Brunello di Montalcino has a sort of ethereal charm that's got the wine world infatuated - think rolling hills in the soft Tuscan glow. Something about it being completely borne of the Tuscan terroir gives it a mystical quality through its embodying of a distinct sense of place - it's 100% Sangiovese, known locally in Montalcino as Brunello (hence the name Brunello of Montalcino), grown on the ancient marly soils that form Montalcino's hills, and subjected to the influence of the warm seas nearby. The Montalcino region lies within Siena, close to the center of Italy, and almost equidistant from Rome and Florence - and despite its vicinity to Tuscany and relatively much smaller size, its wines boasts such character (despite much lower natural yields) that it insists on being considered distinct and separate.

Sangiovese, otherwise known locally as Brunello.

For a wine to be considered Brunello di Montalcino, it must be exclusively Sangiovese as mentioned earlier, from the Montalcino area of course, and it must be grown to specific vineyard requires that dictate the altitude of its hillside locale, with the wines to be aged for at least 2 years in oak barrels and at least 4 months in bottle - it also can't be released for consumption before 1st January of the year following a 5-year term calculated from the harvest vintage. These are exacting requirements, and in fact, rather demanding ones that therefore imply that a whole lot goes into the wines before they ever reach your hands - but perhaps that's just as well what makes it so special and unique, commanding and deserving of its price tags.

Whilst precisely defined today, Brunello di Montalcino has its origins in the 1860's. Of course Brunello (that is Sangiovese) had been grown in the region for centuries up till that point, it wasn't until the 1860's that a clear and distinctive style had begun to crystallise, eventually gaining itself a serious following, and then finally hitting its apex in 1966 when it was finally granted DOCG status, thus enshrining the style. In those early days there were just a handful of producers who produced the style - just four in fact, with one of them becoming whom is known today as Castelgiocondo.

Castelgiocondo or Lovable Castle.

Castelgiocondo, so named after the village where it resides, was first built as a stronghold in the year 1100, so as to defend the road from the sea leading to Siena. It was here that a document was found that verified the tasting of a Sangiovese borne wine from the 1834 vintage from the estate, thus confirming the Castelgiocondo's place in Brunello di Montalcino history. The name Castelgiocondo itself is taken to mean "lovable castle", and given its historic nature, each expression from the estate features a fresco painted by Simone Martini, with the flagship Brunello di Montalcino depicting a documented attack on the Montemassi Castle in 1323. Whilst little documentation is available publicly on the ownership of the estate, we do know that closer to its recent history it was owned by a French group, and then subsequently an unnamed Milanese finance house. Yet what we do know is that Vittorio Frescobaldi, of the illustrious Frescobaldi family who today owns Castelgiocondo, had served as the manager of the estate throughout those phases of ownership, before eventually himself purchasing the estate in 1989. 

It might be worth noting that the Frescobaldi's have once stated that during the prior ownership by the French group, it was instructed that the estate should experiment with the planting of Sauvignon Blanc, Merlot and Cabernet Sauvignon, yet it was discovered that of the three international varieties, only Merlot worked well - in fact, it worked brilliantly. It was so impressive in fact that it had impressed the Mondavi family of Californian winemaking fame, who were at the time in discussions with the Frescobaldi's on a joint venture. Despite Robert Mondavi's keen interest in the Castelgiocondo estate, he nevertheless felt that it made no sense to create another Brunello brand, and thus the SuperTuscan Luce was born instead.

The Frescobaldi family's winemaking efforts are today led by Lamberto Frescobaldi.

Now by this point, we've mentioned the Frescobaldi family enough times that it warrants us properly introducing them. The Frescobaldi family is a prominent Florentine merchant family that traces its history back to at least the 13th century, having first found success through the export of Italian cloth, after which they began their expansion into banking, politics, you name it - along the way they've also birthed numerous literary figures, at least one of whom was good friends with the legendary Dante Alighieri. Now of course one of their most well-known work lies in being one of Italy's great wine producing families, with ownership of numerous well-regarded vineyards - one of which being Castelgiocondo, of course. The Frescobaldi's have been involved with wines for at least 30 generations, and today produce up to 7 million bottles of wines from Tuscany to Chianti, and across Montalcino through to Maremma. They even boast having supplied wines to the artist Michelangelo, as well as King Henry VIII.

