2. Siena: a Medieval masterpiece
Siena rises in amber and brick, its rooftops spiraling around Piazza del Campo, a scallop-shaped square built in the 13th century, still home to the heart-stopping Palio horse race. The tradition has run uninterrupted since 1633, though its roots trace back to earlier medieval contests held elsewhere in the city.
Inside the 13th-century Siena Cathedral, striped marble columns draw the eye upward, while the inlaid floor beneath your feet, one of the most elaborate in Italy, tells stories from the Old Testament to pagan antiquity. Beyond the piazza, narrow streets twist past Gothic windows and noble palazzi, opening onto views of olive groves and the hills that stretch toward the Val d’Orcia.
3. Val d’Orcia: a painter’s paradise
Some landscapes feel imagined. Val d’Orcia is not one of them.
This UNESCO World Heritage site is a living fresco of sculpted hills, solitary cypress trees and weathered stone farmhouses. For centuries, painters tried to capture its balance and serenity; today, travelers come to witness the real thing.
Along winding roads and golden slopes, towns like Montalcino echo with silence and permanence. The vineyards here yield Brunello, a deep, complex wine shaped by the valley’s unique soil and slow rhythms.
4. Pienza: the ideal city, perfectly real
In the 15th century, Pope Pius II transformed his Tuscan birthplace into something new: a city shaped by harmony, proportion and humanist ideals. The modest village of Corsignano became Pienza, one of the earliest and purest expressions of Renaissance urban planning.
From Piazza Pio II to the elegant Palazzo Piccolomini and its garden overlooking the Val d’Orcia, the town feels like a manifesto carved in stone. And yet, Pienza remains intimate. Its streets open toward golden terraces above the valley, where the light shifts from gold to silver.
Sit along Via dell’Amore (Love street) and you’ll feel it: this is a place where utopia was not just dreamed; it was built to be lived in. For this, Pienza is one of the best places to go in Tuscany for those who seek beauty shaped by human vision.
5. San Gimignano: the town of fine towers
Approaching San Gimignano, the towers rise like a medieval skyline. In the 13th century there were more than 70, symbols of power, pride and rivalry. Today, 13 remain, casting long shadows over the elevated town and earning it its nickname: the Manhattan of the Middle Ages. Beneath these stone sentinels, time seems to pause here.
The Torre Grossa, still the tallest, offers views that stretch across vineyards and olive groves. Inside the Collegiate Church, frescoes by artists like Ghirlandaio retain their color and grace, offering a glimpse into a world long gone. And in a quiet piazza, a glass of Vernaccia, Tuscany’s first DOC white wine, carries the crisp, mineral echo of the land.
6. Chianti: wine country at its finest
Between Florence and Siena, the hills shift to a gentler cadence. This is Chianti, one of the best places to go in Tuscany for wine lovers. Here vineyards spread across the land and olive groves frame sun-warmed villages.
The Chianti Classico zone, marked by the iconic black rooster, has produced DOCG wines since the 13th century. Towns like Radda, Castellina and Greve preserve that legacy in weathered wine cellars, quiet piazzas and rustic enoteche (traditional wine bars) that still serve the season’s best.
7. Lucca: a city within its walls
Encircled by Renaissance walls that now cradle tree-lined paths and quiet views, Lucca holds its treasures close.
Within the walls, Romanesque churches like San Frediano and San Michele in Foro speak of devotion and civic pride. On Via Fillungo, the city’s main street, bakeries and antique shops sit behind medieval façades. And from the top of Torre Guinigi, crowned with ancient oaks, rooftops stretch to the distant Apuan Alps.
In Lucca, life unfolds at a gentle pace. Locals cycle past marble fountains, children play in shaded courtyards and music drifts from hidden conservatories.
8. Montepulciano: a toast to the Renaissance
Perched high above the Val di Chiana, Montepulciano rises in terraces of warm stone and vineyards that ripple down the hillsides. Its Renaissance streets lead to Piazza Grande: a splendid square framed by palazzi that have seen centuries pass.
Beneath them, ancient cellars carved into the rock cradle barrels of Vino Nobile di Montepulciano, one of Italy’s oldest and most esteemed red wines.
From the Renaissance elegance of Palazzo Comunale to the quiet ritual of tasting that wine in the vaulted rooms below, Montepulciano invites you to savor Tuscany at its richest.
9. Pisa: beyond the leaning tower
The Leaning Tower is Pisa’s most famous face, but the city offers more than this iconic monument.
The Piazza dei Miracoli (literally Square of Miracles, officially Piazza del Duomo) dazzles with its striking white marble cathedral, baptistery and campanile (the bell tower), all showcasing Pisa’s historic wealth and artistic mastery.
Beyond the square, the Arno River flows through a vibrant university town, where lively markets bustle, bookshops invite exploration and locals savor coffee beneath the shade of elegant arcades.
10. Montelupo Fiorentino: where ceramics still sing
Just outside Florence, Montelupo Fiorentino has shaped clay into art for over 500 years.
Its rich deposits of local clay fueled centuries of craftsmanship, making it one of Italy’s most important centers for maiolica, the vividly painted pottery that once adorned palaces and churches across Europe.
Today, the tradition endures. Artisans still mix pigments by hand and fire their creations in wood-fired kilns. The Ceramics Museum traces this legacy with masterpieces from the 14th century to today, telling a story of art, trade and culture deeply woven into the town’s identity.
The many layers of Tuscany’s beauty and tradition
Tuscany reveals itself slowly. It’s more than just a list of the best places to go: it’s a mosaic of traditions, gestures and craft. In Florence’s markets, in the hush of a vaulted cellar or the quiet between towers, this region speaks in details.
