There is a particular kind of afternoon that Tuscan red wine was invented for. Long table, dappled shade, a plate of pici with wild boar ragù, somebody's uncle telling a story that has clearly been told before. The wine is red, a little dusty, a little sour-cherry, and it disappears faster than anyone admits. It is the most famous wine region in Italy, and also one of the most misunderstood.

So here is everything you need to know about Tuscan reds, from Chianti to Brunello to the rebels who broke all the rules and became the most expensive wines in the country. It is simpler than it looks. Nearly all of it comes back to one grape.

It All Starts With Sangiovese

Sangiovese is Tuscany. It is the backbone of Chianti, the whole of Brunello di Montalcino, the heart of Vino Nobile di Montepulciano. One theory says the name comes from the Latin sanguis Jovis, the blood of Jupiter, which is a lot to live up to for a grape that mostly gets drunk with pasta.

What does it taste like? Sour cherries, dried herbs, tea leaves, a hint of leather and that faint, dusty earthiness that tastes like the Tuscan hills look in August. It has high acidity and firm tannins, which is why it is so good with food and occasionally a bit severe without it. Sangiovese is the friend who is brilliant company at dinner and slightly awkward at a drinks party. Feed it.

Chianti, Brunello and the Rest

Chianti Classico comes from the historic heartland between Florence and Siena and carries the black rooster on its neck. It is the everyday Tuscan red done properly: bright, savoury and built for the table. Brunello di Montalcino, from the warmer hilltop town to the south, is 100% Sangiovese and cannot be released until five years after the harvest. It is deeper, more brooding, more built to age; Tuscany's answer to a good Barolo. Vino Nobile di Montepulciano, from a different hill town nearby, sits somewhere between the two. (Not to be confused with Montepulciano d'Abruzzo, which is a different grape from a different region entirely. Italy enjoys confusing people.)

Then there is the Val d'Orcia, the UNESCO-listed valley of cypress avenues and rolling wheat fields that sits between Montalcino and Montepulciano. You have seen it on a thousand postcards. It is also home to Podere Forte, where Pasquale Forte has spent years restoring an ancient farm and making wine with obsessive care. Their Villaggio is a joyful, cherry-bright introduction; the Petruccino brings more depth and polish; and the Petrucci Melo 2015, given the patience of a decade, is Sangiovese in a velvet smoking jacket.

The Rebels: Super Tuscans

In the 1970s, Tuscany's rules were, frankly, a bit daft. Chianti had to include white grapes in the blend, which many producers felt diluted it. A few ambitious estates decided they would rather make the wine they wanted than the wine the rules required. They blended Sangiovese with Cabernet Sauvignon and Merlot, or abandoned Sangiovese entirely, and aged their wines in small French barrels. The authorities responded by classing these wines as vino da tavola: table wine, the humblest category in Italy.

Within a decade, these "table wines" were among the most expensive and sought-after bottles in the country. The press called them Super Tuscans, and the name stuck. The most famous of all is Sassicaia, born on the coast at Bolgheri when the Marchese Mario Incisa della Rocchetta planted Cabernet Sauvignon there in the 1940s, at first purely for his own table. It was so admired that Sassicaia now has a DOC of its own, Bolgheri Sassicaia, the only single estate in Italy with an appellation all to itself. The same family makes Guidalberto, a Cabernet and Merlot blend that gives you a taste of that coastal glamour for a fraction of the price of its famous sibling.

How to Drink Tuscan Reds

Serve them slightly cooler than room temperature, around 16 to 18°C. Younger Chianti and Rosso can go straight into the glass; Brunello and the bigger Super Tuscans reward an hour in a decanter, especially in their youth. And always, always with food. Tomato-based pasta, bistecca alla fiorentina, wild boar, aged pecorino, a plate of salumi. Sangiovese's acidity cuts through fat and stands up to tomato in a way few other reds can manage, which is why it has been the wine of Italian kitchens for centuries.

By the Case

Tuscany, by the case: Podere Forte, Guidalberto and Brunello Riserva in one mixed six, or six of a single wine. Quantities are fixed.

• The Tuscan Collection: six bottles, £477.99 (15% off). Buy now
• Podere Forte, Petruccino 2020: six bottles, £231.99 (10% off). Buy now
• Tenuta San Guido, Guidalberto 2023: six bottles, £312.99 (10% off). Buy now

Each Buy now link opens a pre-filled email to Patrick in our team at pdiggins@houseofdecant.com. Change the quantity if you like and press send.

The Insider

Five things to know before the next long lunch.

• Chianti's black rooster comes from a medieval legend. Florence and Siena agreed to settle their border by sending riders towards each other at the first cockcrow. The Florentines starved their black rooster, it crowed long before dawn, and Florence won most of Chianti.
• The first Super Tuscans were legally classed as table wine, the lowest rung of Italian wine law, while selling for more than almost anything else in Italy.
• Sassicaia began as a private experiment. Its first vintage to be sold commercially was 1968, more than twenty years after the vines were planted.
• Brunello di Montalcino cannot go on sale until five years after the harvest. Montalcino invented the long game.
• Sangiovese is the most planted red grape in Italy. If you have ordered the house red in an Italian restaurant, there is a fair chance you have been drinking it without knowing.

The Long Lunch Test

The best way to understand Tuscan red is the way the Tuscans do: slowly, at a table, with something good to eat. Open a bottle from the hills and a bottle from the coast. Taste the sour cherry and herbs of Sangiovese next to the plush blackcurrant of a Bolgheri blend, and you will understand five centuries of argument in about five minutes.

Then pour another glass and let the uncle finish his story. He has earned it, and so have you.