Despite being established after Sassicaia (in 1977) Grattamacco is a pioneer in its own right. Besides planting Bordeaux varieties, Piermario Meletti Cavallari retained some Sangiovese, uncommon in general Bolgheri identity. The estate was the first to bottle a Bolgheri Rosso in 1994, writ large on the label to introduce world to the area. He introduced Vermentino to the region shortly after. Partly fermented and aged in wood, it is still one of the estate’s gems. Grattamacco was also the first certified organic estate in zone – as of 1997.

It was purchased by Claudio Tipa in 2002 (his second estate after ColleMassari in Montecucco, with Poggio di Sotto in Montalcino added afterwards). Along with his winemaker, Luca Marrone, they continued the innovative spirit, planting bush vines – or alberelli to respond to hot, arid conditions. Other estates have since followed suit. The IGT L’Alberello bottling is a unique field blend, co-ferment of Cabernet Sauvignon and Franc.

In the winery, Marrone relies more on intuition than technology. His wines are structured though fine rather than muscular, and judiciously oaked. Chalky, textured, salty-edged and full of Mediterranean herbs, they speak eloquently of place.

One of Bolgheri’s original pioneers, Eugenio Campolmi purchased a property next to Ornellaia in 1983 planting 4 hectares to start. He and his wife, Cinzia Merli launched their first wine, Paleo, in 1989. Originally a Cabernet Sauvignon and Sangiovese blend, it morphed into a 100% Cabernet Franc by 2001 – the region’s first ever.

A year later, Campolmi passed away at the age of 40. Since then, Merli has carried on their vision with grace and determination. Besides the help of consultant and friend Luca d’Attoma, she is now joined by her sons Elia - vineyard manager - and Mattia, responsible for marketing and sales.

The estate is also known for IGT bottlings Scrio (Syrah) and Messorio (Merlot). The only Bolgheri DOC wine produced represents the classic Bordeaux blend of the denomination (with a dollop of Syrah).

As Le Macchiole adds to its holdings (now 35 hectares), the focus is in the vineyard. Cultivation is organic with a concerted effort to lower copper and sulphur by using alternative products like algae. They are increasing the amount of head-trained alberello vines, leaving more fruit on the plants and picking earlier. In the winery, extractions are gentler and the IGT reds are vinified in cement. The wines see less new wood at lower toast levels and a portion is aged in amphora. The results are palpable in the freshness, fruit purity and balance.

Finally, there is also an attention to more sustainable packaging including lightweight bottles (380 grams) and recycled cardboard.

Surely the jewel – or jewels – in Frescobaldi’s crown, the adjoining properties of Ornellaia and Masseto stand apart from the rest of the family’s stable. Established by Lodovico Antinori in 1981, Ornellaia made its way into Frescobaldi’s hands by way of Mondavi after Lodovico sold it to the latter in 2002.

While Masseto was originally released as a second wine to Ornellaia with the 1986 vintage, the two have since been divided into two estates. The vineyards are clearly separated by a stone wall and have their own winemaking facilities and teams. Nonetheless, both are overseen by one technical director. After almost 18 years at the helm, Axel Heinz passed the reins to Marco Balsimelli in 2023. The Tuscan-born Balsimelli brings over 15 years of experience in Bordeaux having worked with renowned consultant Eric Boissenot.

A complex mix of sand, marl and limestone pebbles, Ornellaia’s vineyards favour the Cabernets. The flagship wine is Bordeaux in blend with a Mediterranean temperament. Recent vintages have seen as little as 55% Cabernet Sauvignon, though Balsimelli is working to restore it to its original 80-85% - with Lamberto Frescobaldi’s blessing. Of note as well is the Bolgheri Bianco: a harmoniously oaked, creamy and complex 100% Sauvignon Blanc (which will soon incorporate a dollop of Semillon).

As for Masseto, it sits on an upper plateau distinguished by its cool, blue clay soil rich in marine fossils. Originally conceived as a 100% Merlot, it now includes a small percentage of Cabernet Franc in certain vintages. Silky and seductive, this seminal Italian Merlot has reached a fascinating level of understated opulence. It is also among Italy's most stratospherically priced.

