Small Group Tuscany Tour Montepulciano, Montalcino and Cortona
Description
Embark on a captivating journey from Florence to discover Tuscany’s most iconic gems. Begin in Cortona, a hilltop village of Etruscan origin made famous by Under the Tuscan Sun, where you’ll explore medieval charm and visit a master ceramic artisan’s workshop (or traditional artisan shops). Continue to Montepulciano for a tasting of five fine wines, including the prestigious Nobile and Brunello di Montalcino, and enjoy a light lunch in a historic underground cellar (if option selected). Then, travel through the stunning Val d’Orcia, a UNESCO World Heritage Site, with scenic stops including filming locations from The Gladiator. End in Montalcino, a medieval town with a 14th-century fortress and breathtaking views, where you can savor the region’s rich wine culture. Return to Florence with lasting memories of Tuscany’s timeless beauty, history, and flavor. (*) if not available, it will be replaced with a visit to authentic artisan shops, with typical works Tour order may vary
Tour Options
Itinerary
Starting from Florence, the journey takes you to Cortona, one of the most ancient and charming villages in Tuscany. Perched on a hill in the Val di Chiana and made famous by the movie Under the Tuscan Sun, Cortona boasts Etruscan origins, evidenced by the imposing walls surrounding it, which date back to the 4th century BC. The village offers a perfect blend of medieval architecture, authentic atmospheres, and local culture, making it an unmissable destination for those seeking timeless beauty and authenticity.
The next stop is Montepulciano: in this captivating Renaissance town, you’ll have the opportunity to taste the prestigious Nobile di Montepulciano wine in a charming and historic underground cellar, learning the secrets of its production and having the chance to purchase bottles at attractive prices. After the included tasting, you’ll have free time for lunch (not included) at a typical trattoria and to explore the beauties of the historic center, famous as the set for films like New Moon and the series Medici: Masters of Florence featuring Dustin Hoffman and Richard Madden.
As you continue toward the Val d'Orcia, you will enter the heart of one of Tuscany’s most scenic areas, where you can admire the iconic landscapes of rolling hills dotted with cypress trees, known worldwide for their ineffable beauty and recognized as a UNESCO heritage site. Along the way to Montalcino, you will spot the settings of famous films like The Gladiator—a perfect opportunity for taking iconic photos.
The final stop is Montalcino, a charming hilltop town surrounded by the rolling landscapes of the Val d’Orcia. Known worldwide as the home of Brunello, one of Italy’s most prestigious wines, Montalcino offers an authentic taste of Tuscan tradition, history and beauty. Enjoy its medieval atmosphere, scenic views and deep connection to local wine culture.
Highlights
What's included
Traveller Ratings
Important Information
- Public transportation options are available nearby
- Specialized infant seats are available
- Travelers should have at least a moderate level of physical fitness
- The tour is confirmed with minimum 4 participants
- (*) if not available, it will be replaced with a visit to authentic artisan shops, with traditional and typical works of the village
- No vegetarian or gluten-free options available
Reviews(30)
Excellent experience, a beautiful trip with stops in beautiful and historic cities. Special thanks to our guide, Francesco, for excellence, attention and service.
Good Morning from Caf Tour & Travel, Dear Alexandre, Thank you for your wonderful review! We’re delighted that you enjoyed discovering some of Tuscany’s beautiful historic towns and that Francesco’s attention and professionalism made your journey even more special. We’ll be happy to share your kind words with him. We hope to welcome you back to Tuscany again soon! Warm regards from Tuscany, The Caf Tour & Travel Team
Francesco was a very good tour guide. He was very friendly and kept us updated with the timing. Knowledgable.
