11 hours
E-voucher
Multiple
Overview
Start with 8:30am hotel pickup, depending on the time of year. As the sights of Siena slip into the distance, you’ll notice the landscape turn into the undulating hills of Tuscany.
Your first stop in the region is the beloved hill town of San Gimignano, a UNESCO World Heritage Site. Enjoy free time here to wander the streets of its historical center, gazing at the medieval architecture, towers, piazzas, and artisan shops. San Gimignano produces the renowned vernaccia wine, and you’ll find plenty of enoteche (wine shops) around the streets.
Then, travel into the Val d’Orcia region of Tuscany where the winemaking village of Montalcino awaits. Next, you’ll head to the historic fortress town of Monteriggioni. Stop at a winery for lunch and a wine tasting. Savor a light meal of local cheese and salami, paired with Chianti wine.
Taste the esteemed Brunello di Montalcino wine, and learn about the town’s winemaking traditions.
Relax on the journey back to Siena, and finish your day trip with a hotel drop-off.
Operated by
myTour in Italy
Ratings & Reviews
Average Rating
4.42
/ 5
136 traveller ratings
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Great Experience in Tuscany
marciab182, Mar 2025
Great wine tasting experiences, guide Mikaelo was very knowledgeable with history and culture of the area. My only disappointment was that we were dropped off for the towns & our guide didn’t go with us. For the cost of the tour we purchased, I was surprised. I do very much appreciate him taking us on as a tour at the last minute as our previous tour cancelled.
A nice tour, nicer if the time was adjusted
Bridget_I, Jan 2025
Our driver, Giovanni, was prompt and provided a clean vehicle but he was NOT a guide as the trip was advertised. Rather than talk about Italy, he wanted to engage about politics and his heavy smoking between stops made the van stink. Our tour left at 8:30 to get to San Gimignano. We were disappointed to arrive in the town to see nothing open. We had until 11:30 to wander but it was frustrating not to be able to go into any shops or climb the tower until 10:30 or 11. It felt like an hour and a half of wasted time. We were traveling in January, so perhaps the time of year was a factor but the company should adjust the times. We stopped for a fantastic wine experience at a Chianti winery. Leda was wonderful and it was a highlight. We also enjoyed the winery at Montalcino, but it was a lot of wine in a short time. Our final stop was a town visit in Montalcino. By now it was dark and stores and attractions were closed again. This would have been a much better trip if there was more time in the towns while things were open.
Response from Host, Jan 2025
Dear Customer, Thank you for taking the time to share your experience with us. We deeply value your feedback as it helps us to continuously improve our services. We are truly sorry to hear that your tour did not meet your expectations. It is disappointing to learn that Giovanni, our driver, did not fulfill the role of a guide as anticipated. We understand how important it is for a tour to be informative and engaging, and we will address this concern with Giovanni to ensure that our future guests have a better experience. We also apologize for the timing issues with your visit to San Gimignano. Furthermore, we understand your frustration about the shops and attractions being closed during your free time. As you mentioned, January can be a quieter time for tourism, but we will certainly review the timing of the stops to ensure our future tours are more aligned with the opening hours of local businesses, allowing guests to make the most of their time in each town. On a more positive note, we’re so glad to hear that you enjoyed the wine experiences at the Chianti and Montalcino wineries, especially Leda’s hospitality. We aim to create memorable experiences, and it’s wonderful to hear that this was a highlight of your day. We hope that despite these challenges, you were still able to enjoy some aspects of your trip. Looking forward to welcoming you back in our upcoming tours in the near future, in order to provide you a better experience, hoping we will receive a full star rate next time from you. Best regards, My Tour in Italy team.
Salute
Niallafddiancrhaghon, Oct 2024
Enjoyed the tour. Vincenzo was a charm … thank you for the intriduction to driving in Italy! Plenty of wine ???? Good company in group too.
Response from Host, Nov 2024
Dear Customer, Thank you so much for your kind words. We're so glad you enjoyed the tour, and we're thrilled to hear that Vincenzo made such a positive impression. Driving in Italy can definitely be an adventure, and we’re happy he could guide you through it! It's great to know you had plenty of wine to enjoy, and that the company in the group was enjoyable as well. We hope you’ll join us again for another memorable experience soon. Best regards, My Tour in Italy team.
Convenient having a driver.
Leisa_C, Oct 2024
Having a driver made it easy to explore these Tuscan towns. The meeting point was easy to find. You couldn’t called this trip a “guided tour” the driver gives you some information as they drive you around but they don’t accompany you in the town. Felt like we missed some of the detail you’d expect on a tour like this.
Itinerary
San Gimignano 1300
Free time in San Gimignano
1 hourCollegiata di Santa Maria Assunta - Duomo di San Gimignano
During your free time opt to visit the Cathedral of San Gimignano
15 minutesPiazza Della Cisterna
Free time in San Gimignano
15 minutesPalazzo Pubblico e Torre Grossa
Free time in San Gimignano
15 minutesStrada Statale 222 Chiantigiana
Lunch and wine tasting in a local winery in Montalcino
1 hourAdmission IncludedFortezza di Montalcino
Free time in Montalcino
1 hourSan Filippo Montalcino
Free time in Montalcino
Val D'Orcia
Spend some time in the stunning Orcia Valley
1 hour
Experience
Highlights
Inclusions
- Travel in air-conditioned minivan for up to 8 people or minibus for up to 20 people
- Expert multilingual escorts
- On-board WiFi
- Olive oil and balsamic vinegar sampling
- Snacks
- Alcoholic beverages
- Tour of 2 wine estates, one of which is exclusive + 2 wine tastings
Exclusions
- Gratuities
- Lunch
Additional Information
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Customers must be able to climb and descend stairs.
- Vegetarian option is available for the optional lunch, please advise any specific dietary requirements at time of booking
Guide Languages
English
Spanish
Italian
Cancellation Policy
A full refund will apply if you cancel more than 24 hours before the activity start time.
No refund is possible if you cancel less than 24 hours before the activity start time.