I have spent most of my time here, wandering these old streets, learning about the wine and exploring the countryside down below. It’s a marvelous old city, full of interesting sights and those views, wow I just can’t get enough. Here are 5 free things to do in Montepulciano Italy that I don’t want you to miss on your next visit.

Etruscan Tomb at Cantina Casanova
The Etruscans were a civilization that resided in Italy and the region before the Romans. In fact, it’s where the name Tuscany originates from. They dominated from the 10th century BC to the 1st C BC. The Etruscans had city-states, extraordinary places that were obliterated by the Romans when they conquered the area.



What we know of them mostly comes from their tombs and Montepulciano is full of them. One that you can visit for free is at Podere Casanova wine room on the main street. At the rear of the cellar is a tunnel descending into the stone. The kind gentleman that runs the room will take you down and explain to you what you are seeing. It’s a wonderful way to whet your appetite to all things Etruscan. There are many other tombs all privately owned and most inaccessible for safety reasons.
Sanctuary of San Biagio
Located down the steep cliff from the medieval city lies this church. Built in 1520, it is a beautiful example of renaissance architecture. You may have already noticed it from above, as it adds such a picturesque component to the views of the valley.



The sanctuary is built in the shape of a Greek cross and the interior is very simple and elegant. The day I entered, a wedding was being prepared for, the flowers such a pretty addition. The exterior is stunning with the warm limestone contrasting to the bright green grass. The bell tower is nestled right up against the church, a unique feature. I’m not sure how, but if you told me this was constructed a few years ago, I would believe you, it’s that pristine.
Country Roads
While you are at the sanctuary, keep going. On one side down a tree lined avenue, find the local cemetery. It’s a lovely respite and the road from there continues on back up to the old city. Take the smaller country roads in the opposite direction and now you are going to experience rural Tuscany.


And the atmosphere here is surreal. On a foggy day the air is filled with millions of diamonds reflecting in the Tuscan sunshine.



On a clear day, see the vineyards that are producing the grapes for that special wine, Vino Nobile di Montepulciano.


Don’t forget to keep glancing up to your right, for views of the soaring medieval city above. The farms and country folk are as friendly as can be and there is surprisingly little vehicular traffic to contend with on these small roads.
Fortress & Municipal Gardens
Back up in the old city, we are walking to the upper echelons at one end. Here we find the Giardino Montepulciano and the Fortezza Medicea. This old fortress was first constructed in 1261. Over the centuries it has been rebuilt many times after being destroyed because of conflict between Siena and Florence.



What is left of it today, is home to the consortium that regulates the DOCG wine produced in this region. The stunning little Italian garden that sits just outside the fortress is an oasis. Complete with a small shrubbery maze, the views beyond that far wall are simply breathtaking.


The sculptural exhibits, old wells, decorations and other features make this the perfect spot for a rest, romantic stroll, or to bring a little picnic.
Thursday Market
Always on the lookout for a market, don’t worry I have you covered in Montepulciano. Every Thursday head down to the bus station. The large lot beside will be set up with the travelling vendors. This is where you will find the locals shopping as it is full of seasonal produce, fresh from the fields.



There are food trucks selling savory porchetta and rotisserie chickens as well as cured meats and cheeses. See everything from fresh flowers, clothing and even live chickens and pigeons, regular items on some menus here.



There are other places I could point out, like the numerous 2,500-year-old sarcophagi that decorate the exterior wall of the Palazzo Bucelli or the quirky and expensive boutique stores perfect for window shopping. But I will leave those and more for you to discover on your walking adventures around enchanting Montepulciano.