The Tuscan Wine Guide: What to Drink and Where to Go
Chianti, Brunello, Vino Nobile, Super Tuscans—and even a few whites. Here’s how to make sense of Tuscany’s wine regions, whether you’re planning a day of tasting or simply trying to order a bottle with dinner.
I couldn’t spend a week talking about Florence on Instagram without talking about wine. After all, a Florentine experience isn’t complete without the food and wine.
We all dream about tasting wine in Tuscany. But unless you’re already a serious Italian wine drinker, most of us arrive knowing little beyond Chianti and maybe Super Tuscans.
A couple of years ago, Jake and I were fortunate enough to spend time in Florence visiting wineries and tasting some fantastic Tuscan wines with our local Florentine friends—who also happen to be serious wine connoisseurs.
And one thing becomes clear pretty quickly: Tuscan wine isn’t one thing.
You can drink Sangiovese in Chianti Classico, drive farther south and drink 100% Sangiovese in Montalcino, encounter yet another expression of Sangiovese in Montepulciano—and then head toward the coast to Bolgheri, where Cabernet Sauvignon, Cabernet Franc, and Merlot helped turn traditional Tuscan winemaking on its head.
So here’s my basic Tuscan wine guide and cheat sheet: four regions, what to drink, where to go and a few wineries worth putting on your list.
Chianti Classico: The Classic Tuscany
If this is your first trip to Tuscany, Chianti Classico is a wonderful place to start. Stretching between Florence and Siena, this is the Tuscany most of us have in our heads: rolling vineyards, olive groves, cypress trees, stone farmhouses and medieval villages. And at the center of the wine is Sangiovese. Sangiovese gives Chianti Classico its characteristic bright cherry fruit, savory herbs, earthy notes and, importantly, acidity. That acidity is one reason these wines are so good at the table. A good Chianti Classico beside a plate of pasta with wild boar ragù or a bistecca alla Fiorentina makes immediate sense. And because the region begins just south of Florence, it’s also the easiest of these areas to experience as a day trip.
Wineries of Note:
Antinori nel Chianti Classico
The Antinori family has been making wine for more than six centuries, but their Chianti Classico winery is anything but old-fashioned. The contemporary winery is built almost entirely into the hillside, with enormous glass windows, sweeping horizontal lines, and its unmistakable spiral staircase. It feels as though someone sliced open the Tuscan hillside and put a winery inside it. But Antinori is more than great architecture. The family also played an important role in changing modern Tuscan wine.
If you have the opportunity, try Tignanello. Tignanello is predominantly Sangiovese blended with Cabernet Sauvignon and Cabernet Franc. Its development in the 1970s challenged some of the conventions governing traditional Chianti production and helped usher in a new era of Tuscan winemaking. Ironically, one of the wines most closely associated with the Chianti Classico countryside isn’t labeled Chianti Classico at all.
Castello di Ama
For a completely different experience, there’s Castello di Ama. The estate occupies a centuries-old hamlet surrounded by vineyards, but what makes a visit particularly interesting is the contemporary art incorporated throughout the property. This isn’t art hung on tasting-room walls as decoration. Castello di Ama has commissioned site-specific works from major contemporary artists, making the estate as much an art destination as a wine destination. Come for the excellent Chianti Classico. Give yourself enough time to explore the art.
Fontodi
For someone who really wants to understand what Sangiovese can do, I’d also put Fontodi on the list. The estate lies in the Conca d’Oro—the “golden shell”—near Panzano, one of the particularly prized areas of Chianti Classico. Fontodi is also the producer of Flaccianello della Pieve, a 100% Sangiovese wine that offers an interesting counterpoint to Tignanello. Taste the two, and you begin to understand just how many directions Tuscan winemakers can take the same grape.
Castello di Fonterutoli
The Mazzei family has centuries of history in Chianti Classico, making Castello di Fonterutoli another wonderful stop if you want history alongside the wine. The estate combines an old Tuscan village with a striking contemporary cellar built into the hillside. It's also a particularly appealing place to linger rather than simply taste and leave. Wine country should include lunch whenever possible.
If you have only one wine day from Florence, Chianti Classico is probably where I’d begin.
Montalcino: The Home of Brunello
Now drive farther south. The grape is still Sangiovese. The wine is very different.
Brunello di Montalcino is made from 100% Sangiovese, historically known locally as Brunello. These wines are generally deeper, more structured, and built for considerably more aging than the Chianti Classico you may have tasted the day before. And I mean aging. I recently had a 1993 Il Palazzone Brunello di Montalcino at a dinner party. More than 30 years after the vintage, it was a wonderful reminder of what well-made Brunello can become with time.
Wineries of Note:
Biondi-Santi
You really can’t tell the story of Brunello without talking about the Biondi-Santi family.
Their work with Sangiovese at the Greppo estate in the late 19th century helped establish the long-lived style of wine that would eventually become Brunello di Montalcino.
So Biondi-Santi isn’t simply another prestigious Brunello label. The family is woven into the history of Brunello itself.