The historic Castelgiocondo estate.

With that said, let's take a closer look at the hilly vineyards of Castelgiocondo. The Castelgiocondo vineyards are sizeably massive, numbering some 190 hectares. The vineyards in particular are in the southwest of Montalcino, and elevated at 300-400 metres in altitude. It features ideal conditions where it comes to soil drainage and sun exposure, with its soils characterised by galestro (clay-schist that's crumbly yet holds water), clay and ancient Pliocene sand, also being rich in calcium. It is here that the estate grows both traditional Brunello (Sangiovese) and also Merlot, and thus produces several grades of Brunello di Montalcino, as well as a Merlot expression named Lamaione.

Once harvested, the fruit goes through sorting, after which it is then fermented in temperature controlled stainless steel tanks, with frequent pump overs. The wines are then aged in wooden barrels, before further ageing in bottle as per Brunello di Montalcino tradition.

With all that said, thanks to the Sommelier Association of Singapore, we recently had the opportunity to try several of Castelgiocondo's wines at a tasting hosted by Wine Portal at Grand Cru Singapore!

Wine Review: Castelgiocondo Rosso di Montalcino “Campo Ai Sassi” 

Before we go right into Brunellos, let's warm up with the Rosso. 

Rosso di Montalcino is essentially the younger, more accessible counterpart to Brunello, also made from the same 100% Sangiovese grapes grown in Montalcino. However, Rosso is aged for a shorter period of time of just one year. It offers a fresher, more fruit-forward expression of Sangiovese wine. Producers also often use grapes from younger vines or barrels that don’t meet the strict standards for Brunello, making Rosso a more affordable way to enjoy the character of Montalcino without the wait.

This is the 2021 vintage of the Castelgiocondo Rosso di Montalcino “Campo Ai Sassi”.

Tasting Notes

Nose: Fresh and fruit-driven, with a trace of structure underneath. Opens bright and lively, with clear notes of cherries and raspberries at the forefront. There’s a floral lift of violets, a light mix of spices and a hint of vanilla. Minerality becomes more noticeable as it settles, alongside a subtle saline edge that balances out the fruits. 

Palate: Opens with juicy cherries and a vibrant acidity that gives it a real lift. Red fruits turn a little tart to sour strawberries and raspberry. Medium-bodied and quite approachable, it's got a texture that feels polished and not heavy. A light mineral character shows up as it moves through the mid-palate, along with a dusting of spice. There’s also a touch of sweetness on the fruit, which keeps it round and easy to drink.

Finish: On the shorter side. Lightly tart red fruits and a soft mineral note fade into the background.

My Thoughts

This drinks like a fresher, more accessible cousin of Brunello. It’s vibrant and berry-driven, with a lively tartness. While it’s enjoyable now, I could see this doing well with another 2–3 years of bottle age to round out the acidity and draw out a bit more complexity.

Wine Review: Castelgiocondo Brunello di Montalcino

Next up, we have the 2019 vintage of the flagship Castelgiocondo Brunello di Montalcino

Tasting Notes

Nose: Immediately more concentrated and layered compared to the Rosso. Rich vanilla and sweet oak form the base, but it's the deep potpourri notes, those dried rose petals and spiced herbs, that capture your imagination. There’s a quiet intensity here. Fruit is darker and more reserved, with everything wrapped in a warm, cedar-like richness.

Palate: The weight and structure is clear. There’s black cherry at the core, but it's surrounded by dried tobacco leaves, earthy minerality and a faint umami character of soy sauce. Tannins are present and firm, but they stay refined and never cross into leathery harshness. Bittersweet oak adds grip, and there's a fine layer of herbs and spices that lingers in the background with thyme, black tea, a little clove all unfolding slowly and deliberately.

Finish: Continues in that same layered, grounded tone. It trails off with dry slate, a hint of liquorice and those potpourri notes again, but now dried out and elegant. Minerality is more pronounced now at the end.

My Thoughts

Lovely depth and rich floral notes. But more importantly, this has mellowed beautifully in the bottle, with a softer acidity that makes the whole wine feel more settled and resolved. Compared to the Rosso, which is brighter, fresher and more tart-fruited, the Brunello feels like it’s moved into its second act of being deeper and more introspective. It’s less about exuberance and more about depth and patience. 

