Recently Viewed
Tuscany Highlights: Siena, San Gimignano, Chianti
4.6
232 Ratings
Firenze
Explore Siena and San Gimignano, savor Tuscan wines, and enjoy a sunset dinner in Chianti. Limited to 16 for a personalized experience.
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
- 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…
- 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 wine tasting
- Surprise tasting in Siena
- San Gimignano visit with free time
- Free Time in San Gimignano
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)
- 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…
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 Gimignano, the medieval town known for its towers, where you can leisurely stroll through its charming streets. As the sun sets, head to a scenic winery in the Chianti countryside for a traditional Tuscan dinner and wine tasting in a memorable setting.
Seeking the complete Tuscan adventure?
Opt for our Tuscany Grand Tour: a full-day excursion that also includes a visit to Pisa and its famous Leaning Tower, along with a Tuscan lunch. Follow in the footsteps of the Grand Tour travelers and immerse yourself in the art, history, and flavors of Tuscany from morning till night.
- The tour operates regardless of weather conditions
- Semiprivate Tuscany Grand Tour Option: Choose the Grand Tour upgrade for a full-day experience starting at 8:00 AM. Discover the highlights of Tuscany in one unforgettable journey: visit Siena with a guided walking tour and a surprise tasting, enjoy free time in the medieval town of San Gimignano, savor a traditional Tuscan lunch, then continue to Pisa to admire the stunning Piazza dei Miracoli and the iconic Leaning Tower (tower tickets not included). The experience includes round-trip transportation from Florence in a luxury Mercedes minivan with free Wi-Fi, an English-speaking driver/tour leader, and all the charm, history, and flavor of Tuscany in one complete itinerary.
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.6
(232 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Donwn9614xi
May 7, 2026
Great Italian Experience - Great experience. Lorenzo was fantastic guide.
Review provided by Tripadvisor
Tourist117963
May 7, 2026
A+ Siena & San Gimigano Tour & Dinner Tuscan Style & Wonery Boutique - Dotchia was a fresh of breathe air ! very informative allowing us to see the best at the area we stopped in. The secret views a taste of heaven . The winery was Superb, the dinner and again her knowledge and fun spirit made the trip its BEST experience possible !! Much gratitude 😍
Review provided by Tripadvisor
Debbieal3664pe
May 6, 2026
Awesome 👏 - We loved our tour and guide Lorenzo very much
Review provided by Tripadvisor
Mark
May 6, 2026
Beautiful cities and a fabulous dinner at a spectacular winery. - Beautiful cities and a fabulous dinner at a spectacular winery. The wine maker was a real blessing to be with, a lovely woman who is a sommelier and she shared her vast experience in tasting and making wine. The meal was marvelous and. Apples off the evening. Our tour guide, Haider, was an extremely entertaining and enthusiastic fellow that kept us going throughout. The local guide said n the city of Sienna was a very knowledgeable woman, Sara, who made the walk very enjoyable. Highly recommend this tour!
Review provided by Tripadvisor
794jeffu
May 6, 2026
A delightful adventure in Tuscany - Haider was warm, friendly and very entertaining! He was helpful and accommodating! Giovanna and her servers were delightful! The food was delicious and the wine was an absolute treat!
Review provided by Tripadvisor
Marku898
May 6, 2026
A fabulous day in Italy!!! - A truly special day of seeing 2 beautiful Italian towns, capped off by a fabulous dinner at a most splendid winery where the wine maker was a treasure. Our tour guide Haider was a real pleasure! The entire day is a treasured memory!
Review provided by Tripadvisor
Pamela
May 5, 2026
So much to do, so little time!! - Today was our second time touring with Haider from Towns of Italy this week! He is an incredible tour host, delightfully charming and entertaining, full of great information and stories of interest.
We enjoyed our day with him as he expertly drove us to Siena to meet up with Sara for our walking tour of her hometown city of Siena. She shared with pride and enthusiasm the history & highlights of her city during our hour-long visit (not nearly enough time l, by the way, as I could’ve spent a whole day there!) It is such a beautiful place full of interesting culture and traditions.
Then, Haider drove us to San Gimignano for another brief one-hour visit to an amazing ancient walled city on a hill overlooking so much of the Tuscan countryside. (Again, not nearly enough time here). He shared where to get the world’s best gelato (which it was!) and suggested we sit in the piazza and enjoy a glass of their famous Vernace white wine (which was delightful, as well).
Our final destination for an authentic Tuscan country meal with the most delightful hostess Giavanna was beyond extraordinary. We felt treated like family as she welcomed us into her home where her family has been for centuries and has direct ties to the Medici family. Her family ancestory is fascinating and there Chianti wines delicious!
Review provided by Tripadvisor
Cabrinhakitesurfer
May 4, 2026
Very nice tour - Very nice tour, I highly recommand it.
Review provided by Tripadvisor
G979rkkimf
May 4, 2026
Wine & Sienna Tour - This trip was fabulous. Our tour guide Tania was absolutely amazing. She was very engaging. Was very knowledgeable and knew the region well. I cannot say enough about her. Miguel in Sienna was good too. He took the time to explain everything you would want to know about Sienna.
Review provided by Tripadvisor
U3685ajjohnc
May 3, 2026
Great day trip from Florence - Great experience. The wine tasting and Tuscan dinner at the winery was outstanding and fun. Lots of walking up and down hills in Sienna.
Review provided by Tripadvisor
