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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
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
Jana_w
Mar 21, 2024
A wonderful day and great tour! - We had a wonderful day! Our driver and guide for our private tour was excellent…so kind and made our trip extra special! The country side was beautiful and he took us to a winery for wine tasting!
Review provided by Viator
Amy_r
Feb 22, 2024
Travel Out to Tuscan Mountain Towns - Massimo was an excellent driver and host for this activity. He was able to share historical and cultural information as we were en route and made the calls needed to add in a local winery visit.
Please note this is NOT a guided tour of Cortona and Montepulciano. The driver takes you to the locations, and you are on your own to visit as you see fit. For me, this was perfect, as I like to wander on my own.
I appreciated the door-to-door service and the confirmation communication the day before.
Review provided by Viator
Tracycobb
Jan 30, 2024
Must do - I don’t usually do private tours. Massimo was so pleasant to talk to, informative and flexible. We made an unplanned stop for wine tasting. I really enjoyed this tour. It was a beautiful day and peaceful break from the busy city.
Review provided by Viator
Angelica_r
Dec 9, 2023
Gorgeous Views!!!! - Nothing short of AMAZING!!! Weather was cold and windy on the hilltop towns, but it was still gorgeous. Wine and food was amazing and we even visited a local winery. Our driver, Massimo, was awesome and very knowledgeable. We highly recommend this private tour. Will not disappoint.
Review provided by Viator
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