Inextricable from the evolution of Italian wine, the legend of Sassicaia has been relentlessly recounted. Born as a Vino da Tavola, this Cabernet Sauvignon-dominant vanguard of the Super Tuscan movement eventually helped spawn the IGT classification and provided the model on which fine Bolgheri reds were fashioned.

Created by Mario Incisa della Rocchetta and honed with the help of Giacomo Tachis, Sassicaia’s renown and production grew under Mario’s son Nicolò. Today, the latter’s daughter Priscilla assumes the role of Brand Ambassador for Tenuta San Guido. Despite such noble legacy, she remains refreshingly humble. Equally forthright is CEO Carlo Paoli who took over from Tachis in 2009.

The estate doesn’t cultivate a sense of inaccessibility, nor should its other two labels be considered second or third wines as in the Bordeaux model. Nicolò launched the Merlot-led Guidalberto in 2000. It hails from specific plots of clay with stone – rather than sand. One-quarter of the price of Sassicaia, it is meant to be more approachable and expressive in youth but still age worthy.

Le Difese is San Guido’s entry point. Blending estate-grown Cabernet Sauvignon with Sangiovese purchased from two families in Rufino and Montespertoli, it represents a panorama of Tuscany.

As for Sassicaia, it is still among Italy’s most expensive, sought-after wines, even at its current average production of approximately 200,000 bottles per year. Older celebrated vintages like 1972, 1985 and 1988 are true unicorns. But for all its fanfare, Sassicaia is not a wine that wows immediately. Instead, it woos gradually.

With just 0.5ha vines, Rita Tua and Virgilio Bisti started making wine as a hobby in 1984. Their Bordeaux blend, Giusto di Notri was immediate appreciated. But it was the 2000 vintage of Redigaffi that earned them a home run. Besides joining the ranks of Italy’s top Merlot, it put Suvereto on the map.

The estate has grown to over 60 hectares with 12 labels accounting for upwards of 300,000 bottles. Vineyards for the top wines are still around the original farmhouse. High density plantings (5000-9000 vines per ha) expand over the gentle slopes. The soil is rich in schist. Where clay prevails, Merlot is favoured.

Today, Rita’s daughter Simena and son-in-law Stefano Frascolla manage the company. Their son Giovanni who studied oenology has recently joined the refreshingly-young winemaking team though consultant Luca d’Attoma continues to give his guidance.

The style has long been ultra-concentrated, opulent and generously oaked, particularly at the top tier. However, recent vintages demonstrate a bit more focus on fruit purity. The amphora-fermented Keir offers an exciting contemporary expression of Syrah.

Most recently, the family has been investing in Cabernet Franc, planting at a cool northeastern exposure. Watch this space.

Owned by the Contini Bonacossi family since 1926, the Capezzana estate and Carmignano DOC are virtually synonymous – though the former predates the latter by over 1100 years. After bringing back cuttings from Château Lafite, Ugo Contini Bonacossi was instrumental in establishing the denomination in 1975 with mandatory inclusion of Cabernet (Sauvignon and/or Franc).

His daughter Bernadetta has been winemaker since 1998, and her 36-year-old son Hector is poised to take over when she retires. There is continual evolution here. The Barco Reale now sees shorter macerations and partial refinement in stainless steel for a fresher, more immediately drinkable wine than past versions. As for the Carmignano, it has transitioned away from barriques to ageing in a combination of tonneaux and larger oak casks. The estate boasts a library going back 100 years of this incredibly ageworthy archetype.

For Benedetta, Vin Santo is like a second child, and Capezzana’s is among the most exemplary of its category. Also not to be missed is the IGT Toscano Bianco - an oak and acacia aged Trebbiano Rosa - and the estate’s olive oil.

At cool, stony heights in the subdistrict of Gaiole, Castello di Ama did much to raise the image of Chianti Classico at a time when the region was underperforming. Today, it retains its status as one of the top players of this now dynamic denomination.

Daughter of one of the four founders, Lorenza Sebasti is the current CEO. Marco Pallanti has been the winemaker since 1982. Their 20-something-year-old son Arturo officially joined them in 2021. Despite having studied oenology, he confessions an enthusiasm for management and has assumed responsibility with confidence and ease.