There’s a lot to unpack here, and it rewards the time you give it.

Wine Review: Castelgiocondo "Ripe al Convento" Brunello di Montalcino Riserva DOCG (2018)

The Ripe al Convento refers to a small Sangiovese vineyard perched on one of the highest hills of the estate which is located at a higher altitude of 450 metres, exposed to the afternoon sun and cold Mediterranean winds while growing on marly soil.

The wines of this vineyard are said to be more elegant, characterful and longer-lasting.

According to the technical sheet, the 2018 season was overall a good one thanks to cool and rainy winter which helped replenish water reserves in the soil, cool nights during summer which supported the development of colour and aromas, and sunny-windy conditions during the harvest period which helped preserve freshness and acidity while preventing disease. 

Tasting Notes

Nose: Deeply expressive, layered and floral. Rich dried florals and potpourri leap out first, along with a soft, perfumed intensity that pulls you in. Underneath that are waves of ripe plums, strawberries, vanilla and sweet oak, followed by cedar and cigar boxes. There’s a touch of rusticity of dry earth and forest floor—but it’s subtle, more of a grounding element in the background.

Palate: What stood out immediately was the texture and smoothness. This is a fairly dense wine, yet it's incredibly soft on entry, with a silky texture that carries weight without heaviness. Dark plums dominate the fruit profile, wrapped in warm spices—cassia, a touch of clove—and a very fine structure. The acidity is mild and integrated, not bright or punchy, and it allows the darker flavours to unfold more slowly. There’s liquorice, a faint herbal thread, and a cooling note of mint that shows up in the mid-palate. Tannins are ultra-fine, silky, and seamlessly integrated.

Finish: Moderately long. It pulls back into notes of dark roasted coffee, bitter chocolate and a gentle touch of vanilla. There’s a light, chalky minerality right at the back.

My Thoughts

This felt like the most complete and resolved wine of the range. The acidity has mellowed out beautifully, leaving behind a structure that’s rich but so smooth it’s almost deceptive. Everything feels well-aged and balanced. Compared to the earlier Brunello and the Rosso, this Riserva is initially more restrained and contemplative, but it instead rewards slow tasting and balance with even some minerality keeping it from feeling too plush or sweet.

This was easily my favourite of the Castelgiocondo lineup—texturally polished, aromatically complex, and just incredibly well-matured.

Wine Review: Castelgiocondo "Ripe al Convento" Brunello di Montalcino Riserva DOCG (2016)

After tasting the 2018 vintage, we're now on to the 2016 vintage of the same label. 

The 2016 vintage is described as challenging but ultimately one of the greatest in terms of grape quality due to a cold June that delayed flowering, but a warm summer with well-timed showers that allowed for full ripening of the grapes before a harvest season with plenty of sunlight, hot days and cool nights, and cool dry winds. These conditions aligned beautifully at the right moments to allow for ripe, healthy, fragrant and perfectly balanced grapes, ideal for age-worthy wines.

Tasting Notes

Nose: Ripe and layered, opening with a basket of black and red fruits; luscious blackberry and dried figs layered with tart morello cherry, then similarly a strong floral presence, mostly dried rose petals, alongside aromatic oak, cigar box, and old leather-bound books. As it opens, some black truffles sneak in to add a slightly earthy depth.

Palate: Silky, smooth and seamless in texture. Ripe black fruit dominates again with blackberry, morello cherry and figs, followed by deeper notes of leather and dried herbs. It’s rich and mouth-filling, with nearly all the acidity having mellowed out. The tannins remain rather firm, but they're very finely grained and never intrusive. There’s a slightly savoury undertone with leather, dried rose petals, a bit of incense and dusty cocoa, giving the wine a grounded complexity.

Finish: Long, lingering with light touches of leather, cocoa, a soft echo of savoury herbs and red fruit.

My Thoughts

This has clearly benefited from 2 additional years of bottle aging. Compared to the 2018, which showed more brightness and energy, the 2016 is more settled, with the acidity almost completely rounded off.

It’s already ready to drink, but it’s the kind of wine that will keep developing, likely picking up yet more dried fruit, leather and gamey character over the next decade. The balance is already there, and it's really gently persistent and well-structured.

@CharsiuCharlie