Good Morning from Caf Tour & Travel, Dear Customer, Thank you for your kind words! We’re pleased to know that Francesco’s friendly approach, knowledge, and careful attention to the timing helped make your day enjoyable and smooth. Exploring Montepulciano, Montalcino, and Cortona is a wonderful way to discover a quieter side of Tuscany. We hope to see you again! Kind regards from Italy, The Caf Tour & Travel Team
Francessco was a fabulous guide! Informational and personal
Good Morning from Caf Tour & Travel, Dear Chloe, Thank you for your lovely review! We’re delighted that Francesco made your journey through Tuscany’s charming towns both informative and personal. These historic places have so many stories to tell, and we’re happy you enjoyed discovering them with us. We hope to welcome you back for another beautiful Tuscan experience! Arrivederci and see you soon, The Caf Tour & Travel Team
Great day visiting some of the lesser known places in Tuscany, perfect if you want to explore more of Tuscany outside of Sienna etc.
Good Morning from Caf Tour & Travel, Dear Kate, Thank you for sharing your experience! We’re delighted that you enjoyed discovering some of Tuscany’s lesser-known gems beyond the most famous destinations. Montepulciano, Montalcino, and Cortona offer a wonderful glimpse into the authentic beauty and character of the region. We hope to welcome you back to explore even more of Tuscany! Warmest wishes from the Tuscan countryside, The Caf Tour & Travel Team
Marta is a great guide. She’s kind, thoughtful and personable. Our day was extremely hot and she thought ahead about keeping us cool and in the shade. Notably, she asked if we’d like to get a shuttle up the steep hills of Montepulciano and we all agreed. It really added to the experience, eliminating the long climb to the top and saved us all the heat and exhaustion of walking. For future tours I would say it’s a must to be included in all your tours to Montepulciano. My husband and I especially enjoyed the wine tasting with a light lunch. Cortona and Montalcino were lovely and worth the stops. Rogero is a courteous and good driver. This tour was perfect to give my husband and I a brief introduction to the area so we can be prepared to return with our family.
Good Morning from Caf Tour & Travel, Dear Teresa, Thank you for your thoughtful and detailed review! We're delighted that Marta's care, attention, and thoughtful suggestions helped make your day comfortable despite the summer heat. It's wonderful to hear you enjoyed Montepulciano, Montalcino, Cortona, and the wine tasting, and we'll gladly share your appreciation with both Marta and Ruggero. We hope to welcome you and your family back to Tuscany very soon. Warm greetings from Italy, The Caf Tour & Travel Team
We booked this tour for our family of 4, 2 adults & 2 kids. Upon arrival, the tour operator informed us they did not have confirmation of our 2 kids' reservations. We did not get to go on the tour and spent over $830 for the four of us, which was paid in full months prior to the date of the tour. We were told by the tour operator that their "system" must have had an issue and there was simply not enough space for our family of four. The exact same thing happened to the family we were traveling with - the 2 adult were confirmed and the tour operator did not have their child confirmed. Since all 3 kids are minors (ages 14 and under) we were not going to leave them in Florence for the day while the adults left. Additonally and suspiciously, since this was to be a small group tour and there was a large Mercedes van being worked on right behind the tour operator, we are wondering if they simply couldn't take us due to mechanical issues with the vehicle. Of course, that is speculation on our end. Since reaching out to Viator about this, we have been given the runaround, told that the tour operator said we arrived late to check in for the tour (which is not true), and that because of that, we were in violation of the policy and thus everyrthing was out fault. Also, we weretold we will not receive a refund. At the end of the day, regardless of what time we had shown up, the tour operator told us there was no room for our children, nor our friend's child. That is the bottom line. We should not have to pay for something when what occurred was in no way our fault. Needless to say, after planning a 12-night trip to Italy and being excited for this and all other experiences we had planned, including 4 other tours booked through Viator, this was not only disappointing, but Viator has handled this matter egregiously and unprofessionally. I will never book anything with Viator again unless they make this right.
