Plan on a minimum of two weeks here; this is not a place to fast-forward through. In Tuscany, you take your time, give in, and never resist temptation – this is where you learn the true meaning of slow travel. You really need the time to live it, not just visit it, and once you do it properly, you’ll find there’s no place quite like it.
Intel
Best time to visit: September.
Transport: fly into Pisa or Florence and then rent a car – this is non-negotiable. Tuscany has the most beautiful medieval castles and villages, plus the most wonderful country roads. If you can’t freely move between those vineyards and properly take in the iconic cypress-lined landscape, don’t even say you’ve been to Tuscany.
Where to stay: a Tuscan farm/villa. My choice is an old farm, full of character and surrounded by olive trees and vineyards in Chianti, ideally close to Siena.
ONE: FLORENCE
Probably the most beautiful city in the world, Florence is a universe in itself. Here, the Renaissance was born, and here, your journey truly begins. Essential Firenze here.
TWO: THE CHIANTI CLASSICO REGION
From Florence, your journey takes a distinct turn. You enter the Chianti Classico Region, the true heart of Tuscany, historically bounded between Florence and Siena. This is the legendary land of the Black Rooster (Gallo Nero). This ancient symbol, born from a medieval rivalry, now marks every authentic bottle in this DOC, guaranteeing a wine crafted exclusively within these rolling hills.
Here, Sangiovese reigns supreme. For a Chianti Classico wine, it must be at least 80% Sangiovese, defining its robust character and signature acidity. Look closer, and you’ll find tiers: the standard Classico, the aged Riserva, and the pinnacle, Gran Selezione, each based on centuries of winemaking mastery.
The Chianti Classico region lies primarily between Florence and Siena, but dont take the highway, take the Chianti way instead. The Chiantigiana (SR 222) is your essential guide through this story. It snakes past sun-drenched vineyards and olive groves, leading to iconic hilltop villages like Greve, Panzano, Gaiole, Castellina, and Radda, all inviting genuine discovery.
But forget the checklist; the real Chianti Classico experience demands instinct. Pull into an unassuming cantina for a tasting direct from the barrel, find a hidden trattoria with homemade pasta, or claim a spot in an old village piazza – a natural balcony – soaking in the rolling hills stretched below. This is slow travel perfected.
THREE: PIENZA AND VAL D’ORCIA
That step-into-the-postcard feel: Val d’Orcia. This UNESCO World Heritage site is famed for its iconic, over-photographed rolling hills and golden fields punctuated by solitary cypress trees and ancient farmhouses. At its heart lies Pienza, the flawless Renaissance ideal town, meticulously designed, yet very much alive. Wander its charming streets, set your photo session on Via dell’ Amore, but don’t forget your Pecorino cheese.
FOUR: MONTALCINO & MONTEPULCIANO
These are the red twins: two incredible fortress towns defined by their legendary red wines. The serene and often sunnier Montalcino is home to Brunello di Montalcino, a 100% Sangiovese wine famed for its minimum 5 years aging (2 in oak) for standard Brunello, 6 for Riserva. This is where patience rewards: seek out a quiet enoteca for a vertical tasting of Brunello vintages.
Next, Montepulciano at sunset. A town of dramatic, steeper ascents, its character mirrors its prized Vino Nobile di Montepulciano: dry, noble, a Sangiovese-dominant wine aged for a minimum of 2 years (1 in oak), 3 for Riserva. Climb its main street, the Corso, winding up to the Piazza Grande, lined with grand palaces. Beyond the main Corso, Montepulciano’s winding alleys reveal hidden artisan shops, quiet courtyards, and unexpected viewpoints. These are the true veins of the town, offering glimpses of local life away from the main tourist flow. For a true treasure, dig deeper: below ground, a network of ancient cellars holds noble Montepulciano’s secrets, its wines, and its ghosts. Do explore La Citta Sotterranea!
FIVE: CORTONA
Cortona is a great city to spend a few days in this remote area bordering Umbria. The old city is clinging to a hillside at over 600 meters above the Valdichiana, in the region made famous by Under The Tuscan Sun. From its heights, panoramas unfold across the plains, Lake Trasimeno and distant mountains.
Old Cortona is quite formidable. It’s worth the trip just for a stroll on the Via Nazionale, a drink in Piazza Republica, some fragrance shopping at Essenza di Cortona, a visit to Circle of Life art gallery, and a quiet moment in Piazza Signorelli and Piazza Duomo. Many come for dinner; its food scene is fantastic.
But for the happy few who spend a few days here, a higher level Cortona awaits. Its steep, winding streets, often too narrow for cars, go up and up. This town demands a real climb, but the reward is incredible historical findings, peaceful, almost monachal oases, and great vistas. Climb higher to the Basilica di Santa Margherita and the Fortezza di Girifalco for the ultimate vantage points, and retrace the steps of Under the Tuscan Sun at the famous Villa Bramasole.
