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(182)
I really enjoyed this trip and it was a nice break from being in the city. It's a typical bus tour where everyone piles on from one stop to the next, but it gives you a great opportunity to visit some interesting sites. All the stops were great, including lunch at a vineyard with wine tasting. However, Siena was probably our favorite stop. Beautiful city and full of energy as the city prepared for the upcoming Palio di Siena horse race.
Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for sharing your #TuscanyLife experience! We’re delighted that the day offered you a refreshing break from the city and the chance to discover Siena and the beautiful medieval towns of Tuscany. It sounds like Siena truly stole the show, especially with the city buzzing ahead of the famous Palio di Siena! We’re also happy you enjoyed the vineyard lunch and wine tasting, and hope to welcome you back for another taste of the Tuscan lifestyle. Warmest wishes from Tuscany, Caf Tour & Travel
This was such a fun day trip through the Tuscan region, with wine tasting, a delicious lunch, and plenty of beautiful scenery along the way. The highlight for me was definitely spending the afternoon exploring Siena. A great way to experience the best of Tuscany in one day!
Good Morning from Caf Tour & Travel, Dear Aidan, Thank you for your fantastic review! We’re thrilled that you enjoyed your day discovering Tuscany, from the beautiful scenery and wine tasting to the delicious lunch. We’re especially happy that exploring Siena was the highlight of your experience—its history and atmosphere truly make it unforgettable. We hope to welcome you back to discover even more of Tuscany! Arrivederci from Tuscany, The Caf Tour & Travel Team
The tour was wonderful, we loved San Gimignano with its amazing towers. We had our own free time to explore all the stops. Our guide Ricardo was excellent. He gave us lots of interesting information on the places we were visiting and made sure we all knew the time and place we were meeting. He guided us through Sienna. The wine tasting was fabulous, we tasted 4 glasses of wine , 2 Spumante. The food was great. This is an 11 hour trip but it was only a little walking. We loved it. Christina helped Ricardo with the tour. It was really good value for money and I highly recommended doing it. Bellissimo!
Thank you Sarah for such a generous and detailed review! We’re so pleased that the day gave you the freedom to explore while still feeling well guided throughout. Riccardo and Cristina will be delighted by your kind words, and it’s wonderful to know the wine tasting and lunch added so much to the experience. Warm greetings from Tuscany!
Excellent tour. Special thanks to our bus driver, Alice, and tour guides Fabi and Louisa. Cathedral in Siena worth paying extra. Beautiful scenery, tasty food and wine, shopping lover's dream. Grazie!
Grazie mille for this lovely review! We’re so pleased that Elis, Fabi, and Louisa helped make the day such a success. Siena clearly made a strong impression, and your words will be very helpful to future travelers considering the Cathedral visit. Thank you again for sharing your experience, and warm greetings from Tuscany!
Experiencing a long table for lunch with new found friends while tasting several wines & eating authentic Italian food was much more than expected. I even bought Biscotti & Pasta! Discovering Siena on foot, seeing the Cathedral & revisiting the history & learning the culture of the city is priceless!
This is exactly the kind of experience we love to hear about, sharing a long table with new friends, tasting local wines, enjoying authentic Italian food, and even taking a few delicious souvenirs home! We’re also so happy that Siena, its Cathedral, and its history left such a strong impression. Thank you for letting us be part of such a memorable day in Tuscany! See you soon, Zoe!
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.
Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for sharing such thoughtful feedback about your Tuscany experience with us. We are very pleased to know that you appreciated the organization of the itinerary and enjoyed the balance between each stop, allowing you to fully experience the beauty and history of extraordinary places like Siena, San Gimignano, and the Chianti countryside. We are especially happy to hear that Gabriel and Fabi helped make the journey smooth and enjoyable, and that Fabi’s knowledge and ability to communicate in multiple languages added even more value to your day. Tuscany offers a truly unique combination of culture, landscapes, and authentic hospitality, and we hope to welcome you again very soon. Kind regards from Florence, Caf Tour & Travel Team
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
