Wine, Food and a Castle Tour in Monteriggioni and Siena, Tuscany, Italy

The Monte Chiaro shop and wine cellar in Monteriggioni

In which a chance invite in Brussels leads to a wine tasting in a medieval walled village, a guided tour of Siena, and one incredible meal.

We meet lots of interesting people in Brussels. With such a high percentage of expats and travellers at the various events we attend, we get plenty of casual invites to “look us up if you happen to be in the area.” So when we were invited to visit a winery, located in a Tuscan walled village, by the owner of the village castle – how could we say no?

It all started at a wine tasting. Our dear friends at Britxos invited us to sample wines by Italian producer, Monte Chiaro, with the head of the winery leading the tasting. While there, we started chatting with Carlo and Alessandro about the region, the difficulty working with tourism offices, website best practices and a whole host of topics we know a thing or two about.

We mentioned we were contemplating a trip to Spello and were encouraged to make the day-trip to Monteriggioni, just outside of Siena, for a private tasting and tour of the castle town. I’m not sure if they actually expected us to turn up, but a few months later I was emailing Carlo with our itinerary. True to his word, he arranged to meet us at the village gate.

These days Monteriggioni is a tiny walled town, populated by a handful of shops and restaurants. But, in its day, it was front-line defence for Siena from the rival Florentines. In fact, it was so important; the town was even mentioned in Dante’s Divine Comedy.

Picturesque Monteriggioni

The views from the castle walls are splendid – rolling hills and wineries, as far as the eye can see. From here, it’s easy to see why Monteriggioni was at strategic look-out point.

View from the Monteriggioni Castle walls

The stunning view of Monteriggioni from above

But we were here for the wine and Alessandro had just bustled into the Monte Chiaro shop and cellar on the village square. Alessandro’s ancestors bought Monteriggioni in 1720 and still own the castle (Haven’t you always wanted to own a castle?). Alessandro took over the family’s historic winemaking business in 2005 and hasn’t looked back since.

Inside the Monte Chiaro Shop – The family produces a variety of wines, as well as olive oil, honey and other local products.

The four of us descended into the cellar and our tasting began. Monte Chiaro offers a range of wines, from bright whites, to the richest of reds. They are all superb but, of course, we have our favourites. The 345 Chianti, the Brunello di Montalcino and the Primum Vinum, all found their way home with us. In fact, our taste in wines is shared by songstress, Joss Stone, who featured Primum Vinum in her recent music video for ‘The love we had.’

Our three favourite Monte Chiaro Wines – 345 Chianti, the Brunello di Montalcino and Primum Vinum

But even we can’t taste all those wines on an empty stomach, so when Carlo and Alessandro offered to take us for lunch at a truly rustic restaurant, we couldn’t refuse.

Osteria Tanaliberatutti is not a restaurant we would have wandered into on our own. In fact, it doesn’t really look like a restaurant at all. Stepping inside the tiny space, you’re welcomed by a deli counter stuffed with local meats.

Osteria Tanaliberatutti – Andrew is excited to try the local meats.

Duck around the corner however, and you’ll find yourself in a small dining room, where good things parade from the kitchen. We left the ordering up to our local experts and sat back to enjoy the ride: melt-in-the-mouth steak, chickpeas and spinach emerged on the table before us. (Not to mention a plate of the local charcuterie and cheeses and a healthy dose of the local wine.)

Good things happen when we let the locals do the ordering at Osteria Tanaliberatutti

After lunch, Carlo offered us an insider’s tour of UNESCO designated Siena, his hometown. Never ones to turn down local expertise, we bade Alessandro farewell, as he headed back to run the family business, (good wine waits for no one) and followed Carlo into Siena.

Stunning Siena, Italy

We strolled the narrow streets of this stunning Tuscan city, with Carlo pointing out the sights. Of course, ‘the sights’ for us included all of the best places to eat in town (mentally filed away until we can return.)

The beautiful streets of Siena, Tuscany

Despite the tourist crowds, we gaped in awe at the splendid Piazza del Campo, home of the Palio di Siena, a traditional medieval horse race run around the Piazza twice each year. It was impossible to imagine the breakneck speeds the horses and riders bolt around the circular piazza.

The UNESCO designated Piazza del Campo, home of the Palio di Siena

Before leaving town, we stopped to admire the Siena Cathedral, a stunning church built of multi-coloured marble. Carlo explained how an even larger addition was planned for the cathedral, but stopped due to lack of funds during the Black Plague. Construction never resumed as the plans were found to be structurally unsound, giving the exterior of the cathedral a rather lopsided feel.

The ornate Siena Cathedral

As we headed back towards our car, the skies finally opened; a good sign to start our trip back to Spello. We said good-bye to Carlo and contemplated chance meetings, the power of travel to bring people together, and good wine (but maybe that was because of the bottles clinking in our back seat.)

So, if by chance you ever meet us at an event, be careful about tossing invitations to travel to your hometown our way. We very well might take you up on them, especially if your family happens to own a castle or vineyard.

Love castles, palaces, and ruins like in this article? Us too! Don’t miss the full listing of Castles we’ve visited in Europe and beyond.  For more great restaurants around the world, check out our Restaurant Review page.