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
(243 Ratings)
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A3017lsnicoleb
Jul 22, 2025
- This Tuscany day trip was one of the highlights on my holiday to Italy. The tour guide Antonio was very knowledgeable about the history of Siena and San Gimignano. He guided us through the towns, and cultivated in us an appreciation of what we were seeing. Antonio was the perfect guide! Exploring Siena and San Gimignano was an amazing experience as well as the visit to the winery. I got a taste of Tuscany, and it left me wanting more.
Review provided by Tripadvisor
Leisa
Jun 30, 2025
Great way to see Tuscany - Antonio was a very informative guide who shared some really interesting information about Florence and the history with Sienna. The tour was well planned to avoid the busiest areas at peak times. Sienna is absolutely beautiful and would be a great place to stay if you had time. The winery lunch was very enjoyable with a delightful host. Definitely recommend this small group option.
Review provided by Tripadvisor
Ruthellen_l
Jun 9, 2025
Great tour - Our guide, Elena, was warm, friendly, and engaging. I loved that we went first to San Gimignano before it got too crowded. Lunch at Fattoria Il Colombaio was wonderful. Be sure to buy a ticket to go inside the Duomo; it's magnificent! The vans were like new and very comfortable.
Review provided by Viator
Wander797531
Jun 2, 2025
Awesome - Fantastic tour, extremely knowledgable guide. Comfortable vans. Jessica was very historical and each stop was like travelling thru time.
Review provided by Tripadvisor
Sibby_d
May 28, 2025
Great Tour - Elena was our guide and she was wonderful!! She was very knowledgeable on our tour of Siena and San Gimignano. The winery was lovely and the food delicious. Sit up front in the van if you are prone to car sickness because the ride to and from Florence is a little frantic. But overall, I would highly recommend this tour.
Review provided by Viator
K4157wqcelestec
May 26, 2025
Just what we needed! - Jessica is very knowledgeable and kind. The tour was well paced, the towns were breathtaking and we left the food and wine tasting part of the tour very full - very satisfied!
Review provided by Tripadvisor
Louis_r
May 20, 2025
Memorable day! - Exceptional experience throughout the whole day. Personal guide was enthusiastic, knowledgeable and kind. My family had an amazing time. All sites chosen were incredibly memorable. Would highly recommend.
Review provided by Viator
James_m
May 10, 2025
Wine & Dine - Our tour guide was very informative and good group of people. An added bonus was a stop at the Piazzale Michelangelo before heading out. The tour does not include entry to the Duomo in Siena. If you want to see the inside, purchase tickets ahead of time as the line was long & you'd spend your free time on line. The wine tasing and lunch was very good and a nice break from walking.
Review provided by Viator
Nicpac99
May 3, 2025
Beautiful Tuscany - One of my favorite days of the trip... seeing the medieval city of San Gimignano with such history and beauty, then lunch at a vineyard. We were hosted by the incredibly warm and lovely family that owns the vineyard, had an amazing lunch and wine pairing - perfect afternoon! Then on to Siena to see more modern Tuscan life. Wonderful day, and Tommaso Rampi was a fantastic guide and driver!
Review provided by Tripadvisor
Annmx3072ga
May 2, 2025
Siena, Chianti, San Giorgamano - Jessica was an amazed ng tour guide. Warm and knowledgeable. Our tour went to Sienna, a winery in Chianti, and San Gigignano. We had a great balance of guided tour and time on our own to explore. I highly recommend Jessica!
Review provided by Tripadvisor
From $222
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).