After spending a day revelling in the extraordinary sights of the Tuscan town of Siena, we drove out into the Tuscan hills towards the Chianti wine region. I must admit I didn’t really know much about this region, apart from what I’d seen in a movie called “Under The Tuscan Sun”. I knew the region was famous for growing grapes and olives, but had no idea that it was brimming with medieval Tuscan villages you must see.

We were booked into a hotel in a hilltop medieval village called Castellini in Chianti, and upon arrival we were completely blown away. The Hotel Palazzo Squarcialupi (don’t ask me to pronounce it!), on the main street of Castellina in Chianti, was a vision of 15th century Renainssance architecture overlooking beautiful gardens and vineyards in the valley below.

Views from our hotel suite in Castellini in Chianti

We discovered that we had been upgraded to a suite, featuring a separate living area and spacious bedroom in a loft above. Our own private little balcony overlooked the Tuscan countryside, worthy of an exclusive resort. We were in heaven!

The Pool and Gardens at our Hotel in Castellini in Chianti

Not only this, but it also had its own Day Spa – La Tinaia Wellness Centre, located in the basement of the hotel, with sauna, steam room, jacuzzi and changerooms equipped with everything you need. It was the ideal place to relax after a long day of driving and poking around the numerous medieval Tuscan villages we visited.

The Spa in the Basement of our Hotel

Castellini in Chianti

This charming Tuscan village, dating back to the fifth century B.C., located between Florence and Siena, was fortified by hexagonal walls that still stand today. Castellini in Chianti, whose emblem is the black rooster, main street of Via Ferruccio is dotted with little cafes, restaurants, wine cellars and souvenir shops.

The main street of Castellini in Chianti

As we strolled down the main street we noticed a few of the significant historical buildings, including our hotel – formerly the Palazzo Ugalini, Palazzo Bianciardi, The Church of the S.S. Salvatore, Piazza del Comune and the Medieval Castle.

Medieval Castle in Castellini

For a fascinating look into Castellini’s history you can visit The Archeological Museum of the Chianti Senese that is located in the main piazza.

S.S. Salvatore Church in Castellini in Chianti

Ristorante in Castellini

Each time we walked around the village during our four day stay, we noticed something new. On the main thoroughfare, via Chiantigiana, we came across the statue of the Black Rooster and a shop selling cycling jerseys from the Chianti Classico bike ride. We also came across a Winery, where you could partake in wine tasting and select from a vast array of local wines. We immediately thought, “why not”?

The Black Rooster – Emblem of Chianti

Castellini in Chianta streets

Possibly one of the highlights of our stay was an evening wine tasting and dinner tour to two local vineyards. We jumped aboard our mini bus with our guide and driver and wound our way around the narrow dirt roads of Chianti seeking out two particular wineries.

Vineyard in Chianti

On arrival we were shown around the vineyards, that had been owned by the same family for centuries and afterwards got to taste their wines.

Wine Tasting in Chianti Winery

The family then served us a delicious traditional 4 course meal with wines to match each course. Along with cheese, olives and prosciutto, we were treated to the local dish of pappa al pomodoro, a Tuscan vegetable bread soup.

A delicious dinner at a Winery in Chianti

Radda in Chianti

On our first day of touring Tuscany, after consulting the local Tourist Information Office, we set off into the Chianti countryside with a map and a recommended itinerary for our day’s driving. A short distance away, rambling through the undulating countryside, we came to Radda.

Some of the countryside on our drive to Radda in Chianti

We had a stroll around the town and into the small park where there was a fruit and vegetable stall setup doing a roaring trade. We purchased a couple of sweet peaches to eat for our morning tea.

Glorious Gardens and Fountain in Radda

A Fountain in Radda

San Stefano Church in Radda

We came to the municipal building or Palazzo del Podestà, which was extended several times over the past couple of centuries to include jail cells.

Palazzo del Podestà in Radda

Radda Castle

Vertine

Our drive continued to the small pretty hamlet, or castle of Vertine, that is surrounded by vineyards and olive groves. Vertine is located near Gaiole in Chianti.

Vertine Castle

The very well preserved Vertine with its original medieval appearnace is enclosed within massive walls. Inside the walls sits the quaint Church of San Bartolomeo a Vertine featuring renaissance frescoes on the interior.

Inside the Walls of Vertine Castle

Small Church in Vertine

What I liked about this 11th century castle is that it is still inhabited with residents that actually live inside the castle. There are no shops or other tourist attractions except one cafè serving coffee and fresh cakes.

Vertine Castle

Volpaia

We moved onto the small fortified village, referred to as a “castello” in Italian – Castello di Volpaia, which entailed a drive up an unsealed narrow road, not far from Radda in Chianti.

Bell Tower in Volpaia

Volpaia retains a great deal of its original architecture and has been attractively restored. Although more tourist-driven, we found this village to be charming.

Volpaia Castle

There are three excellent restaurants in this village with amazing panoramic views over the surrounding vineyards and forests, so it was the ideal place to stop for a bite of lunch and a glass of pinot grigio.

Ristorante in Volpaia

The winery that produces the wine Chianti Classico operates within the walls and you are able purchase the wine at the cellar door.

Small quaint church in Volpaia

Montefioralle

We wound our way up to another fortified village, just a few kilometres from Greve in Chianti, called Montefioralle. It’s probably one of the most ancient in Chianti and is still today enclosed within its original walls. Apparently during the Middle Ages it was one of the largest military and administrative centres of the area.

