Siena, Cortona, Montepulciano & Val D'Orcia in a Small Group Tour





Description
Explore in the comfort of a 8 seat van the most beautiful Tuscan towns made famous through films together with a passionate local driving guide. Enjoy lunch overlooking the rolling hills of Montepulciano while tasting famous wine. Wander the winding streets of Cortona walked by Diane Lane in "Under the Tuscan sun", watch out for the vampires of the Twilight saga " New Moon" in Montapulciano and taste the famous Noble of Montepulciano wine. Explore the locations made famous by Michelle Pfieffer in "A Midsummer night's dream" and Ralph Fienes in " The English patient". Spot the iconic rolling hills of Tuscany from " Letters to Juliet" and enjoy a taste of the local lifestyle by sampling fine local wine, cheese and other products from the region.
Tour Options
Itinerary
Meet your local tour leader by Porta Romana, central Florence at 07:45am ready to leave by 8:00am. Travel for an hour and a half on board of a private 8 seat mini-van through the beautiful Tuscan countryside enjoyed by generations on the movie screen while listening to stories and info about the area from your tour leader.
Our first destination is the charming hilltop town of Cortona, famous for its olive groves and immortalized by Diane Lane in Under the Tuscan Sun. Explore independently the town with its narrow streets, artisan stores, and landmarks featured in Frances Mayes' beloved novel. Who knows, you might even start your own Italian love story!
Next, we travel just 40 minutes from Cortona to a picturesque local farm nestled in the heart of Tuscany. Here, Cinta Senese pigs roam semi-wild, thriving on natural feed. Stroll among olive trees and vineyards before savoring the farm's exceptional products in a tasting board we have organised for you —cured meats and bruschetta made from garden-fresh ingredients, paired with their own wine. This unforgettable experience will leave lasting memories.
We then head to the famous MONTEPULCIANO , where vampires converge in Twilight Saga: New Moon. This beautiful walled town is also home to the renowned Montepulciano DOCG wine. Your tour leader will provide during the journey local insights, information about specific film scenes, and other attractions of Montepulciano, allowing you free time to explore the town at your leisure. Located near the entrance of the village is a 14th-century underground cellar where you will be able to enjoy a complimentary tasting of local wines and products they offer to the guests.
After exploring Montepulciano, unwind in our comfortable van as we journey through the breathtaking Val d'Orcia. Marvel at the stunning landscapes, rolling hills, and iconic cypress trees. With ample time to relax, you can fully immerse yourself in the beauty of this enchanting region.
Our last stop is the Medieval town of Siena, the backdrop for movies like Letters to Juliet and Stealing Beauty. Prepare to be amazed by Siena's charm, with its narrow streets, local artisans, and medieval squares glowing in the setting sun. Your tour leader will escort you from the parking spot to the main piazza passing by the center. From there you will have 1hour approx free time to wander around.
We will have then 1 hour approx ride and we will finally head back to Florence for approximately 8:00pm
Highlights
What's included
Traveller Ratings
Important Information
- Not recommended for pregnant travelers
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- Please note that this tour involves a fair amount of driving due to the distance of these villages.
- The order of the stops may change to ensure the best experience possible
- Please note, the tour requires a minimum of 4 participants. If not reached, a private option with a supplement will be offered.
- Not recommended for travelers with walking disabilities
Reviews(122)
This trip was the best for me 🫶🏾🥺🙏thanks so much to Alberto!!!! He is amazing
Wonderful! Highly recommend!
Amazing day with Antonello! Beautiful trip to Siena, Montepulciano and Cortona!
Tony was an amazing tour guide! Gave us a great day of family adventures
Wonderful day drip with family. Beautiful scenery
It was wonderful. Very interesting. The lunch was fantastic. The guide, Tony was very knowledgeable. Long but worthwhile day. You will see beautiful places
This was a wonderful experience. A true highlight of our 2+ week honeymoon. We loved our guide Ned! He did a great job leading us through all of these amazing places while being very informative and fun to hang out with for the whole day. The visit to Roberto’s farm in Val D’Orcia was very special; such hospitality in such a magical place. Highly recommend!
Thank you so much for your beautiful review! We’re truly honored to hear that this experience was one of the highlights of your honeymoon. It’s wonderful to know that your tour leader Nedas made the day both informative and enjoyable while guiding you through such amazing places. We’re especially happy that your visit to Roberto’s farm felt so special and memorable. The hospitality and beauty of that area truly make it magical. Thank you again for choosing to spend part of your honeymoon with us, and we wish you both many more wonderful adventures together!
Ned is excellent ! Love this tour! I highly recommend
Thank you so much for your kind words! We’re thrilled to hear that you loved the tour and had such a great experience with your tour leader Nedas. Your recommendation truly means a lot to us. We hope to welcome you back for another unforgettable Tuscany adventure soon!
Giovanni was an exceptional tour guide. He was extremely informative and had a great sense of humor. We all loved him, and I would recommend his service to any group traveling to Italy! Bravo Giovanni!
Thank you for the fantastic feedback! We’re so happy to hear that your tour leader Giovanni made such a great impression, his knowledge and sense of humor truly make the experience special. We’ll be sure to pass along your “bravo” to him! Hope to welcome you again on another adventure in Italy!
Great day out, go to ti amo gelato!
Thank you for the cheerful review! We are glad you enjoyed your tour with us.



