Private Tour from Florence: Marvel at Medieval Tuscan Hill Towns, Cortona & Montepulciano

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 the English-speaking driver at the hotel in a comfortable Mercedes-Benz to begin the journey to the stunning Cortona. This town, surrounded by stone walls from Etruscan and Roman times, is perched on a hill approximately 600 meters (about 1968 feet) above sea level. Its elevated position offers breathtaking views of the…
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
What's Not Included
  • 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…

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.

Customer Ratings
5.0
(17 Ratings)
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Lexi_e
Apr 15, 2026
Alex was extremely... - Alex was extremely professional and helpful. He suggested sites and experiences to make our day extra special.
Review provided by Viator
Arkady_s
Feb 14, 2026
Thank you very much to... - Grazie mille to Massimo for the wonderful day trip to Cortona and Montepulciano. He was a warm and knowledgeable host and an excellent driver, always on time. The vehicle was of great quality. Massimo gave some suggestions then let us explore each town as we wanted. We had a fantastic time. Highly recommend!!
Review provided by Viator
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
From $182
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).