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Small Group Tour: Siena, San Gimignano & Chianti with Tuscan Lunch

4.9(481)9 hModerately active

From

$162per person

Book on GetYourGuide

Free cancellation up to 24 hours before

Overview

Duration: 9 h
Pace: Moderately active

Good for

Couples
First-time visitors
Food lovers
Groups of friends

Discover Tuscany's charm on a guided small-group tour. Explore medieval Siena with a guided walk, wander through San Gimignano's streets, and savor a typical Tuscan lunch with local wines and olive oil at a winery.

Highlights

Admire the Tuscan countryside
Typical Tuscan Lunch
Guided Exploration

What's included

Small group day trip to Siena and San Gimignano from Florence
Professional and informative English speaking guide + driver
Roundtrip transportation by fully equipped minibus or minivan
Guided walking tour of Siena highlights + free time in Siena
Light lunch at a Tuscan winery, paired with their excellent red wines
Free time in San Gimignano for self exploration
Siena Cathedral entry ticket and guided tour (unless add-on selected during checkout) - NOT AVAILABLE ON SUNDAY
Hotel pickup and drop-off
Tips

Before you go

What to bring

Passport or ID card
Weather-appropriate clothing

Good to know

Vegetarian menu can be catered for, upon request at the time of booking
Sample menu: assorted cold cuts, cured ham, salami, cheeses, bruschetta, pasta or soup, and dessert, accompanied by the winery's own wines, olive oil, etc.
The tour operates rain or shine
The Siena Cathedral is not accessible on Sundays or during religious celebrations
For cruise ship passengers only: if your ship docks at Livorno or La Spezia Port, be advised that the driving time to the meeting point in Florence is approx. 2 hours. Before booking, be sure your ship schedule works with our departure times, and you have your own transportation arranged from the port to Florence and back.

From$162per person

GetYourGuide

BookBook on GetYourGuide

Learn more
About the team
A snapshot of who will guide your experience
Completed activities
1,100+
Years on GetYourGuide
13+
1,100+ completed activities
13+ years on GetYourGuide
activities in English
Guide reviews
Georgina – Australia
G
October 3, 2025 - Verified booking
The tour was great! Lorenzo our guide was very knowledgeable & shared interesting information about Siena, San Gimignano & the surrounding areas. With a great sense of humour, he made everyone feel welcomed & well looked after. Props too, to Alex our bus driver, who navigated the tight roads with ease & assisted with taking our photos. The tour was relaxed, it didn’t feel rushed yet we saw & heard about many details. I especially enjoyed the information about the Siena horse race & the rivalry between families. Paying extra for a smaller group is well worth it for a more intimate experience. I would definitely recommend the tour.
Couple
Yelena – Australia
Y
October 5, 2025 - Verified booking
We had a wonderful day trip to Siena and San Gimignano! Our guide Lorenzo was fantastic — knowledgeable, friendly, and passionate about the history and culture of Tuscany. He brought the medieval towns to life with fascinating stories and made sure everyone in the group was comfortable and engaged throughout the day. Our driver Sergio was excellent too — very professional, punctual, and smooth on the winding Tuscan roads. The itinerary was perfectly planned with enough time to explore, take photos, and enjoy a relaxed lunch. It was the perfect way to experience the beauty of Siena and San Gimignano without any stress. Highly recommend this tour, especially with Lorenzo and Sergio — they made the day truly memorable!
Sarah – Canada
S
October 22, 2025 - Verified booking
Siena and San Gimignano were beautiful. Lorenzo, our guide, was excellent. He was a great storyteller and told us ahead of time ( on the bus) what to expect, where to meet etc. And then showed us in-person and pointed out important details like washroooms and scenic viewpoints. I have been on many tours and Lorenzo was a pro and made the day.
Response from Provider
Hello Sarah! Thank you for your wonderful review! We’re thrilled Lorenzo made your day in Siena and San Gimignano so memorable with his storytelling, guidance, and attention to detail. It’s great to hear he made the tour seamless and enjoyable! We hope you take back beautiful memories of your day!
November 19, 2025
Solo traveler
Matthew – United States
M
November 7, 2025 - Verified booking
Great trip overall perfect balance of guide and free time. Both the driver and guide in Siena were amazing
Hello Matthew! Thank you for your wonderful review! We’re thrilled you enjoyed the perfect balance of guided time and free time. It’s fantastic to hear that both the driver and guide in Siena made your trip memorable. We’d love to welcome you back for another great experience in the future!
November 14, 2025
Laurie – United States
L
November 18, 2025 - Verified booking
Great small group tour to Siena, lunch at Mensanello winery (Neri a great host) and San Gimignano. Francesco was an excellent guide for our drive in beautiful Tuscany.
Hello Laurie! Thank you for the wonderful review! We're so glad you enjoyed the small-group experience to Siena and San Gimignano. Lunch at Mensanello is always special, and Neri will be happy to hear your kind words. Francesco will be thrilled to know he helped make your day in Tuscany memorable. We appreciate you joining us and taking the time to rate/ review us as well!
Susan – United States
November 25, 2025 - Verified booking
Excellent! Just the right mix of history, food and wine and free time to enjoy the beautiful cities. Truly amazing tour!
Hello Susan! Thank you for the fantastic review! We're so glad the tour struck the perfect balance of history, food, wine, and free time for you. It’s wonderful to hear you enjoyed the beautiful cities and had an amazing experience. We hope to welcome you on another tour in the future!
November 25, 2025
Friend group
Stelian – Romania
November 9, 2025 - Verified booking
A beautiful experience, acompanied by an excelent guide - Suzanna, well documented, giving us a lot of information, and a good driver - GianLuca. Siena and its Chatedral are amazing, and local guide - Carlo, very proud of his town, presenting us a lot of stories about this wonderful site. San Gimignano is a live story!
Hello Guteanu! Thank you so much for sharing your experience! We’re thrilled to hear that Suzanna’s guidance and GianLuca’s driving made your day seamless and enjoyable. It’s wonderful that you appreciated Siena, its cathedral, and Carlo’s passionate storytelling, as well as the charm of San Gimignano. We’re delighted the tour left such a lasting impression!
November 11, 2025
Travelers say the guides are <strong>knowledgeable, funny</strong> and <strong>personable.</strong>
Cancel up to 24 hours in advance for a full refund

Restrictions & safety

People with mobility impairments
Wheelchair users