The Village of Montefioralle

The ancient passageways, formerly the entrances to the castle, and the fact that is is virtually free of traffic, makes it an ideal village to explore by foot.

The narrow lanes of Montefioralle

A shop in Montefioralle

Vineyards stretch away in every direction round about the village that makes it perfectly picturesque.

The countryside surrounding Montefioralle

The principal historic monument in Montefioralle is the Church of San Stefano, which is at roughly the highest point in the village.

We also noticed that there was a small cottage offering Italian cooking classes, just outside the village walls, which was very tempting if time had permitted.

A Cottage offering Cooking Classes in Montefioralle

Barberino Val d’Elsa

On the following day we headed off in the other direction, on the western side of Chianti, towards the village of Barberino Val d’Elsa. The town has a long spindle-like shape, where the main road runs down the centre connecting the two main gates of the old town: Sienese and Florentine Gates.

Gate into the village of Barberino Val d’Elsa

Barberino Val d’Elsa street

Entering the Sienese Gate we encountered century’s old buildings with beautiful wooden doors and clean stone walls. Halfway down the street, is the Palazzo Pretorio and then further along the rear of the San Bartholomew church, and the Pilgram’s Hospital.

The main street of Barberino Val d’Elsa

Walking around to the main thoroughfare, we came to the front of San Bartholomew Church and admired the terrace in front of this neo-gothic style church. We found it to be a beautiful spot to admire the soft hills and the patchwork of olive groves, vineyards and small forest alcoves, surrounding the town.

San Bartholomew Church in Barberino Val d’Elsa

San Gimignano

We were on a mission this day to visit the medieval town we had heard so much about. San Gimignano, a small walled village perched high on a hill about halfway between Florence and Siena, did not disappoint.

Gate into San Gimignano

Although the most touristy and busiest of the Tuscan medieval villages, we were fascinated by its medieval architecture and towers that rise above all the other buildings.

The Walls of San Gimignano

The hill has been inhabited since the Etruscan and Hellenistic period, probably due to is dominant position that allowed a careful watch of the rich Elsa Valley below. The striking fourteen towers of San Gimignano of various heights, which have withstood wars and time continue to define the city making its unique skyline its international symbol.

One of the 14 towers in San Gimignano

San Gimignano Museum

A stroll through the core of San Gimignano, in the shadows of its surviving towers, is simply delightful. At the centre of the town is Piazza della Cisterna, named for the cistern that is served by the old well standing in the middle of this square. However, we found this square to be inundated with day trippers and quickly moved to the outskirts of the village and traced around the ancient town walls.

The main square in San Gimignano

Nearby on Piazza del Duomo stands the town’s Romanesque cathedral. Also called the Collegiata di San Gimignano, the interior is the big drawcard. Inside the cathedral is extensively frescoed, dating back to the 1300s. The colours you see are the original ones painted and their vividness and brightness is awe-inspiring.

Church Collegiata di San Gimignano

I must confess that the shops along the narrow streets, just after you enter through the main gate into the walled town are stupendous. My husband and I both purchased handmade leather bags, belts and shoes from a local shop. There was also beautiful linen items, such as tea towels, bread baskets, tablecloths, placemats and napkins.

Ristorante in San Gimignano

After we walked and shopped, we were hungry and ready for some sustenance. Strangely enough we found this amazing cafe/bakery with Italian sweet treats that you would need to see to believe!

An enchanting archway in San Gimignano

Apart from grape growing, the area is well-known for producing some of the best saffron in Italy; you’ll find the spice for sale in shops and as a flavouring in meals at some of the finer restaurants.

Views from San Gimignano hilltop

Monteriggioni

After we spent a good part of the day hanging around San Gimignano, we consulted the map the young lass at the Travel Information Centre marked for us, and set off for the castle of Monteriggioni, near Poggibonsi. As with all of the Tuscan castles we had visited thus far, this one was perched high on a hilltop overlooking vineyards and olive groves in the province of Siena.

The Castle of Monteriggioni

We discovered that this particular castle represents one of the most important walled castles in the territory. Monteriggioni is incredibly well-preserved with an intact structure as if time had stood still. Its strategic position on a hilltop spectacularly dominates the surrounding landscape.

Stairs up to Monteriggioni Castle

The castle was built by the Sienese between 1213 and 1219 for defensive purposes to be on the lookout for any armies approaching Siena. It impressively boasts 14 towers along which the guards used to walk and patrol the walls. There are also two gates, one called the Franca or Romea Gate  and the other known as the Florentine Gate.

Romea Gate at Monteriggioni

A few steps inside the gate and you’re already in the heart of the village in the main Piazza di Roma onto which the Church of Santa Maria Assunta faces.

Church of Santa Maria Assunta  in Monteriggioni

The rest of the square is lined with shops, cafes and restaurants. Monteriggioni really has a strong medieval feel about it, as evidenced in mannequins dressed up as knights and shops that sell medieval artefacts.

Ristorante in the Piazza of Monteriggioni

Every July within the fortified walls of the town a special event is celebrated: the Medieval Festival of Monteriggioni, one of the best medieval festivals in the region.

A quaint shop in Monteriggioni

Our four days in Tuscany flew by very quickly and we were understandably reluctant to leave this beautiful region, as we felt there was so much more to discover here. Each Tuscan village we visited was unique and had its own vibe. We could have easily lost ourselves here for a few more days under the Tuscan sun in a wine drunk haze!

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