Casanova di Neri
Casanova di Neri gives you a fascinating contrast. Founded much later, the estate became one of Montalcino's celebrated modern names and is associated with a richer, more contemporary expression of Brunello. This is part of what makes spending a full day in Montalcino worthwhile. Brunello doesn’t have one single taste. Producer, vineyard, vintage, and winemaking style all matter.
Poggio di Sotto
For the serious Brunello drinker, Poggio di Sotto belongs on the list. The estate focuses intensely on Sangiovese and is known for traditional, elegant, and highly age-worthy Brunello. This is less about spectacle and more about the wine itself—which is exactly what some wine travelers want.
Col d’Orcia
Col d’Orcia gives you yet another expression of Montalcino. The historic estate lies south of town and encompasses vineyards, olive groves and farmland. It’s a particularly good choice if you want the tasting to feel connected to the broader agricultural landscape of southern Tuscany rather than simply visiting a cellar.
And I wouldn’t try to squeeze Montalcino into a hurried half-day from Florence. Give it the day. Drive through the countryside. Have lunch. Walk through Montalcino. Taste Brunello. The journey is part of the experience.
Montepulciano: The Noble Wine of Tuscany
First, let’s clear up one of Italian wine’s more confusing naming problems. Vino Nobile di Montepulciano is NOT made from the Montepulciano grape. The Montepulciano grape is associated primarily with other parts of central Italy, most famously Abruzzo. In the Tuscan town of Montepulciano, we’re back to Sangiovese, locally known as Prugnolo Gentile. The resulting Vino Nobile di Montepulciano can be elegant, earthy, and beautifully structured.
And these wines have serious history. Montepulciano’s wine had an exalted reputation long before modern wine classifications existed. In his 1685 poem Bacco in Toscana, Francesco Redi famously proclaimed Montepulciano the “king of all wines.” There’s also a connection to the Medici story. Montepulciano came under Florentine control and eventually became part of the Medici-dominated Tuscan state. Florence’s influence can still be felt in the Renaissance architecture of the town. But what makes Montepulciano especially compelling for a traveler is that the town itself is every bit as interesting as the wine.
Wineries of Note:
De’ Ricci
At De’ Ricci, the wine experience takes you underground. Its extraordinary historic cellars extend beneath the family’s Renaissance palazzo in the center of Montepulciano. Descending into them makes the relationship between the town and its wine physically tangible. You aren’t visiting an isolated tasting room outside town—you’re literally underneath centuries of Tuscan history.
Avignonesi
Avignonesi offers a very different experience. With vineyards and an estate outside the historic center, it’s one of the better-known modern names in Vino Nobile and has become particularly associated with organic and biodynamic farming.
Boscarelli
Boscarelli is a more intimate, family-run choice and one I’d consider for someone whose priority is the wine rather than a grand estate. Its wines tend toward a more classic, refined expression of Vino Nobile, making it an interesting counterpoint to some of the region’s larger producers.
Poliziano
And then there’s Poliziano, one of the important modern producers that helped elevate the reputation of Vino Nobile.
Together, these four offer very different ways to experience Montepulciano: historic underground cellars, a beautiful vineyard estate, an intimate family producer, and a modern benchmark. If your ideal Tuscan wine day involves a great bottle, a beautiful lunch and several hours wandering through a spectacular hill town, Montepulciano may be your answer.
Bolgheri: Where Tuscany Broke the Rules
And now we leave Sangiovese behind. Head west toward the Tuscan coast, and you reach Bolgheri, where the wine story looks surprisingly different. Here, winemakers began working with Cabernet Sauvignon, Cabernet Franc and Merlot—grapes we associate much more readily with Bordeaux than traditional Tuscany.
The result? Sassicaia. Ornellaia. And the phenomenon we now associate with the Super Tuscans.
The Sassicaia Story
Sassicaia is where this story really begins. In the mid-20th century, Marchese Mario Incisa della Rocchetta planted Cabernet at Tenuta San Guido. The wine was initially made largely for private family consumption. Eventually, Sassicaia was commercially released, and its success helped demonstrate that extraordinary Tuscan wine didn’t necessarily have to follow Tuscany’s established winemaking rules. That’s important to understanding the term Super Tuscan. It wasn’t originally a formal appellation. It became a way of describing ambitious Tuscan wines that didn’t fit neatly into the traditional classification system—often because their producers were using international grape varieties or blends that regulations didn’t permit.
Tenuta San Guido
Tenuta San Guido therefore belongs on any list of Bolgheri estates to know, even though it isn’t the sort of winery where you simply turn up for a conventional tasting. This is the home of Sassicaia, and its importance to Bolgheri's story is difficult to overstate. Even if you never visit the estate itself, drink Sassicaia while you’re here if the opportunity presents itself.
Ornellaia
Ornellaia followed in the 1980s and became another defining name in Bolgheri. Its flagship wine is built around Bordeaux varieties, and the estate has also developed an interesting relationship with contemporary art through its Vendemmia d’Artista project.
