private tour

Private tour to Montepulciano & Pienza

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.



Magnificent Tuscany – tour to Montepulciano & Pienza

Meet your driver at your accommodation in Florence and start diving through the stunning countryside of south Siena for a day of sightseeing. Discover ‘Crete Senesi’ beautiful area and the important medieval towns of Montepulciano and Pienza.

Stop in Montepulciano!

The scenery is breathtaking: cypress trees, fields and livestock with extraordinary combinations of green, grey and brown landscapes. Located in one of the most breathtaking areas in Tuscany, the unique wine town Montepulciano was entirely built on volcanic rock and stands about 600 meters above sea level.


Like many towns in Tuscany, also Montepulciano has Etruscan origins! Surrounded by walls and fortifications designed in 1500 by the Italian architect Antonio da Sangallo, by orders of Cosimo I de’ Medici.

Vino Nobile wine

Discover Montepulciano’s impressive Renaissance buildings, the beautiful churches and the ‘Vino Nobile’, one of the most distinguished Italian wine in the world. The town developed on a steep hill and is crisscrossed by short and narrow streets and alleys. Plenty of sightseeing here, the cathedral is well worth a visit!

Ancient palaces and churches

Visit Palazzo Comunale, the temple of the Madonna of San Biagio and the church dedicated to Saint Augustine. After admiring the sights of Montepulciano, ask recommendations to your driver for some great places to eat: try one of the local specialties accompanied by a glass of Vino Nobile di Montepulciano!

Don’t miss Pienza!

A short car ride for your next stop in Pienza, a charming Tuscan town recognized by UNESCO as a world-famous cultural and natural patrimony.

Pope Pio II’s birthplace

The history of Pienza is linked to Pope Pio II (original name Enea S.B. Piccolomini) born in Pienza the 18th of October 1405.

Great Humanist, he wanted to transform his birth town from a small medieval village into a Renaissance-style papal residence. Many of the palaces that you see today in Pienza are from that time.

Visit Piazza Pio II

Admire magnificent views over the surrounding countryside and Val d’Orcia from its hilltop location. The town’s main square was named after Pio II and is the center of the town. This trapezoid shaped piazza was filmed in ‘Romeo and Juliet’ by Franco Zeffirelli.

Explore the Duomo, Piccolomini Palace and the church dedicated to Saint Francis. The streets in Pienza have curious names such as ‘Via dell’Amore, del Bacio, della Fortuna’: Street of Love, of Kiss, of Luck!

Local shops and pecorino cheese

Have some shopping! The streets are lined with boutiques shops selling local crafts and regional specialties such as the delicious local cheese ‘pecorino di Pienza’, wine and many shops are willing to give out some samples of their fare to taste.

Hold this beauty

Arms laden with your purchases and your eyes filled with beauty, at the end of your tour to Montepulciano and Pienza from Florence, allow your driver to accompany you back to your car for the ride to your accommodation in Florence.

The landscape you can enjoy during your ride will remain with you for the rest of your life – the peaceful green hills, clay fields, vineyards and pastureland – all this is Tuscany.

…read more

Can we reserve a local guide directly on site, on the day?
Unfortunately, no! If you’d like to add this optional service you must book it at the time of reservation, or at least a few days in advance.



Is this tour, 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 on this tour to Montepulciano & Pienza?
It is totally up to you! Our vehicles have special permits/licenses to circulate almost everywhere (pedestrian areas included). Being a private service you are free to decide your own pace, with no rush.



Are the entrance fees included in the price?
The entrance fees are not included in the price. If you are interested, your driver can give you all the info to buy the admission tickets on site.

Keep in mind that normally in Italy, it is mandatory to have shoulders and knees covered to enter religious sites.



Are meals included?
Meals are not included on this tour. You are free to decide the option that best suits your needs. Your driver can suggest you according to your taste.



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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