11 hours
E-voucher
English
Overview
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
Operated by
CAF Tour and Travel
Ratings & Reviews
Average Rating
5
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11 traveller ratings
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Authentic Tuscany
Fred_sckn, Apr 2025
The tour is well planned and it shows a Tuscany free of mass tourism. Cortona, with the medieval architecture and the ceramic workshop and Montalcino with its fortress were the main highlights. The Montepulciano wines were super tasty too! RECCOMENDED!
Response from Host, Apr 2025
Dear Fred, Thank you so much for your kind words and for taking the time to share your experience! We're delighted to hear that you enjoyed exploring the more authentic side of Tuscany with us. Cortona’s medieval charm, Montalcino’s historic fortress, and the exquisite wines of Montepulciano truly make for a memorable journey, and we're thrilled that you found them to be highlights of your tour. Your recommendation means a lot to us, and we hope to welcome you back for another unforgettable adventure in Italy! Best regards,
Jewels of Tuscany
pignad, Apr 2025
A wonderful experience to discover the hidden treasures of Tuscany. Cortona is a small village full of history and traditions, ideal for a stroll through its narrow streets. The journey continues towards Montepulciano and Montalcino, famous for their red wines. Not to mention the breathtaking panorama. Highly recommended. Friendly and highly professional staff.
Response from Host, Apr 2025
Dear Customer, Thank you so much for your kind review! We are thrilled to hear that you had such a wonderful experience discovering the hidden treasures of Tuscany. Cortona, Montepulciano, and Montalcino are indeed charming places with rich history, beautiful streets, and stunning views. It’s great to know you enjoyed the tour and our friendly, professional staff. Your recommendation means a lot to us, and we hope to welcome you back on another adventure in the future! Warm regards
Cortona, Montepulciano, Montalcino three hidden gems!
Chrustal, Apr 2025
I've really appreciated this tour, great value for money! it was well scheduled and organized , beautiful places! We travelled toward the southern part of Tuscany visiting Cortona, Montepulciano and Montalcino, three hidden gems! The staff transmitted us love , history and passion for those places! We discovered Cortona , an old etruscan city with its tradition of making "ceramica", and many others artisanal shops. We had the second stop in Montepulciano with the wine testing included in a stunning underground cellar and last but not least stop in Montalcino. Breathtaking views, hospitality, history and traditions the highlights of this tour. Thanks!
Response from Host, Apr 2025
Dear Customer, Thank you so much for your kind words and for taking the time to share your experience! We are delighted to hear that you enjoyed exploring the hidden gems of southern Tuscany with us. Our team takes great pride in sharing the history, traditions, and beauty of these incredible places, and it’s wonderful to know that this passion resonated with you. We’re especially happy that you appreciated the well-planned itinerary, the artisanal charm of Cortona, the wine tasting in Montepulciano, and the breathtaking views of Montalcino. Your satisfaction is our greatest reward! We hope to welcome you on another unforgettable journey in the future. Best regards,
Amazing Tuscany
RicTheWanderer, Apr 2025
I really enjoyed this tour, stunning sceneries and a perfect way to discover hidden gems of Tuscany, where you still find an authentic atmosphere. We also tasted amazing local wines in Montepulciano, the tour was well organized and the staff was knowledgeable and very kind, I recommend it.
Response from Host, Apr 2025
Dear Ric, Thank you so much for your wonderful review! We’re delighted to hear that you enjoyed the tour and had the opportunity to discover the hidden gems of Tuscany. It’s fantastic that you appreciated the authentic atmosphere and breathtaking scenery, as well as the wine tasting experience in Montepulciano. Our team takes great pride in providing well-organized tours and sharing their knowledge with our guests, so it’s truly rewarding to hear your kind words. We sincerely appreciate your recommendation and hope to welcome you on another adventure in the future! Best regards,
Itinerary
Cortona
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.
2 hoursMontepulciano
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.
2 hoursVal D'Orcia
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.
20 minutesMontalcino
The final stop is Montalcino, home to Brunello, one of the world’s most renowned wines. Here, after exploring the quaint historic center, we’ll visit a renowned winery, where you’ll taste Brunello and Rosso di Montalcino wines, immersing yourself in the storytelling of the region’s rich winemaking traditions. Before returning, you’ll have the chance to purchase fine wines directly from the producer—an opportunity not to be missed.
2 hours
Experience
Inclusions
- If option selected: Light Lunch in a unique and exclusive setting, an historic & underground cellar
- Opportunity to purchase wines and local products you have enjoyed (worldwide delivery available)
- Wine tasting including Vino Nobile di Montepulciano in a historic underground cellar
- Licensed Tour Escort
- Caf Tour’s Team Assistance at the meeting point
- Ceramic decoration demonstration (*)
- Transport by air-conditioned Mini Coach
- Visit Montalcino and learn the story behind one of Italy’s most famous wine regions
Exclusions
- Hotel pick-up and drop-off
Additional 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
Guide Languages
English
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.