The leitmotif of the range is polish and sophistication. The estate’s annata Chianti Classico was born in 2010 after extensive replanting in the 1990s. It is made from younger, more productive plants while San Lorenzo hails from older vines. The latter is one of the best quality/price ratio Gran Selezione of the entire zone.

Alas, after long championing this new category, Castello di Ama is one of the few estates to lose out with the recent changes to the discipline. As international varieties will soon be prohibited for Gran Selezione, San Lorenzo will no longer be blended with Merlot. Conversely, La Casuccia will be declassified to IGT as of the 2022 vintage to retain its identity. As for Bellavista, which was among Chianti Classico’s earliest single vineyard bottlings in 1978, it will see a reduction of Malvasia Nera to conform to the stricter 90% Sangiovese minimum.

DOCG drama aside, one of the other not-to-be-missed gems is L’Apparita. Tuscany’s first commercially-produced 100% Merlot in 1985, it allies the soft, supple curves, intrinsic to variety, with unmistakable flavours of place.

A visit here usually starts with the elegant Laura Bianchi trotting to Il Poggio. From this hallowed knoll, a 360-degree view reveals much of the estate’s 70-plus hectares of vineyards (and 225 of forest). To the west, the towers of San Gimignano are visible. This is where Laura’s grandfather was from. He went to Milan to work in the textile industry and made enough money to buy the Monsanto property in 1961.

Laura’s father Fabrizio joined shortly after, and in 1968 bottled Il Poggio separately. Now a Gran Selezione, it was Chianti Classico’s first single vineyard bottling. Recently, it has been discovered that the site is on a rare outcropping of Pietraforte – calcareous sandstone, which may explain the finesse and longevity of this wine.

The tour continues with a walk through the 300-metre-long underground tunnel which leads to a precious archive of older vintages. Continuing the tradition started by her father, Laura keeps aside 2000 bottles of Il Poggio each year to release at least a decade later.

While Il Poggio may be the estate’s flagship, the Riserva is its bread and butter. Inverting Chianti Classico’s pyramid, it is produced at a 4 to 1 ratio with the annata bottling. For over 70 years, it has been crafted to offer accessibility in its youth as well as serious cellaring potential.

Castello di Monsanto’s legacy appears set to continue for decades as Laura’s 30-something year old daughter Giulia Cecchi is following closely in her footsteps.

Greek-born Princess Coralia Pignatelli della Leonessa is a true force of nature. She and her husband Riccardo arrived in Chianti Classico in the 60s purchasing a medieval hamlet in the Castelnuovo Berardenga district. She made her first wine in 1971 but continued selling most of the grapes, then wine in bulk until she was suddenly widowed in 1985.

Instead of abandoning the property she doubled down, gleaning knowledge from renowned consultants such as Giacomo Tachis. Today she continues working with Federico Starderini (think Poggio di Sotto). Nonetheless, there is no doubt who has the final say.

Coralia prizes body and power. Her wines are vertical and steely. She is never in a rush to put them on the market. They typically need years in the cellar and lots of oxygen to open. Even the Chianti Classico which hails from lower plots on marine sand can be squirreled away. The Riserva is crafted from higher elevations, where Alberese (limestone-rich marls) prevail. It is one of the denomination’s most cellar worthy gems.

Now well into her 80s, Coralia still insists on blending the wines. Obviously, there is concern about the fate of this venerated estate. The recent presence of her son Luigi has dispelled some of the speculation.

For being an ‘outsider’, Piemontese-born Paolo De Marchi is one of Chianti Classico’s most beloved personalities.

He was just 5 years old when his parents purchased the neighbouring hamlets of Isole and Olena in the western side of the zone merging them into a single estate. It took years and significant investment to achieve the renown it enjoys today. Much of this is a credit to De Marchi who started in 1976 after completing his studies viticulture and winemaking.

He is considered a Sangiovese advocate due to his iconic barrique-aged IGT bottling Cepparello. However, the estate’s pillar wine – the annata Chianti Classico - always hovered around the denomination’s 80% minimum. De Marchi sought complexity by including Canaiolo Nero and Syrah, and believes that blending will be a useful tool to mitigate the effects of climate change.

Among his many contributions to the region, De Marche’s massal selections gave birth to specific Sangiovese clones now widely used. The estate became a magnet and incubator of talent, giving credibility to those who worked there.

