San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Description
Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore the UNESCO historic center of San Gimignano at your own pace; step inside Monteriggioni’s perfectly preserved fortress. Follow the scenic Chiantigiana road to a cozy winery for a guided tasting of 3 Chianti wines and a zero-mile, 3-course lunch, finishing with cantucci & vin santo. Enjoy free time in Siena to wander Gothic lanes, browse artisan shops, and relax in lively enotecas. Quick stops at the striped Duomo and shell-shaped Piazza del Campo, home of the Palio. Ideal for travelers seeking art, wine, and views in one effortless day—round-trip transport and tour leader included. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
Tour Options
Itinerary
Explore a perfectly preserved walled hilltown famed for its soaring medieval towers and fresco-filled churches. Stroll the UNESCO-listed historic center at your own pace, browsing artisan shops and quiet lanes. Enjoy panoramic viewpoints over the Val d’Elsa and time for gelato or souvenirs.
Step inside a storybook fortress village encircled by intact 13th-century walls. Wander the tiny piazza and gates, soaking up its authentic medieval atmosphere. Quick, easy visit with great photo spots from the ramparts. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
Cruise one of Tuscany’s most scenic roads, rolling past vineyards, olive groves, and stone farmhouses. Settle into a cozy winery for a guided tasting of three Chianti wines paired with a zero-mile, three-course lunch. Finish sweetly with traditional cantucci and vin santo.
Enjoy generous free time to feel Siena’s Gothic soul—narrow lanes, noble palaces, and lively enotecas. Browse artisan boutiques, sample local specialties, and capture the city’s warm, terracotta hues. Ideal for independent discovery and relaxed photos.
Pause for an exterior and brief interior look at Siena’s striking striped-marble cathedral. Admire its ornate façade, sculptures, and masterworks that hint at the city’s artistic power. A swift but unforgettable highlight.
Descend into one of Italy’s most beautiful squares, famed for the Palio horse race. Take a moment to sit at a café, admire the shell-shaped slope, and view the Torre del Mangia and Palazzo Pubblico. A perfect finale for people-watching and photos.
Highlights
What's included
Traveller Ratings
Important Information
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Travelers should have at least a moderate level of physical fitness
- 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.
- Vegetarian and gluten-intolerant options are available at the wineries; however, cross- contamination cannot be fully excluded.
Reviews(176)
I had a good time. The tour was efficient, with minimal waiting time and a good balance of time allocated to each segment. Thank goodness for the air-conditioned bus ride. The driver Gabriel and guide Fabi were excellent. Fabi was knowledgeable and articulate in both English and Spanish, which made the trip enjoyable.
This is a great tour. We went to the medieval museum and a torture museum in San Gimignano, both were free. Look up each town ahead of time or while on the bus to see what you want to do. Lunch was a great time.
Good Morning from Caf Tour & Travel, Dear Angela, Thank you so much for sharing your experience with us. We are delighted to hear you enjoyed discovering the medieval charm of San Gimignano and appreciated the variety of experiences available throughout the day, together with the relaxing lunch stop along the journey. Tuscany offers such an incredible combination of history, culture and authentic flavors, and we are happy you had the chance to experience so much in one unforgettable day. We hope to welcome you again soon for more beautiful Italian adventures. Arrivederci and see you soon, Caf Tour & Travel Team
Excellent way to see and experience multiple Tuscany cities in one day. Winery was nice, but simple. Somewhat long day and requires uphill walking.
Good morning from CAF Tour & Travel! Dear Charlene, Thank you very much for your kind review! We are happy to hear that you enjoyed the Tuscany experience and appreciated visiting multiple cities in one day. We also thank you for your note regarding the walking and winery experience, which we will take into consideration. We hope to welcome you again soon! Kind regards, CAF Tour & Travel Team
This was wan excellent day tour and value for money. The check-in process was seamless. The guide (fabi) and driver (Giovanni) made the experience so enjoyable. The three towns are a must see. The lunch and wine tasting was amazing and very informative.
Good Morning from Caf Tour & Travel, Dear John, Thank you for your fantastic review! We’re so happy to hear that you enjoyed every aspect of your tour, from the seamless check-in to the beautiful towns, lunch, and wine tasting experience. A special thank you for mentioning Fabi and Giovanni, we’ll be delighted to share your kind words with them. Hope to see you again for another amazing Italian journey! Kind regards, Caf Tour & Travel
I am writing this to warn other travelers: **Do NOT trust your vacation or your money with Caf Tour & Travel.** My family and I arrived promptly at 8:00 AM for our tour to Siena and San Gimignano, only to be left in the lurch. We were not alone; several other passengers were also left stranded at the meeting point with zero explanation. The lack of professionalism that followed was even worse than the logistical failure: * **Blatant Avoidance:** They completely ignored our urgent text messages. * **Hung Up On Me:** When I finally got through to them on the phone to resolve the situation, the representative disconnected the call on me** the moment I explained we had been left behind. It is one thing to have a scheduling error; it is quite another to show such cowardice and a total lack of accountability. They took our money, ignored our presence, and then literally hung up on us when confronted. We have been forced to scramble and navigate public transportation ourselves just to save our day This agency is unreliable, unprofessional, and clearly has no regard for the families who book with them. Save yourself the stress and book with anyone else in Florence.
