private tour

Private tour to Montalcino, Pienza and Montepulciano

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.



Explore 3 medieval Tuscan towns: Montalcino, Pienza and Montepulciano

Turn the postcard views into reality! A whole day to discover the stunning Tuscan countryside South of Siena. Dive into the picturesque landscape and beautiful medieval villages.


After passing Siena, continue through the ‘Crete Senesi’ beautiful area to reach the famous wine town Montalcino. The scenery is breathtaking here – cypress trees, fields and livestock with extraordinary combinations of green, grey and brown landscapes.

Brunello wine

The famous Brunello wine is produced here using the local Sangiovese grapes. Every activity in this town revolves around wine production and rightly so. Brunello is one of the finest and most prestigious wines produced in the whole world!

Inside Montalcino’s imposing fortress, visit ‘Enoteca La Fortezza’, a unique wine shop with a large variety of local Brunello wine.

Wander in Montalcino

Have a walk in the beautiful village, admire Piazza del Popolo, Palazzo dei Priori. Visit the churches of Sant’Agostino and Sant’Egidio and the beautiful Cathedral.


Stop in Pienza, a charming Tuscan town recognized by UNESCO as a worldwide cultural and natural patrimony site.

Birthplace of a pope

The history of Pienza is tied to that of Pope Pio II, born in Pienza on the 18th of October 1405 with the name of Enea Silvio Piccolomini. He was a great Humanist and wanted to transform his birth town from a small medieval hamlet into a Renaissance-style papal residence. Many of the palaces you see today in Pienza are from that time.

Walk in the Street of Love!

Get to the top of its hilltop location, admire the unforgettable view over the most picturesque valley, Val D’Orcia and the surrounding countryside. The streets in Pienza have curious names such as ‘Via dell’Amore‘, del Bacio, della Fortuna‘, (the Street of Love, of Kiss, of Luck!).

Artisan shops and pecorino cheese

Shop here, the streets are lined with small shops selling local crafts and regional specialties such as delicious ‘pecorino di Pienza’ wine and many shops are willing to give out some samples of their fare to taste.


Last stop of your Tuscan day: Montepulciano, located in one of the most breathtaking areas in Tuscany.

Culture and wine

This interesting wine town was entirely built on volcanic rock and stands about 600 meters above sea level. 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.

Discover Montepulciano

The town developed on a steep hill between the gates of Porta al Prato and Piazza Grande and is crisscrossed by short and narrow streets and alleys. There is plenty of sightseeing here and the Cathedral is worth a visit.

Don’t miss Palazzo Comunale, the temple of Madonna of San Biagio and the church dedicated to Saint Augustine.



A relaxing drive back to your accommodation in Florence concludes your private day in Montalcino, Pienza and Montepulciano.

…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 to Montalcino, Pienza & 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 on this tour to Montalcino, Pienza & Montepulciano?
It is totally up to you! Our vehicles have special permits/licenses to circulate almost everywhere (pedestrian areas included). As 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 in this tour, so you are free to decide the option that best suits your needs. The driver can suggest you according to your taste.



Are wine tastings included?
Wine tours/tastings are not included. If you are interested, 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.

Need Help or have a question?



There are no reviews yet.

Be the first to review “Private tour to Montalcino, Pienza and Montepulciano”

Your email address will not be published.

Swipe left for more reviews



Check Availability
and go to checkout


Pay with
your favourite gateway


Receive Booking confirmation

by email

Pay safe with

Send us your Quick Request

Lorem ipsum dolor sit amet, consectetur adipiscing elit. Ut elit tellus, luctus nec ullamcorper mattis, pulvinar dapibus leo.