It also caught the attention of Christopher Descours’ EPI group (which owns Biondi-Santi). After the French investment firm purchased Isole e Olena in June 2022, De Marchi stayed on until 2023 when he returned to his Sperino estate in Piedmont. Emanuele Reolon has assumed the role of Technical Director.

Besides a noticeable redesign of label, the new ownership has continued the work De Marchi started on a new cellar and extensive replanting is underway. They have phased out Syrah from the Chianti Classico and are also increasing the percentage of larger casks for ageing of Cepparello.

It is too early to evaluate the impact on the wines. Despite De Marchi’s departure, his spirit is, for now, still inextricably woven into Isole e Olena’s fabric.

Twenty-six generations (and counting) with 26 wineries around the globe, the Antinori clan has made an undeniable impact on Italian wine raising both the quality and its renown worldwide. Much of the growth and progress is thanks to Florentine nobleman Marchese Piero Antinori. He led the company from 1966 through some of its most difficult times and the general nadir of Italian winemaking. Today, his three daughters Alessia, Allegra and Albiera are at the helm - the latter now president.

Headquarters are in the Chianti Classico zone, though for long, more emphasis was placed on the Super Tuscans made there. Opposite sides of the same coin, Tignanello and Solaia are respectively Sangiovese and Cabernet Sauvignon dominant. The family’s expansion in Tuscany includes Guado al Tasso in Bolgheri, Pian delle Vigne in Montalcino and La Braccesca in Montepulciano.

In the last decade or so, Antinori has made considerable investment in Chianti Classico signaling a rekindled conviction in the denomination. Significantly, the launch of three new Gran Selezione brings the grand total to four which represent the UGAs of San Donato in Poggio, San Casciano, Castellina and Gaiole. These are among the most the exciting wines the estate has put out.

While each property has its own dedicated winemaker, Renzo Cotarella is the longstanding technical director of all the estates. The objective is to keep style consistent, yet the identities separate.

One of Tuscany’s most prominent noble families and among Italy’s strongest wine brands, Frescobaldi delivers the gamut from volume-driven to iconic labels. Thirtieth generation, UC Davis-trained Lamberto Frescobaldi has led the company since 2013, overseeing more than eight estates.

It is difficult to choose just one that represents Frescobaldi. Among the most historic, Nipozzano is a reference in Chianti Rùfina. The family now boasts properties in all three major Sangiovese DOCGs with recent purchases of Tenuta Perano for Chianti Classico and Calimaia for Vino Nobile joining Castelgiocondo for Brunello. The latter’s sister estate of Luce featuring a Sangiovese/Merlot blend drew attention for its initial collaboration with Mondavi. Kept under a separate umbrella, the Bolgheri properties of Ornellaia and Masseto are surely Frescobaldi’s superstar Super Tuscans.

The leitmotif across the range is clean, polished, modern wines. Oak is much better managed than in the past but still makes itself known in some of the wines.

Perhaps the most unique of all Frescobaldi’s offerings is the collaboration with the Gorgona Penal Institute. This island off the Tuscan coast is reserved for convicts completing their sentences. They work in the vineyard and cellar to hone skills that will help them find work as they transition back into society. A textural and savoury blend of Vermentino and Ansonica, the white is particularly worth seeking out.

Translating as ‘hill of birds’ nests’, Montenidoli has served as a nurturing environment since Elisabetta Fagiuoli and Sergio Muratori acquired the abandoned property in 1965. The couple moved from Genoa to helped troubled children – not produce wine.

Fagiuoli took to restoring the neglected vines which had been planted after the second world war. Her first vintage was 1971. She sought the advice of experts but has always done things her way.

Like many of her peers, Fagiuoli makes three Vernaccia di San Gimignano. What stands out at Montenidoli though, is that the distinction between each is truly defined. Fiore is a beautifully transparent ‘naked’ expression made from free run juice with refinement on the lees in stainless steel. Tradizionale is a more rustic version that references the past with skin contact and ageing concrete vats. Finally, Carato is fermented and aged in barriques – mostly used. It is a sumptuous tip of the hat to Burgundy.