Dear Suzanne, We’re very sorry to read your review, but we must clarify what actually happened. According to our records, you contacted us on WhatsApp at 8:06 AM stating that you were at the meeting point. However, both on your voucher and on all our official platforms, it is clearly specified that the meeting time is 15 minutes before departure, which in your case was 8:00 AM. This means that arrival after that time is considered late. It is also clearly stated in the booking conditions that in case of late arrival, it is not possible to provide a refund, as the tour departs on schedule out of respect for all other participants. Regarding communication, our office is fully operational from 7:00 AM, and we actively respond to landline calls, emergency numbers, and WhatsApp messages. In fact, as you mentioned, you did receive a reply shortly after your message. We always do our best to assist guests in real time, but unfortunately we cannot delay departures or make exceptions that would impact the entire group. We understand that missing a tour is frustrating, especially while traveling, but in this case all the relevant information was clearly communicated in advance and our team remained available throughout. Warm regards
Tour company was very solid. Kept things moving on time. Bus was comfortable, but not a lot of legroom for a person who is 6'1". The winery was WEAK! Food was decent, but the wine was not particularly good. Also was direct to consumer scheme, so pretty hard sell to the point we're they offered to set up a wine tasting in our home in the States (think Tupperware party). Pretty off putting. Also, facility was industrial, not your picture of a wine estate in Tuscany.
Dear Daniel, Thank you for sharing your detailed feedback. We’re glad to hear that the tour ran smoothly, the bus was comfortable, and the overall experience of exploring San Gimignano, Siena, and Monteriggioni was enjoyable. We appreciate your comments regarding the winery visit and understand that it did not meet your expectations. Your observations are valuable and will help us in selecting experiences that better match our guests’ expectations in the future. Thank you again for taking the time to share your experience, and we hope to welcome you back to Tuscany for more memorable moments. Warm regards from Tuscany, CAF Tour & Travel Team
Martha was the host, she was great! She always had lots of info for each place we visited. Such nice towns we visited. Love the area! Would recommend the tour.
Good Morning from Caf Tour & Travel, Dear Brenda, Thank you so much for your kind review! We’re thrilled that Marta’s warmth and wealth of information made your tour so enjoyable. It’s wonderful to hear that you loved the charming towns you visited, Tuscany truly has a way of capturing hearts with its beauty and history. We would be delighted to welcome you back soon to discover even more of the region’s treasures and unforgettable experiences. Warm regards from Tuscany, Caf Tour & Travel Team
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
Dear Bonnie, Thank you very much for your wonderful review! We’re delighted to hear that you enjoyed the tour and appreciated Sandro’s knowledgeable and pleasant guidance through the Chianti region. It’s great to know that the lunch, along with the Chianti wines and Vin Santo tasting, made the experience even more special. We’re also very happy that you enjoyed the visit to the Siena Cathedral with Lucia, she will be thrilled to know her detailed explanation made a strong impression. Thank you for choosing our tour and for taking the time to share your feedback! Best regards from Caf Tours & Travel
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.
Good Morning from Caf Tour & Travel, Dear Stepha, Thank you for sharing your detailed feedback. We’re pleased to know that you enjoyed the destinations and appreciated our guide’s friendliness and professionalism. However, we’re truly sorry that other aspects of the experience, such as the group size and lunch at the winery, did not fully meet your expectations. This specific tour is designed to offer a comprehensive overview of Tuscany’s highlights in one day, which can attract a larger number of participants, especially during high season. Your comments about the winery visit and logistics are invaluable, and we will share them with our local partners to help improve comfort and organization. We hope to have the chance to welcome you again on another tour, perhaps one of our smaller experiences, for a more relaxed and tailored day in Tuscany. Warm regards from Florence, The Caf Tour & Travel Team
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!)
Good Morning from Caf Tour & Travel, Dear James, Thank you very much for taking the time to share your thoughtful review. We’re so pleased to hear that you had a lovely time exploring San Gimignano, Siena, and Monteriggioni, and that you enjoyed the lunch and wine tasting at the Tuscan winery. Costantino will be delighted to know that you appreciated his passion, humor, and engaging explanations, he truly enjoys bringing the spirit of Tuscany to life for our guests. We also appreciate your comment about the bilingual format and will certainly take it into consideration. We hope to welcome you again soon for another memorable experience in our beautiful region. Warm greetings from Florence, The Caf Tour & Travel Team
