Tuscany Day Trip: Explore Cortona & Montepulciano

Embark on a day trip from Rome to discover the much-adored region of Tuscany. Delve into its charming medieval villages, Cortona and Montepulciano, acclaimed worldwide for their astounding splendor. Traverse through stunning panoramas and indulge in premium local wines and exquisite cuisine. Don’t think twice, reserve your slot now!

Duration: 10 hours
Cancellation: 24 hours
Highlights
  • Cortona - Renowned as one of Tuscany’s most picturesque towns, this medieval village gained fame from the film “Under the Tuscan Sun.” Visitors will pause at the famous Villa Bramasole for photographs before heading to the town center. Here, they can explore the charming streets, relax at a café in the main square, enjoy a cappuccino, and soak in…
What's Included
  • Private transportation
  • Bottled water
  • On-board WiFi
  • In-vehicle air conditioning
  • Wine tasting
  • Parking fees included
  • All tolls covered
What's Not Included
  • Lunch
Location
Cortona
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(4 Ratings)
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1 star
Jess
Sep 29, 2025
Best e-bike experience you’ll find - Oscar was THE BEST guide! He was so knowledgeable about the history and absolutely wonderful !!! If you are looking for a great experience this is it!!! Look no further! If I could I would give 10 stars!!!
Review provided by Tripadvisor
Ronlynn_b
May 23, 2025
Great Tour of Beautiful Tuscany. - This was a great tour. Alessandro is a great guide and Driver. He looked after me very well. I ‘ ve wanted to visit Cortona since reading Frances Mayes Book “Under the Tuscan Sun” and seeing the Movie. One of the Highlights of the Tour was visiting Bramasole, The House purchased and renovated by Frances and her husband Ed which Prompted the Book and later on the Movie. To top it off Frances and Ed were in Residence and I met her when she drove out her front gate. Alessandro Wrote a wonderful guide to Cortona and Montepulciano which he gives to his guests so they get the most out of the tour. He also shows you around. After seeing Cortona we drove to Montepulciano. Where Alessandro took me to a wonderful restaurant where I enjoyed a delicious lunch with all the local specialties including the Red wine the region is famous for. afterwards we walked around the town . If you want an enjoyable day in a beautiful region of Italy. Then I recommend this tour.
Review provided by Viator
L8098gpmichelac
Nov 7, 2023
Excellent Tuscan Sun - Fantastic Tuscan countryside, beautiful historic cities explained with passion by Alessandro our guide. Super recommended, super relaxing and interesting.
Review provided by Tripadvisor
Peggymj5716rx
Oct 15, 2023
Wonderful fun in the Tuscan Sun. - This tour to Cortona and Montepulciano was exactly what I had been wanting for a Tuscany experience! Alessandro Vagnoni was a wonderful driver and guide as we drove through the countryside from Rome. In Cortona, he took pictures of us in front of the picturesque villa of Bramasole, as seen in the movie. He escorted us through the area as well as giving us time to be on our own. Montepulciano was another wonderful city where Alessandro had made reservations in advance for us for an incredibly scrumptious lunch. This 10 hour trip gave us five hours in the two cities as well as the five hours of driving in beautiful countryside seeing fields of sunflowers, vineyards and olive trees. It was a very special day in Tuscany that I will always treasure. I highly recommend this tour!
Review provided by Tripadvisor
From $242
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).