SIX: VOLTERRA & SAN GIMIGNANO
Ah, San Gimignano, Toscana’s medieval Manhattan! Its iconic towers form an unmistakable skyline that has earned it UNESCO World Heritage status. Once numbering 72, the remaining towers are proof of a medieval, vertical competition for wealth and power between the town’s rival families. Be warned: their fame draws relentless crowds. For the happy few, however, a relaxed visit and a glass of Vernaccia di San Gimignano, the white wine of crisp, singular character, is enough.
I often pair Volterra with San Gimignano because of their relative proximity and their contrasting character: one ancient and quiet, the other ambitious and loud. Volterra rises on its dramatic bluff, a town of stark, Etruscan origin built on rock and the shadows of history. Yet it is also the city of alabaster, a luminous craft that continues today, as for centuries artisans have worked the translucent stone pulled from the hills. Walk the streets and peer into the workshops of alabaster artisans. Descend to the ruins of the 1st-century Roman amphitheater. Make time for the Guarnacci Etruscan Museum, home to the one-of-a-kind Ombra della Sera. Above it all, the formidable Fortezza Medicea. This is a place for longer exploration, where you can always find corners away from the hurried paths of mass tourism.
SEVEN: AREZZO
It is not a pristine hilltop town and won’t lead your usual top-ten lists. Arezzo is a true find, a city with a memorable feel of lived-in authenticity. For the happy few, the pilgrimage here is for the art of Piero della Francesca, and specifically for the breathtaking Basilica of San Francesco, where his Legend of the True Cross fresco unfolds like a sacred graphic novel.
Beyond the art, you’ll find superb streets and parks, the great Duomo right next to the gardens of the Medici Fortress, a focus on slow food, and a familiar feeling you can call home. Arezzo’s ultimate, irresistible mark, however, is its magnificent, sloping Piazza Grande. A dramatic, asymmetrical stage framed by medieval and Renaissance architecture, it’s a place to linger with an aperitivo. If you time your visit right, you will catch the monthly Fiera Antiquaria, Italy’s largest antique fair, where the piazza transforms into a treasure trove of forgotten things. This city rewards those who look beyond the obvious, offering a masterclass in quiet, enduring beauty.
EIGHT: SIENA
The Republic of Siena retains its proud, autonomous spirit, with loyalty to its traditions and the greatest quality of life in Tuscany. The Duomo is a masterpiece of Gothic art with a glorious marble-striped interior, featuring what is probably the most beautiful pavement ever. Siena’s medieval heart beats strongest in the magnificent, shell-shaped Piazza del Campo, the red brick city lounge that has been the soul of the city for centuries. Here, the Torre del Mangia stands watch over the daily life and offers stunning views from the top.
Most know Siena for the Palio, the bareback horse race that rips through the piazza twice a year, in July and August. The city’s true nature lies in the rivalries of its 17 contrade, or city districts, whose vibrant banners hang from every window. So, come for the Palio and, even more important, the dinner after, in the streets of the contrade. As the celebrations spill from the piazza, the victorious contrada transforms its streets into a true open-air banquet. Long tables are set up right on the cobblestones, stretching through the winding alleys as every member, from the oldest elder to the youngest child, gathers to feast. What many don’t know is that all ten contrade that are running the race have a communal dinner, known as the “Cena della Prova Generale,” on the evening before the race – so be there.
NINE: THE WINE AND THE FOOD
Straightforward and best in the world: this is how you will remember Tuscan food. Keeping the beautiful Italian tradition of simplicità, the food is made of simple ingredients, true and satisfying. In Firenze, bistecca fiorentina is meant as a masterpiece to be reveled in on the same level as the masterpieces of the Ufizzi. I for myself, I’m not the rare meat lover, so I skip that staple, but a Lampredotto sandwich from a street cart in Florence is part of the rite of passage. Street food is often better than many tourist taverns, so go for a schiacciata.
And then throughout Tuscany, you’ll find the region’s treasures: incredible cheeses, particularly the sharp, salty Pecorino Toscano served with honey or jam; a bottle of red; the salame di cinghiale; the unsalted bread, pane sciocco, used to soak up rustic soups like Pappa al Pomodoro or Fagioli all’uccelletto, the bean stew. These simple, unpretentious dishes are a remnant of cucina povera, the poor Italians’ wisdom of cooking, that it is now treasured for its sustainable philosophy “make more with less”.
On the hearty side, the wild boar, Cinghiale, is a leitmotif of the area. You’ll find it in rich stews, in the ragu, as a mascot here and there for a shop of prodotti tipici, on souvenirs and T-shirts, and even running freely on the unpaved roads between vineyards.
As for the wines, lets just say this is not just wine country, but the wine country. All of Tuscany’s noble reds are expressions of the same stubborn Sangiovese grape, yet their character shifts with the land. Your everyday table wine is a Chianti Classico, its bright acidity a perfect counterpoint to hearty meals. You’ll find elegant refinement in a Vino Nobile di Montepulciano, but no two Nobile are alike. The VIP, Brunello di Montalcino, lives up to its name and the occasion, but the key is not to have the most expensive bottle, but to try as many stories of the terroir in as many glasses.
