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
4.4
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144 traveller ratings
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Worth the money. Must do.
Rudy_M, Sept 2025
Wonderful trip with a great tour guide Veleaka. This was an 11hr tour and we were never bored. It was a leisurely trip with the best views of Tuscany we saw while in Italy.
Response from Host, Sept 2025
Dear Customer, Thank you for sharing your feedback with us! We’re thrilled to hear that you had a wonderful time on the tour and that Valeska made such a positive impression on you. Your feedback means a lot to us, and we hope to welcome you on another adventure soon! Best regards, My Tour In Italy
Tuscany tour
Thuy_T, Jun 2025
We enjoyed our day tour to the vineyards and the rides of Tuscany region !!! Highly recommended this tour if you have a few days to Siena or just one day to spare from Florence.
Response from Host, Jun 2025
Dear Customer, Thank you for sharing your feedback with us! We're thrilled to hear you enjoyed your day exploring the vineyards and the beautiful Tuscany countryside. We truly appreciate your recommendation and hope to welcome you again in the future! Best regards, My Tour In Italy.
First winery was nice...
Suzi_M, Jun 2025
First winery was nice though it was an extra $20 for lunch which was very confusing. Tour guide wasn’t friendly and slept a lot. Second winery was horrible.
Response from Host, Jun 2025
Dear Customer, Thank you for sharing your feedback with us! We’re sorry to hear that some aspects of the tour did not meet your expectations, especially regarding the additional lunch cost and your experience with the guide and the second winery. Your feedback is important to us and will be shared with the team to improve future tours. We appreciate your honesty and hope to provide you with a better experience in the future. Best regards, My Tour In Italy.
Beautiful scenery
gwarnershoe54, May 2025
The country side was beautiful and the two wineries were amazing and different. There were some mix ups in our visits and timing but our tour guide handled it well. Highly recommend this tour
Response from Host, May 2025
Dear Customer, Thank you for sharing your feedback with us! We’re glad you enjoyed the countryside and wineries, and that our guide made the experience smooth despite the timing mix-ups. We truly appreciate your recommendation! Best regards, My Tour In Italy.
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.