Dear Jessica, We are sorry that this experience did not meet your expectations. However, we would like to clarify several important points, as the description provided in this review does not accurately reflect what occurred. First, the refund was not declined because you arrived at the meeting point after the scheduled departure time, when the tour had already left. As clearly stated in the terms and conditions accepted at the time of booking, late arrival is treated as a no-show and does not entitle guests to a refund or rescheduling. We acknowledge that a system issue affected the visibility of the children’s reservations, and we regret that this technical error occurred. We are reviewing the matter internally. Nevertheless, even without this issue, your late arrival meant that participation would no longer have been possible, as the tour had already departed. Therefore, the refund policy would have applied in exactly the same way. Regarding the Mercedes van mentioned in the review, it belonged to another tour operator and was entirely unrelated to your booking. Unfortunately, the presence of another company’s vehicle near the meeting point does not mean that it was available for our guests, nor could we simply place passengers booked on our tour into another operator’s vehicle. We fully understand that missing a planned excursion is disappointing. At the same time, our policies regarding punctuality, missed departures, refunds and rescheduling are clearly communicated before booking and apply equally to all guests. We regret the technical booking issue, but the decisive factor in this case remains that late arrival. Warm regards
Excellent tour of Tuscany! Riccardo was an excellent guide and provided lots of information about each town we explored and made it fun to learn. He provided good recommendations for food/shopping. The bus was very comfortable and clean. Be prepared for quite a bit of driving between towns as well as walking up/down hills in each town, it's a full day! Totally worth the trip to see these areas outside of Florence!
Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for sharing such a wonderful review of your Tuscan experience with us. We are delighted to hear that Riccardo helped make your journey both enjoyable and enriching, sharing stories, local insights and recommendations that added even more value to the day. Exploring gems like Montepulciano, Montalcino and Cortona truly offers an authentic taste of Tuscany, and we are so happy you found the experience worth every moment. We hope to welcome you again soon for more unforgettable discoveries across beautiful Italy. Warm greetings from Tuscany, Caf Tour & Travel Team
Really enjoyed the tour. We did a small tour - us 4 and 2 others. Our guide, Leo, was amazing. Really informative, kept us up w everything throughout the tour. Having a guide like him really made the tour a great experience. The three towns were beautiful. The wine tour was cool as well. Alessandra (wine tour guide) was fun and jovial. Thus far this was one of our favorites.
Good Morning from Caf Tour & Travel, Dear Customer, Thank you for your wonderful review! We are delighted to hear that this became one of your favorite experiences so far. Leo will be thrilled to know that his knowledge, enthusiasm, and attention throughout the day helped make the tour so memorable. We are also happy that you enjoyed the beautiful towns, the wine experience, and Alessandra’s engaging and cheerful approach. We hope to welcome you back soon to discover even more of Tuscany’s hidden treasures. A warm arrivederci from Italy, Caf Tour & Travel
Fantastic great for people with mobility issues. Lao was knowledgeable and easy going. Really knew how to take care of his people. Would do again.
Good morning from CAF Tour & Travel! Dear Kathleen, We are very pleased to hear that you had an enjoyable and comfortable day in Tuscany and that Leo provided attentive and knowledgeable care throughout the tour. We hope to see you again in the future for another experience with us. Best wishes, CAF Tour & Travel Staff
We had an absolutely wonderful time on our small group tour of Cortona, Montepulciano, and Montalcino! We had the opportunity to explore the towns and learn their interesting history. To add to the experience, we had a great wine tasting in Montepulciano. Our guide, Leo, was incredibly helpful and knowledgeable. He shared fascinating insights into the region’s history and guided us to some fantastic dining and shopping spots. Thank you, Leo, for making our trip an unforgettable experience!
Good morning from CAF Tour & Travel! Dear Julio, Thank you very much for your lovely review! We are delighted to hear that you had such a wonderful experience exploring Cortona, Montepulciano, and Montalcino. It’s great to know that Leo’s knowledge and recommendations helped make your trip even more special. We truly appreciate your kind words and hope to welcome you again soon for another unforgettable Tuscan adventure! Best regards, CAF Tour & Travel Staff
