Private tour from Florence to CORTONA & MONTEPULCIANO
Description
Set out on an exclusive private tour across the rolling Tuscan countryside, where golden fields, olive groves, and cypress-lined roads lead you to two of the region’s most enchanting medieval hill towns. In Cortona, a place of timeless charm and made famous by the film Under the Tuscan Sun, you’ll wander through narrow stone streets and soak in panoramic views that stretch endlessly across the valley. The journey continues to Montepulciano, majestically perched on a ridge, where every corner reveals stunning vistas over the Val d’Orcia and Val di Chiana — a perfect picture of Tuscany’s beauty and history combined.
Tour Options
Itinerary
Meet our English speaking driver at your hotel on a comfortable Mercedes-Benz for start the journey to the beautiful Cortona: enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 600 meters (about 1968 feet) above sea level. This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno. The town has become very popular in the past decade thanks to the book by Frances Mayes, Under the Tuscan Sun (and the movie with Diane Lane) which is set in Cortona; the protagonist immediately falls in love with the town, its people, and the villa Bramasole that she purchases and fixes up. Time for relax or explore the area, the driver will suggest best things to do.
Leave at 11.30am for have a delicious light lunch at a family winery. Continue then to Montepulciano on a relaxing 30 minutes drive on the hills surrounded by breathtaking landscapes....of course your driver can stop the car anytime you want if you wish to take photos. Arrival to the charming Montepulciano around 2pm. This is a medieval hill town of rare beauty full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners.... Montepulciano has received great attention following the filming of the vampire saga Twilight sequel New Moon here and has seen a notable increase in visitors. A walk through Montepulciano is the best way to view the town and its beautiful landmarks as well as enjoy stunning views of the surrounding countryside covered by vineyards producing the famous Nobile which is possible to taste in the many wine shops located within the city walls.
Highlights
What's included
Pickup Locations & Times
HOTEL, APARTMENT, VILLA, IN FLORENCE. UPON REQUEST FROM DIFFERENT LOCATION
Traveller Ratings
Important Information
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Suitable for all physical fitness levels
- 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
Reviews(17)
Alex was extremely professional and helpful. He suggested sites and experiences to make our day extra special.
Thank you very much for taking the time to write your review. When our work is rewarded with positive comments like yours, it truly means a lot to us. Thanks again for choosing us, and we hope to see you back in Tuscany very soon!
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!!
Thank you so much for your kind words—it’s truly a pleasure to read reviews like yours, and they will certainly mean a lot to our team. We’re delighted that you enjoyed your experience with us and hope to welcome you back on one of our tours again soon!
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!
Hi, and thank you so much for your wonderful review! It truly means a lot to us to hear that our clients enjoy not only our drivers but also the experiences we organize throughout our beloved Tuscany. We put a lot of care into every detail, from the tours to the local insights, and it’s incredibly rewarding to know it makes a difference. Thank you again for your kind words, and we really hope to have the pleasure of welcoming you back!...
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.
Did you ever doubt our professionalism and skills? Just kidding… thank you so much for your kind words and for appreciating our Alex! We carefully select our drivers and, as you’ve seen, we always do our best to give guests the highest experience. Well, at this point there’s only one thing left—to welcome you back to Tuscany… and you already know who to call! Many thanks again for your wonderful review and your kindness in sharing it with others...!
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!
We couldn’t agree more with you—Cortona is an absolute gem! At the same time, there are so many other incredible attractions in Tuscany just waiting for you to discover them: charming medieval towns, rolling vineyards, breathtaking countryside, and of course plenty of good food and wine. So, the next time you decide to come back to Tuscany, make sure to get in touch with us and we’ll be delighted to organize everything for you. Thank you again for your wonderful review!
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!
Thanks a lot for the great review! We’re so happy you enjoyed Cortona, Montepulciano and, of course, our superstar driver. Now, don’t keep it a secret—spread the word! We’ll be waiting for you in Tuscany with more wine, views, and stories!
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.
It’s always such a joy to receive reviews like this — thank you so much for your kind words! We’re truly happy to hear that you appreciated our driver and had a great experience with us. Tuscany has so much to offer, and we’d love the opportunity to show you even more of its hidden gems and unforgettable landscapes on your next visit. So whenever you find yourself planning another trip to our beautiful region, don’t hesitate to reach out — we’ll be here and ready to help create more special memories for you.
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.
Hi Robyn, it's Massimo – your favorite driver (or at least I hope I am)! Thank you so much for your lovely review. It truly made my day. It was such a pleasure to share the wonders of Tuscany with you and to add a bit of my charm and humor to the journey. After all, what’s a tour without a few laughs, right? But let’s be honest, Tuscany has so much to offer that even a week wouldn’t be enough. There are still so many secret corners, stunning views, and mouthwatering dishes waiting for you! So here’s the deal: the next time you’re planning a trip this way, don’t just think about it – send me a message. I’ll be ready to dust off my hat (okay, I don’t really have one, but it sounds dramatic) and give you another unforgettable adventure. I might even throw in some new jokes – or recycle the old ones if they worked well enough! Until then, take care, and don’t forget: life is too short for bad wine, bad company, or bad drivers. Thankfully, I’ve got you covered on all fronts! See you soon (I hope)! 😊
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.
Hi Jason, Thanks a ton for your beautiful review! We’re thrilled that you enjoyed our driver, his top-notch professionalism, and the itinerary we cooked up for you—looks like we might just know what we’re doing after all! :) We can’t wait to have you back on board for another adventure. Max
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!
