriving from outside Europe it will be required: a document of recognition a proof of Covid vaccination, or the negative result of the Covid test 48 hrs prior the museum entrance. Those who do not possess the above mentioned documents will NOT be able to enter. No exceptions or refund will be made.
  • This tour/activity will have a maximum of 8 travelers
  • OPERATED BY Florencetown
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.

Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the policy on face masks and attendee health during Small-Group Siena and San Gimignano with Dinner in a Boutique Winery?
A:The policies on face masks and attendee health are:

  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Face masks provided for travelers
See all safety measures taken by Small-Group Siena and San Gimignano with Dinner in a Boutique Winery.
What is the policy on sanitization during Small-Group Siena and San Gimignano with Dinner in a Boutique Winery?
A:The policies on sanitization are:

  • Hand sanitizer available to travelers and staff
  • Regularly sanitized high-traffic areas
  • Gear/equipment sanitized between use
  • Transportation vehicles regularly sanitized
See all safety measures taken by Small-Group Siena and San Gimignano with Dinner in a Boutique Winery.
What is the social distancing policy during Small-Group Siena and San Gimignano with Dinner in a Boutique Winery?
A:The policy on social distancing is:

  • Social distancing enforced throughout experience
See all safety measures taken by Small-Group Siena and San Gimignano with Dinner in a Boutique Winery.
What measures are being taken to ensure staff health & safety during Small-Group Siena and San Gimignano with Dinner in a Boutique Winery?
A:The policies on staff health & safety are:

  • Guides required to regularly wash hands
  • Regular temperature checks for staff
  • Paid stay-at-home policy for staff with symptoms
See all safety measures taken by Small-Group Siena and San Gimignano with Dinner in a Boutique Winery.

Traveler Photos

See More
See More

Traveler Tips

  • "A long tour to some very worthwhile hill top places." See review


77 Reviews

Reviews by Viator travelers

Showing 1-10 of 77 reviews
A truly valuable experience!
, 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.
, 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"
, 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.
, 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
, 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
, 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...
, 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!

Compare Similar Experiences

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


8 hours

Free Cancellation


Explore Similar Things to Do