The Sangiovese-based reds are also worth seeking out and in fact were made long before whites were introduced in 1984. The Triassico label from a 2ha plot of bush vines on iron rich soil is bottled in magnum only. Proceeds go to a special foundation set up when Muratori died in 2012 which houses seniors together with youth in rural surroundings for the mutual benefit of both.

Behind her disarming smile, Fagiuoli is a force. Pushing 90, she is also as sharp as a tack. Until 2024, she continued to be involved in winemaking and in 2025, was spied directing reception of the harvested grapes.

Montevertine has never been tempted by the trappings of international varieties or the muscular extracted style that became popular in the 90s.

Sergio Manetti had great foresight to buy in the cool, forested heights of Radda in 1967. From 2ha planted in 1968, the estate now comprises over 17ha across 9 vineyards. Manetti’s son Martino continues to craft just 3 wines with well-defined identities.

The first wine, Montevertine was launched in 1971 with immediate success. It was bottled as a Chianti Classico until Sergio renounced the denomination in 1982 not wanting to include whites in blend. Made from free run juice, it is co-fermented with dashes of Canaiolo Nero and Colorino then aged in large cask. Fragrant, fine and bright yet profound.

Sangiovese in purezza, Le Pergole Torte followed with the 1977 vintage, released as a table wine in 1980. While no longer a single vineyard, the backbone does hail from the eponymously named plot - planted in 1968 on iron-rich Galestro with a north/northeast exposure. Finished in used barriques, it is typically austere and linear though utterly refined.

Much more accessible on all fronts, the tactile and juicy Pian del Ciampolo should not be overlooked. it blends the press juice from Montevertine and Le Pergole Torte with lots from younger vines.

Today the estate’s wines conform perfectly with Chianti Classico regulations, Martino has no plans to return to the fold honouring the promise he made to his father. Martino’s nephew Tancredi Reimitz started 2021 and is poised to be successor.

Castello di Brolio sprawls over 1200 contiguous hectares throughout the district of Gaiole in the southeastern stretch of Chianti Classico. It has been in the Ricasoli family since at least 1141. This is not just any noble family. The Baron Bettino Ricasoli (who twice served as Italy’s Prime Minister) is credited with the ‘Chianti’ recipe – championing Sangiovese with a splash of Canaiolo to soften its hard edges.

Today the estate is led by Francesco Ricasoli. A photographer by profession, Francesco managed to take back the Castello di Brolio brand and winery in 1993 after they had been acquired by Seagram in the 60s. He has slowly rebuilt the reputation reducing production by focusing on estate rather than purchased fruit.

Among the early adopters of the Gran Selezione category, Ricasoli offers 3 site specific bottlings based on extensive soil studies. In the last couple of vintages, they demonstrate clearer and more distinct identities. However, it is the tradition Castello di Brolio bottling made from a selection of the best parcels that captures the soul of the estate. And, when it comes to value money, the annata is a perennial pick.

In 2025, Francesco’s daughter Sofia (a criminal lawyer) started showing an interest in the estate. Currently training in all facets of production, hospitality and sales, she is set to be the 33rd generation here.

If there is one winery that has put Chianti Rùfina on the global wine map, it is Selvapiana. Rather than its long history (the estate was established by the Giuntini family in 1827), it is the Bucerchiale bottling that catapulted Selvapiana into icon status. Debuting with the 1979 vintage, the wine was among the first quality-driven, rule-breaking 100% Sangiovese wines in the greater Chianti area - along with Montevertine’s Pergole Torte and Fontodi’s Flaccianello.

Bucerchiale has always hailed from the same plot – a southwest facing slope at 220 metres. Winemaking, however, has swung quite drastically during Federico Giuntini Masseti’s 30-plus-year tenure - from ultra-tradition to hyper-modern. Today the pendulum has settled elegantly in the middle without sacrificing its savoury and commanding soul. Federico’s oldest son Niccolò, who took over winemaking in 2019, seems committed to staying the course.

Launched with the 2016 vintage, Vigneto Erchi hails from a warmer south facing expanse at slightly lower altitudes. The calcareous limestone soil rich in iron gives a denser, more muscular expression. This has been selected for the new Terraelectae category which now sits at the top of the denomination’s quality pyramid.

The stalwart annata Chianti Rùfina generally offers great back for the buck.