If you have the opportunity, of course try Ornellaia. But also look for Le Serre Nuove dell’Ornellaia, the estate’s second wine. It can be a wonderful introduction to the style and philosophy of the estate without beginning with the trophy bottle.
Le Macchiole
Le Macchiole is another important Bolgheri producer, but with a somewhat different philosophy. One wine particularly worth knowing is Paleo Rosso, made from Cabernet Franc. It’s a fascinating example of just how well a grape associated with Bordeaux can express itself on the Tuscan coast.
Guado al Tasso
Finally, Guado al Tasso brings us back to the Antinori family, this time on the coast.
The estate sits within the Bolgheri amphitheater and produces Bordeaux-style reds as well as something that becomes increasingly appealing after several days of tasting Tuscan reds: white wine. Which brings us to our bonus round.
Bonus: What About Tuscan White Wine?
After Chianti, Brunello, Vino Nobile and Bolgheri, you could be forgiven for thinking Tuscany is exclusively red-wine country. It isn’t. And there’s one Tuscan white in particular that I think travelers should know.
Vernaccia di San Gimignano
Yes, that San Gimignano—the medieval hill town famous for the towers rising above its skyline. The countryside surrounding San Gimignano produces Vernaccia di San Gimignano, Tuscany’s great historic white wine. And Vernaccia has been famous for a very long time. It was known in medieval Italy and even appears in Dante’s Divine Comedy. Centuries before Tuscany became an international wine-tourism destination, people were already talking about the white wine of San Gimignano.
In the glass, Vernaccia is a completely different experience from the reds we’ve been discussing. Expect freshness rather than power: citrus, orchard fruit, herbs and minerality, often with a characteristic slightly bitter almond note on the finish. Better examples—and particularly Riservas—can also have surprising structure and the ability to age.
And San Gimignano makes this a particularly appealing wine day because, once again, the wine is only half the reason to go. Explore the town. Have lunch. Then head into the surrounding countryside to taste Vernaccia.
Panizzi
Panizzi is one of the names I’d look for if the wine itself is your priority. The estate has played an important role in the modern reputation of Vernaccia, and its Riserva is particularly worth seeking out.
Cappella Sant’Andrea
For something smaller, Cappella Sant’Andrea is an organic producer working with old vines and interesting approaches to aging Vernaccia. This is the kind of stop I’d choose for someone who has already tasted the obvious wines and wants to dig a little deeper.
Fattoria San Donato
Fattoria San Donato appeals to me for another reason: it offers more than a tasting.
It’s a family-run organic farm in a tiny medieval village, surrounded by vineyards, olive groves and farmland. This is the Tuscany where wine is part of an agricultural way of life, not an isolated luxury product.
Tenute Guicciardini Strozzi
And then there’s Tenute Guicciardini Strozzi, where the family history stretches back centuries. There’s even a wonderful Florentine connection: the family tree is connected to Lisa Gherardini, traditionally identified as the woman depicted in Leonardo da Vinci’s Mona Lisa. Wine, Renaissance Florence and a little art history all in one stop?
And Vernaccia Isn't Tuscany's Only White
If you’re heading toward the coast, also look for Vermentino. You’ll encounter it around Bolgheri and elsewhere along the Tuscan coast, where its freshness is particularly welcome beside seafood—and after several days of Sangiovese and Cabernet.
At an estate such as Guado al Tasso, tasting Vermentino alongside the reds is also a wonderful reminder that even within one Tuscan wine region, there’s more variety than we sometimes expect.
So, Which Tuscany Is Your Tuscany?
The Tuscan Wine Guide and Cheat Sheet
Region | Key Grape | Wine Style | Best For |
Chianti Classico | Sangiovese | High acidity, cherry, earthy | First-timers & food pairing |
Montalcino | Sangiovese | Bold, structured, highly aged | Serious red wine lovers |
Montepulciano | Sangiovese (Prugnolo Gentile) | Elegant, balanced, historic | Wine + medieval hill town vibe |
Bolgheri | Cab Sauvignon, Cab Franc, Merlot | Rich, Bordeaux-style "Super Tuscans" | Lovers of bold Cabernet |
San Gimignano | Vernaccia | Crisp, citrusy, mineral white | A break from heavy reds |
Tuscan Coast (The Maremma) | Vermentino | Fresh, aromatic, citrus & herbal white | Pairing with seafood on the coast |
Of course, there’s another perfectly reasonable option:
Plan an entire trip around exploring all of them. I certainly wouldn’t argue with that.
And even if you never set foot inside a winery, understanding these regions makes sitting down at a restaurant in Florence considerably more fun. When the wine list arrives, Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano, Bolgheri and Vernaccia di San Gimignano suddenly mean something. You know roughly what you're getting. You know where it came from. And perhaps you know which bottle you're excited to order.
Because the best Tuscan wine itinerary—or even just the best bottle with dinner—starts with one question: What do you love to drink?
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