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Private Tour from Florence: Marvel at Medieval Tuscan Hill Towns, Cortona & Montepulciano
5.0
15 Ratings
Cortona
Embark on an exclusive private tour from Florence and explore the enchanting medieval Tuscan hill towns of Cortona and Montepulciano. Marvel at their beauty, visit iconic film locations, and indulge in the world-famous Vino Nobile wine.
Embark on an exclusive private tour from Florence and explore the enchanting medieval Tuscan hill towns of Cortona and Montepulciano. Marvel at their beauty, visit iconic film locations, and indulge in the world-famous Vino Nobile wine.
Duration:
8 hours
Cancellation:
24 hours
Highlights
- Duomo di Cortona - Meet our English-speaking driver at your hotel and embark on a journey in a comfortable Mercedes-Benz to the stunning town of Cortona. Enclosed by ancient stone walls from the Etruscan and Roman eras, Cortona is perched atop a hill approximately 600 meters (1968 feet) above sea level. This elevated position provides breathtaking…
- Duomo di Cortona - Meet our English-speaking driver at your hotel and embark on a journey in a comfortable Mercedes-Benz to the stunning town of Cortona. Enclosed by ancient stone walls from the Etruscan and Roman eras, Cortona is perched atop a hill approximately 600 meters (1968 feet) above sea level. This elevated position provides breathtaking views of the surrounding valley and Lake Trasimeno. The town gained popularity over the past decade due to Frances Mayes’ book, Under the Tuscan Sun, and its film adaptation starring Diane Lane. The story’s protagonist falls in love with Cortona, its residents, and the villa Bramasole, which she buys and renovates. Take some time to relax or explore the area; your driver will recommend the best activities.
- Piazza Grande a Montepulciano - Depart at 11:30 AM for a delightful light lunch at a family-owned winery. Then, enjoy a relaxing 30-minute drive through the hills to Montepulciano, surrounded by breathtaking landscapes. Your driver can stop anytime you wish to take photos. Arrive in the charming town of Montepulciano around 2 PM. This medieval hill town is renowned for its elegant Renaissance palaces, ancient churches, charming squares, and hidden corners. Montepulciano gained fame as a filming location for the Twilight saga’s New Moon sequel, attracting many visitors. Strolling through Montepulciano is the best way to appreciate its beautiful landmarks and enjoy stunning views of the surrounding vineyards, which produce the famous Nobile wine available for tasting in numerous wine shops within the city walls.
What's Included
- Hotel pickup and drop-off
- Private tour
- Professional driver/guide
- Transport via Mercedes-Benz V Class with AC
- All taxes, tolls, and parking fees included
- Onboard WiFi access
- Hotel pickup and drop-off
- Private tour
- Professional driver/guide
- Transport via Mercedes-Benz V Class with AC
- All taxes, tolls, and parking fees included
- Onboard WiFi access
What's Not Included
- lunch
- Gratuities
- lunch
- Gratuities
Additional Information
Embark on an exclusive private tour through the picturesque Tuscan countryside, where golden fields, olive groves, and cypress-lined roads guide you to two of the region’s most captivating medieval hill towns. In Cortona, a place of timeless allure and renowned from the film Under the Tuscan Sun, explore the narrow stone streets and enjoy panoramic…
Embark on an exclusive private tour through the picturesque Tuscan countryside, where golden fields, olive groves, and cypress-lined roads guide you to two of the region’s most captivating medieval hill towns. In Cortona, a place of timeless allure and renowned from the film Under the Tuscan Sun, explore the narrow stone streets and enjoy panoramic views that extend endlessly across the valley. The adventure continues to Montepulciano, majestically situated on a ridge, where every turn reveals breathtaking vistas over the Val d’Orcia and Val di Chiana — a perfect blend of Tuscany’s beauty and history.
