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Tuscany Wine Tasting: Siena, San Gimignano, & Monteriggioni Escorted Tour with Tuscan Lunch
4.5
171 Ratings
Firenze
Experience the best of Tuscany on this escorted tour. Visit Siena, San Gimignano, and Monteriggioni, enjoy a Tuscan lunch and wine tasting, and explore at your own pace.
Experience the best of Tuscany on this escorted tour. Visit Siena, San Gimignano, and Monteriggioni, enjoy a Tuscan lunch and wine tasting, and explore at your own pace.
Duration:
11 hours
Cancellation:
24 hours
Highlights
- Historic Centre of San Gimignano - Discover a beautifully preserved walled hilltown renowned for its impressive medieval towers and fresco-adorned churches. Meander through the UNESCO-listed historic center at your leisure, exploring artisan shops and tranquil lanes. Relish panoramic views over the Val d’Elsa and take time for gelato or souvenirs….
- Historic Centre of San Gimignano - Discover a beautifully preserved walled hilltown renowned for its impressive medieval towers and fresco-adorned churches. Meander through the UNESCO-listed historic center at your leisure, exploring artisan shops and tranquil lanes. Relish panoramic views over the Val d’Elsa and take time for gelato or souvenirs.
- Monteriggioni - Enter a charming fortress village surrounded by well-preserved 13th-century walls. Explore the quaint piazza and gates, absorbing its genuine medieval charm. A quick, easy visit with excellent photo opportunities from the ramparts.
(*) From November to March, the itinerary excludes the stop at Monteriggioni and the return to Florence is approximately 30 minutes earlier.
- Chianti Road - Travel along one of Tuscany’s most picturesque roads, passing vineyards, olive groves, and stone farmhouses. Relax at a cozy winery for a guided tasting of three Chianti wines paired with a locally-sourced, three-course lunch. Conclude with traditional cantucci and vin santo.
- Siena - Enjoy ample free time to experience Siena’s Gothic essence—narrow lanes, noble palaces, and vibrant enotecas. Explore artisan boutiques, savor local delicacies, and capture the city’s warm, terracotta tones. Perfect for independent exploration and leisurely photos.
- Duomo di Siena - Take a moment for an exterior and brief interior view of Siena’s striking striped-marble cathedral. Appreciate its elaborate façade, sculptures, and masterpieces that reflect the city’s artistic prowess. A quick yet memorable highlight.
- Piazza del Campo - Enter one of Italy’s most stunning squares, famous for the Palio horse race. Pause to sit at a café, admire the shell-shaped slope, and view the Torre del Mangia and Palazzo Pubblico. An ideal conclusion for people-watching and photography.
What's Included
- Caf Tour staff assistance at the meeting point for smooth check-in
- Licensed English-speaking tour escort throughout the day
- Chianti winery experience: guided visit of cellars and vineyards & 3-course traditional Tuscan lunch
- Wine tasting: three different Chianti wines plus classic vin santo
- Tasting of three different Chianti Wines, extra virgin…
- Caf Tour staff assistance at the meeting point for smooth check-in
- Licensed English-speaking tour escort throughout the day
- Chianti winery experience: guided visit of cellars and vineyards & 3-course traditional Tuscan lunch
- Wine tasting: three different Chianti wines plus classic vin santo
- Tasting of three different Chianti Wines, extra virgin olive oil, balsamic vinegar & vin santo
- Round-trip transport by air-conditioned coach
What's Not Included
- Guided Service in Siena
- Cathedral admission in Siena
- Guided Service in Siena
- Cathedral admission in Siena
Additional Information
Discover the beauty of Tuscany in a day from Florence with an 11-hour coach tour visiting San Gimignano, Monteriggioni, Chianti, and Siena. Journey through medieval towers, charming walled villages, and picturesque vineyards. Enjoy the freedom to explore the UNESCO-listed historic center of San Gimignano at your leisure and step into Monteriggioni’s…
Discover the beauty of Tuscany in a day from Florence with an 11-hour coach tour visiting San Gimignano, Monteriggioni, Chianti, and Siena. Journey through medieval towers, charming walled villages, and picturesque vineyards. Enjoy the freedom to explore the UNESCO-listed historic center of San Gimignano at your leisure and step into Monteriggioni’s impeccably preserved fortress. Travel along the scenic Chiantigiana road to a welcoming winery for a guided tasting of three Chianti wines and a locally-sourced, three-course lunch, concluding with cantucci and vin santo. Spend free time in Siena wandering Gothic streets, exploring artisan shops, and relaxing in vibrant enotecas. Make brief visits to the striped Duomo and the shell-shaped Piazza del Campo, famous for the Palio. Perfect for those who appreciate art, wine, and stunning views in a seamless day—round-trip transport and a tour leader are included.
(*) From November to March, the itinerary excludes the Monteriggioni stop, and the return to Florence is approximately 30 minutes earlier.
- For small groups, up to 8 pax, the Tour escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.
