Tuscany Highlights: Siena, San Gimignano, Chianti

Explore Siena and San Gimignano, savor Tuscan wines, and enjoy a sunset dinner in Chianti. Limited to 16 for a personalized experience.

Duration: 12 hours
Cancellation: 24 hours
Highlights
  • Florence - Designated meeting location in the towns of Italy
  • Siena - Arrival in Siena for an informative guided tour
  • Historic Centre of San Gimignano - Leisure time in San Gimignano, a UNESCO World Heritage Site
  • Diadema Wine & Evo - Enjoy a gourmet dinner at a boutique winery in Chianti
  • Florence - Return to Florence, concluding the tour at the original meeting location
What's Included
  • Free WiFi on board
  • English speaking driver/tour leader
  • Typical Tuscan dinner or Lunch for the Tuscany Grand Tour Option
  • Transportation IN/OUT Florence by luxury Mercedes Minibus or Minivan
  • Guided walking tour of Siena
  • Tuscany Grand Tour Option: Visit to Pisa and Miracle Square (Leaning Tower entrance not included)
  • Visit of a winery with…
What's Not Included
  • Gratuities
  • Hotel pickup and drop-off
  • We are sorry to inform you that pets are not permitted on our tours
  • Tuscany Grand Tour Option: Entrance ticket to the Tower of Pisa (purchase on-site if time allows)
Additional Information

Experience the highlights of Tuscany in a single enchanting afternoon! Begin your journey in Florence and travel in a luxurious minivan through the picturesque Chianti hills. Enjoy a guided walking tour of Siena, where you can explore its Contrade, Piazza del Campo, and magnificent Gothic architecture. Savor local delicacies before proceeding to San…

Location
Via dei Vagellai, 22
Via dei Vagellai
Via dei Vagellai 22R, at the corner of Piazza Mentana (across from the Arno River)
Cancellation Policy

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

Customer Ratings
4.6
(211 Ratings)
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1 star
Yurif929
Dec 30, 2025
Great experience in picturesque Tuscany towns - The tour was great and went above all my expectations. The leg in Siena was super interesting and a local guide showed us many interesting places and the history behind them. St Gimignano is a picturesque little town and was worth the stop. Finally the dinner in the winery was amazing both for the food and wines The staff was super friendly and made sure everyone was comfortable and entertained during all the tour.
Review provided by Tripadvisor
Stevenew3896vc
Dec 29, 2025
Amazing Experience - This was a phenomenal trip! Our favorite part was the winery visit at the end. Would highly recommend! Don't be afraid of the 8.5 hour trip length. It is worth every minute.
Review provided by Tripadvisor
Annatamm
Dec 24, 2025
Christmas Tour or Florence and Siena! - Francesca and Jacobo were so fantastic!!! Would recommend to anyone to take a tour with them!!!! Good people!! Wine tasting w/: fantastic and walking tours were amazing!!
Review provided by Tripadvisor
Javieraz1962kw
Dec 19, 2025
We had a spectacular day with Romana touring Siena, San Gimignano, and ending with an unforgettable home-cooked meal at - We had a spectacular day with Romana touring Siena, San Gimignano, and ending with an unforgettable home-cooked meal at a winery in Chianti. Everything was beautifully planned from the wine tasting to the incredible food—but what truly made the experience special was Romana herself. She was warm, knowledgeable, and made the entire day feel personal and relaxed. It was an authentic Tuscan experience we’ll always remember. Highly recommended
Review provided by Tripadvisor
Excursion612312
Nov 28, 2025
Good time - Great tour guide Lorenzo. Enjoyed both cities and the winery. All was planned well we had a good time. We went in November
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Maryann
Nov 12, 2025
Terrific tour - Grace was informative and very personable. She spoke of the history of the region as we dove through each region. She elicited questions in a friendly manner wanting to know more about our group to enrich her presentation
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757kemberlys
Nov 7, 2025
Amazing!!! - Excellent tour! Winery was awesome! Winery owner is the sweetest! This was such a great experience! I learned so much about the making of the wine and what to pair each wine with. AND… the dinner was AMAZING!
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494karthika
Nov 7, 2025
Tour with Dinner - Excellent guided tour matched with eccellente dinner and Wine testing at winery. This was in Seina and San Giammamo. Personable and detail oriented
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Roam58802392996
Oct 29, 2025
Afternoon experience - Was great! Thanks claudia! Afternoon tour end of october was a bit late but it was still great!! Especially the wine farm at the end!!
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Nicolels2508ve
Dec 16, 2025
Tuscany outing experience - Claudia greeted us right on time at the meeting point and gave us all sorts of great knowledge and facts as we drive to Siena. After a little free time we continued to San Gimignano which was also wonderful but the best part of the experience was the winery and dinner. Giovanna (the owner) greeted us and ended up staying for wine and sharing stories. She was amazing!!
Review provided by Tripadvisor
From $168
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).