- FOR WINE LOVERS: IS POSSIBLE TO ADD ON THIS TOUR THE VISIT OF A TOP RATED WINERY. PLEASE ADVISE AT THE TIME OF THE BOOKING
- Dress code is casual
- Comfortable shoes
Location
Duomo di Cortona
Piazza del Duomo Vecchio 1,
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
5.0
(15 Ratings)
5 stars
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1 star
Christine_m
Oct 17, 2025
Our driver, Luca, was... - Our driver, Luca, was amazing! He shared so much history about Italy and Tuscany. His knowledge, friendliness, and politeness was beyond anything we expected. I highly recommend this tour!
Review provided by Viator
George_v
Sep 7, 2025
Alessandro the Great - What a wonderful way to experience Tuscany. Alex went above and beyond to make our day spectacular. We had another tour cancel the day before and Alex stepped up and made a day even better with a private tour, unique wine tastings and suggestions and he was super patient with us as we constantly tasted and bought wine. What a day. Thank you Alex.
Review provided by Viator
Charles_i
Sep 6, 2025
A Charming Day in Cortona - Our tour guide was Massimo and he was terrific in several ways, the first of which was his careful and relatively slow driving. This made the travel quite comfortable, especially for our family members who volunteered for the van’s third row. From our perspective, Cortona is the nicest Italian town we visited, and the other way Massimo excelled was by letting us stay much longer instead of traveling on to Montepulciano as the tour design called for. So as Massimo returned us to our Villa, my family agreed that we very much enjoyed the day!
Review provided by Viator
Charles_i
Sep 5, 2025
A Delightful Visit to Cortona & Montepulciano - Alessandro was our guide and he expertly guided us through a visit to the charming Tuscan towns of Cortona & Montepulciano. Ours was a private tour and Alessandro was attentive to our wishes which allowed us to choose how much time to spend in each locale. As he returned us to our Villa, all agreed that we very much enjoyed the day!
Review provided by Viator
Adamrt3695mn
May 5, 2025
Amazing time. A definite must see. - Alessandro was amazing. He was very knowledgeable about the area and was very friendly. He gave us areas that we should visit while in Cortona and also gave us recommendations for places to see for the remainder of our trip. I would definitely recommend Tuscany in Tours to everyone.
Review provided by Tripadvisor
Robyn_b
Dec 12, 2024
Terrific Driver & Guidr - Massimo is a wonderful driver and guide. He knew how to fill our time - giving us plenty of spare time to explore. It was a most enjoyable experience. Highly recommend him.
Review provided by Viator
Jason_c
Aug 23, 2024
5 Stars are not enough! - Our Tour guide and driver Luca was excellent! We were able to see Cortina, Montepulciano and a Beautiful Wine Vineyard on our day trip from Florence.
Review provided by Viator
Richard_l
Jun 23, 2024
Alessandro is AWESOME! - Alessandro was AWESOME! Cortona was nothing short of stunning and Montepulciano was completely charming. If I ever find myself in Tuscany again I would totally do this tour and you should too!
Review provided by Viator
Alan_b
May 16, 2024
Perfect day, perfect guide - Alex was fantastic and made it perfect. He was very knowledgeable on not just the two towns, but Italy in general. The day was wonderful!
Review provided by Viator
Jenny
May 5, 2024
Great option to see the Tuscan countryside - I took two separate full-day tours with Tuscany In Tour; a tour of the Val d'Orcia region that I customized to my own tastes, and a tour of Cortona and Montepulciano.. Alex was my driver for both tours. He was a great driver and was very good at communicating both before each tour and during the days about when to move from location to location. For the second tour we started in Cortona and moved on to Montepulciano around lunch time. Each town was charming and beautiful, and I was happy with the amount of time I had in each one. Alex was also happy to point out a number of beautiful photo spots along the drives and stop so I could take photos. If you want to see the Tuscan countryside but don't want to drive yourself (or join a large group tour) Tuscany In Tour is a professional and enjoyable company to work with and I highly recommend them.
Review provided by Tripadvisor
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