Best of Tuscany: Siena, San Gimignano & Winery Tour with Lunch

Overview

Available languages

English

9 hours

Mobile ticket

Looking for an effortless way to discover Tuscany from Florence? Craving a visit to a renowned Chianti winery and a glimpse of the breath-taking vistas in San Gimignano? Look no further, for you have found the ideal tour!

With round-trip transportation and a tour leader to accompany you on your Tuscan adventure, all you have to do is sit back, enjoy local wines, and let the beauty of this region overwhelm you.

First stop, on the day, will be Historic Siena - known for its famous Palio races. Where you'll enjoy some free time after visiting its main square with our trip leader.

Next, onwards to a traditional winery for a wine tasting and delicious local lunch! After learning about the wine making process a wine tasting and delicious lunch, we'll proceed to the final stop for the day.

San Gimignano, also known as the Medieval Manhattan s is a must-visit when in Tuscany. Enjoy leisure time in the fairytale like city before being whisked back to Florence.

Additional Info

Public transportation options are available nearby

Specialized infant seats are available

Not recommended for pregnant travelers

Travelers should have at least a moderate level of physical fitness

Due to traffic regulations, all children must be seated. Car seats are available upon request which must be made at least 72 hours in advance.

If you have any food allergies or intolerances, please contact us immediately to let us know. We work with our local vendors to plan menus ahead of time so having this information before your tour is important. Please note that there are some occasions where certain allergies cannot be accommodated.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

What‘s Included

Local and fun, English-speaking trip leader

Enjoy a wine tasting, sampling 6 of the region’s finest wines.

Free time in the picturesque medieval town of San Gimignano

Guided tour of the cellar and vineyards at a family-run Chianti winery.

Explore charming Siena with free time to visit the Cathedral (ticket excluded)

Round-trip Transportation from Florence in an Airconditioned Vehicle

Savor a traditional 3-course Tuscan lunch featuring local specialties

Hotel pick up / drop off

Entry to the Siena Cathedral

Entrance fees to ticketed places in San Gimignano

Gratuities (optional)

What To Expect

Kick off your Tuscan adventure with a warm welcome from your tour leader in Florence. Your journey begins with a scenic, 1.5-hour drive through Tuscany’s hills and vineyards in our comfortable, air-conditioned transport, setting the tone for an unforgettable day. First stop: the stunning city of Siena!"

Options

Best of Tuscany: Siena, San Gimignano & Winery Tour with Lunch

Reviews

4.70

71 reviews

Total reviews and rating from Viator & Tripadvisor

Lori the best Tour Guide!!
Maps01926096549,
Oct 31, 2025
- Review from Tripadvisor
5.00
Lori was amazing tour guide. Very sensitive to the needs of my friend who had problem keeping pace with other tourist. Also she sent my kindle to US ( California) which I forgot in my hotel room. She took trouble to DHL to California taking out time from her busy schedule! I recommend every tourist to take her as a tour guide to Sienna,wine tour and San Gimmignana!! Well done Lori! Love from Meetu and Gurmeet and Geve!!
Florence wine tour
Susan D,
Oct 20, 2025
- Review from Viator
1.00
The pick up location was not what was confirmed on my app and therefore we missed our tour. Please update the location on the app for your clients as this was very disappointing. We could not go as we were leaving Florence the day which was very frustrating.
Great day in Tuscany
Carol K,
Oct 10, 2025
- Review from Viator
5.00
The tour guide and his driver were great. Stops in beautiful Siena and San Gimignano were fabulous. Although the winery experience was wonderful, was a bit put off by the focus on selling their products (balsamic vinegar, olive oil and wine).
See the most for your money
Leanne C,
Oct 7, 2025
- Review from Viator
5.00
This tour really made the wine tasting fun . It was very informative and was a great value that included a delicious lunch which enabled us to meet people from other countries . Seeing the extra two towns was wonderful but made it quite rushed.
Lovely Tuscany Wine Tour
Debra B,
Oct 5, 2025
- Review from Viator
5.00
Our Wine Tour was amazing Our guide. Frederika, was knowledgeable, kind and attentive . She was able to deal with my cane-walking husband without affecting other travelers. The driver (sorry... I can't remember his name) was likable, but more importantly capable, during a full day of driving a d stops. The winery family information was extraordinary. We would highly recommend this excursion!
Excellent tour
Cindy T,
Oct 3, 2025
- Review from Viator
5.00
Our host, Ana, was wonderful. She was so friendly, answerd everyone s questions and did a great job maki g sure we all got on the bus at each stop. The driver was on time and did a great job getting us safely to and from our stops. Lunch at the winery was so good. I wish I would have choosen a longer tour as 9 hours went by quickly.
Great wine! Food and fun!
Shelly W,
Sep 22, 2025
- Review from Viator
5.00
Fun, great food, wine selection and guides. I was very impressed with how seamless the day was. I highly recommend spending the day on this tour.
A nice day if you want to briefly see a bit of everything
Matthew C,
Sep 22, 2025
- Review from Viator
4.00
This tour was fun, interesting, and worth it. I give it a 4 or 4.5 instead of full marks only because I think they should give more time in either Siena or San Gimignano and cut the other. On the one hand, it is super cool to see both, but on the other they're both pretty rushed. The tour guide, Anna, was amazing!
Our tourguide Frederica...
Hester N,
Sep 21, 2025
- Review from Viator
4.00
Our tourguide Frederica was just perfect and so helpfull - really the best. The bus was very comfortable. We enjoy enough time in the 2 little towns. Was fun picking grapes. Food and wine was good. The salesman at the winery was just to much in trying to sell his wines. The feeling I am going home with ... it was not about the comfort of the guests - only about how many wine they can sell.
A Tuscan Day Dream with Wine and Wonders
Rajeev N,
Sep 16, 2025
- Review from Viator
5.00
This tour perfectly blends stunning Siena and San Gimignano with a relaxing Chianti wine tasting. Our guide was knowledgeable and friendly, and the lunch at the vineyard was delicious. A fantastic way to soak in Tuscany’s highlights in one day!