- Comfortable walking shoes are recommended
- Please note that the order of the visits may change
- It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the excursion, nor to have a refund or reschedule the tour.
- Please be advised that it is required to bring your original ID with you during the tour
- Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
Location
Piazzale Montelungo
An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.
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
4.5
(171 Ratings)
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Bonnie_s
Nov 13, 2025
A day in Chianti, Siena & San Gimigniano - The tour was very well organized and managed by Sandro who led the group through the history of this part of the Chianti region. He was very knowledgeable & pleasant.
The lunch was delicious & accompanied by tasting of 2 types of Chianti wine & a vin Santo.
Lucia, the guide to the Siena cathedral, was excellent & very thorough
Review provided by Viator
James_m
Oct 11, 2025
Adventure in Tuscany - Just a nice time. Constantino ( I believe that was his name) was informative, passionate and funny. Much Enjoyed lunch and wine in Tuscany winery. The only (small) issue I had was the tour had English and Spanish translation. You should separate the 2 audiences (thought Constantino handled it well!)
Review provided by Viator
Stefanny
Oct 7, 2025
Fascinated with the tour - Loved it❤️❤️❤️... I don't remember the name of the two guides but they were very friendly and friendly... They were super punctual and tidy with the itinerary... And the places were spectacular... Dondoli Gelateria ice cream is deliciousoo😋
Review provided by Tripadvisor
Nancy_w
Sep 25, 2025
A day in Tuscany - Great experience and easy way to get out of Florence for the day to see other areas of Tuscany. It was well organized even for a large group. Lunch was great with the wine tasting and seeing medieval villages was just amazing.
Review provided by Viator
Reviewsbykate
Sep 6, 2025
A Perfect Day in Tuscany - We had a great experience on this tour, thanks to our guide Jakopo and driver Raul. Jakopo was polite and very informative, sharing lots of interesting facts about Tuscany throughout the day. He also gave clear instructions about meeting points and times, which helped everything run smoothly. Raul, our driver, was equally professional and ensured we arrived safely at each destination.
Our first stop was Monteriggioni, a charming little town where we had about 30 minutes—just enough time to grab a coffee and take in the atmosphere. We then spent around three hours in Siena, which felt like plenty of time to explore the historic streets, enjoy a delicious lunch at a local restaurant, and pick up a souvenir.
After Siena, we stopped at Poggio ai Laghi for a wine tasting experience. We sampled four different wines, two types of balsamic vinegar, and a selection of bread and cold cuts—definitely a highlight of the day.
Our final stop was San Gimignano, where we had 1.5 hours. While we enjoyed exploring this beautiful hilltop town, we would have loved a bit more time there, as it felt slightly rushed compared to the earlier stops.
Overall, it was a well-organized tour with a good mix of cultural exploration, food, and relaxation. Highly recommended for anyone wanting to experience the best of Tuscany in a day.
Review provided by Tripadvisor
Nelson_a
Aug 30, 2025
Good time - The tour was good. We got to see a few different towns and got some lunch and wine as well.
I loved Siena, skip the walking tour and see the cathedral and main square yourself. Definitely don’t have enough time to enjoy it all.
Overall, it was a great tour and Marta was amazing!!!
Review provided by Viator
Sabine_b
Aug 19, 2025
Beautiful first impressions of the cities - The wine tasting was a bit long and there was no alternative, otherwise everything was very nice, especially Siena
Review provided by Viator
Angela_h
Aug 12, 2025
A wonderful trip to Tuscany - We enjoyed the trip very much. We left Florence on time and returned as scheduled. The time in each city was more than enough to walk and see the main attractions. The visit at the winery was very pleasant, first we tasted two types of spumant wines and learned more about the winery, then we had a three course meal paired with three different Chianti wines. Our guide Marta was very nice, friendly and shared a lot of information with us about the trip and also gave us very clear information about meeting points, attractions we should see and places to shop or have a gelato. The driver Giovanni was very nice, we had a smooth drive. They both deserve a five star. All in all we spent a very nice day and we were pleased with the CAF Tour and Travel tour operator.
Review provided by Viator
Ana_r
Jul 31, 2025
Great tour - Sandro went above and beyond. He loves his work and it shows. The information provided was perfect. The tour itself was great definitely worthwhile. Sandro really went out of his way to help me since I wasn’t able to walk alot
Review provided by Viator
Stephanie_d
Oct 13, 2025
Good tour but room for improvement: Great destinations, great guide, poor lunch, too many people. - Overall: Great destinations, great guide, poor lunch, too many people.
Great tour guide, very friendly. Fantastic locations. Too many people for it to be personal at all. It’s a full double-decker Coach bus completely filled with people. If you get stuck sitting in the back of the bus, you have to wait for everyone else to get off first which wastes time at each location. Felt like a hierarchy of seating arrangement.
Winery lunch was mediocre. Winery was not spectacular. They turn over hundreds of people a day and the food was basic. Lots of yelling to explain each wine.
Review provided by Viator
