private tour

Private tour to Montepulciano and Cortona

per party
All health and safety measures are in place. Also keep in mind that booking a private service you will be the only party in the vehicle. The top solution in terms of safety, comfort, privacy and flexibility. Relax and enjoy your experience.



Tuscan tour to Montepulciano and Cortona

Start your adventure from Florence through the stunning Tuscan countryside South of Siena. A splendid day of sightseeing to discover the charming Crete Senesi area, famous for its rolling hills with cypress trees, and the unique Montepulciano and Cortona towns.


The scenery is breathtaking – cypress trees, fields and livestock, with extraordinary combinations of green, grey and brown landscapes.

Built on volcanic rock

Like many towns in Tuscany, also Montepulciano has ancient Etruscan origins. Surrounded by walls and fortifications designed in 1500 by orders of Cosimo I dei Medici. Situated in one of the most beautiful areas of Tuscany, Montepulciano is a wine town entirely built on volcanic rock at about 600 meters above sea level.

Wine and history

Today Montepulciano is known for its very impressive Renaissance buildings, its beautiful churches and especially for its Vino Nobile (noble wine) one of the most distinguished Italian wines in the world.

The town developed on a steep hill between Porta al Prato and Piazza Grande and is crisscrossed by many short and narrow streets and alleys. There is plenty of sightseeing here and the cathedral is well worth a visit. Explore Palazzo Comunale, the temple of Madonna of San Biagio and the church of Saint Augustine.


Stop in beautiful Cortona, one of the oldest cities in Tuscany!

Ancient origins

Wonder in Cortona, one of the 12 great City-States of the Etruscan League. The Etruscan work is still visible in the foundations of Cortona’s massive stone walls. More than 2000 years of history make Cortona one of the most fascinating and characteristic Italian cities.

Wander in Cortona

Built on Monte Egidio above the Medici Fortress, Cortona has steep streets paved with huge stones. Almost the entire historic center of Cortona is Medieval or from the Renaissance.

Begin your visit in Cortona from the Medieval part, right from Palazzo Comunale located in Piazza della Repubblica. From here, a stairway leads to Piazza Signorelli where you can see Palazzo Casali where Etruscan Accademia is located.

From one of Cortona’s top walls, admire one of the most beautiful views in Italy – over the immense Val di Chiana, the mountains of Siena with the peak of Amiata Mountain and Trasimeno Lake.

The power and defeat

Cortona was a major seat of power during the Middle Ages. It held its autonomy against larger towns like Arezzo and Siena. The decline began at the beginning of the 15th century, when defeated by Naples and sold to Florence was no longer autonomous.

Not to miss in Cortona

In Cortona you will see the Etruscan Accademia museum, the Town Hall, Palazzo Laparelli, the Medici Fortress, the Cathedral, the Diocesan Museum, the Basilica of Santa Margherita, the churches of San Domenico and of San Francesco. A tiny town with so much to see! Enjoy your walk through ancient interesting and unforgettable places, churches and palazzi.


Ask your driver for suggestions for a great place to enjoy a typical Tuscan lunch paired with excellent local wines.



At the end of your private tour to Montepulciano and Cortona surrounded by the beauties of Tuscany, relax and enjoy a comfortable ride back to your accommodation in Florence.

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Is this tour to Cortona and Montepulciano accessible for people with disability?
Yes, it is! We can accommodate people with reduced mobility and foldable wheelchair/scooters users. Please note: it is mandatory to specify each specific need at the time of booking and in case of wheelchair/scooters, the exact dimensions to be sure they can fit in the trunk of the vehicle.



How much walking is involved in this tour to Cortona and Montepulciano?
It is totally up to you. Our vehicles have special permits/licenses to circulate almost everywhere (pedestrian areas included). Obviously, the best way to enjoy the visit of the historic city centers is by walking. Keep in mind that as a private service, you are free to decide your own pace with no rush.



Are meals included?
Meals are not included on this tour. Your driver can suggest you according to your tastes.



You may find additional info on our FAQs page, in the Private Tours section.

Free date changes

You can change your service date for free, as much as you want.

Credit for future tours

If you don’t know when you’ll be able to travel, you can convert your existing payments to credit, and use it whenever you want.

Gift or transfer

You can transfer your credit to a friend or family member, at no extra cost.

Free Cancellation

– Up to 24 hours in advance for Small Group Tours.
– Up to 72 hours in advance for for Private Tours & Transfers.

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