Tuscany Day Trip: Chianti, Siena & San Gimignano

Embark on a gourmet adventure in the picturesque Tuscan countryside on a day trip from Florence. Explore the medieval town of Siena, savor a delicious lunch and wine tastings at a family-run farm in Chianti, and wander the enchanting streets of San Gimignano. Limited group size ensures a personalized experience.

Duration: 9 hours
Cancellation: 24 hours
Highlights
  • Tuscany - Your driver and guide will pick you up in a comfortable, air-conditioned transport in central Florence and drive you through the hills of Tuscany. You’ll pass the best panoramic viewpoint of Florence and pause for pictures.
  • Siena - Siena is one of the best-preserved examples of medieval Italian architecture in the world. Spared…
What's Included
  • Expertly guided walking tours of Siena and San Gimignano
  • Knowledgeable English-speaking guide
  • Professional driver designated for your safety
  • Gourmet lunch accompanied by a wine tasting in Chianti
  • Comfortable air-conditioned transportation
What's Not Included
  • Gratuities
  • Hotel Pick-Up/Drop-Off
Additional Information

Discover the highlights of Tuscany with this day trip from Florence to Chianti, Siena, and San Gimignano. Delight in a Chianti wine tasting at a local vineyard, wander through the medieval streets of Siena and San Gimignano, and indulge in a delectable Tuscan lunch featuring regional specialties, all included in your tour. Guided by a knowledgeable…

Location
Piazza della Repubblica
Please arrive 15 minutes prior to the start of your tour, your guide will be holding a green Walks sign. This tour meets by the Carousel in Piazza della Repubblica.
Cancellation Policy

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

Customer Ratings
4.8
(260 Ratings)
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G9299nuamyc
Oct 5, 2025
Lovely - Lovely tour with 2 great Italian cities. Wonderful lunch at winery with great food and wine. Guide was excellent and very knowledgeable.
Review provided by Tripadvisor
Fran
Sep 26, 2025
Superb day in Tuscany - Our family had a wonderful time on our trip to Sienna, Chianti and San Gimignano. Our tour guide, Jessica, was superb — fun, friendly and extremely knowledgeable. Our lunch was delicious with generous glasses of wine poured. I highly recommend this experience.
Review provided by Tripadvisor
O1845agchristianv
Sep 26, 2025
10/10 - This was a great tour! They accommodated my dietary restriction and it felt like time flew by in Siena and San Gimianno. Would recommend Jessica again!
Review provided by Tripadvisor
Robert_m
Sep 24, 2025
Perfect day in Tuscany - Perfect agenda Small groups Knowledgeable and congenial guide Great driver Wine tasting was wonderful, so much fun and great food
Review provided by Viator
Andra_b
Sep 23, 2025
Tuscan Treasures brought to life! - What a magical day! Antonio was the best guide…funny, knowledgeable and passionate. We were in a small group of 10, split across 2 luxury vans making it easy at every stop. The visit for lunch and wine pairings at the stunning Fattoria Il Colombaio was something very special, not to mention delicious. Marco and his family are winning at life. I HIGHLY RECOMMEND this tour and our guide.
Review provided by Viator
Jefe54
Sep 23, 2025
Great Introduction to Tuscany - Very comprehensive and interesting. The lunch and wine experience were delicious and educational. Selection of cities to visit helped helped get a good in””oicture of the history and culture of the region.
Review provided by Tripadvisor
Joann_v
Sep 22, 2025
Florence Day Trip through Tuscany - Great tour guide -very knowledgeable. The small group was more manageable. Siena and San Gimignano were beautiful and the winery was wonderful. Had the best time!!!
Review provided by Viator
Brady8
Sep 21, 2025
Excellent tour - This was an incredible tour. It was a nice taste of Tuscany for a day trip. Jessica our guide and Nicolas the driver were exceptional. Jessica was engaging and interesting and we learned a ton about the region and Italy. The stops in Siena and San Gigmiano were beautiful and the food and wine tasting delicious. Definitely take this tour
Review provided by Tripadvisor
Joseph_g
Sep 27, 2025
Nice tour - Tour guide Jessica and driver Gabriel were very nice Jessica was very informative Lunch was wonderful
Review provided by Viator
Romanaf607
Sep 18, 2025
All in all a very nice day - Nice and interesting excursion, great wine tasting, good guide, lots of information, a bottle of water in the car would have been desirable.
Review provided by Tripadvisor
From $221
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).