The Most Beautiful Places in Tuscany (And Why Everyone Falls in Love With Them)
There are regions of the world that seem almost wilfully beautiful — as though they've been arranged by someone with an impossibly refined eye. Tuscany is one of them. The rolling hills, the cypress avenues, the hilltop towns rising from morning mist, the vineyards in autumn light — it all looks exactly as it does in the paintings. Which makes sense, because the paintings came first. Tuscany has been inspiring artists for seven hundred years, and standing in the landscape you understand immediately why.
Here are the most beautiful places in Tuscany — from the world-famous to the breathtakingly overlooked.
1. Val d'Orcia
The most photographed landscape in Tuscany and arguably in all of Italy, the Val d'Orcia is the rolling green-and-golden valley south of Siena that appears in virtually every image of the Tuscan countryside. Cypress-lined roads curling over gentle hills, isolated farmhouses on ridgelines, fields of sunflowers and wild poppies, the extraordinary quality of light on a late afternoon in early summer — this is Tuscany at its most elemental and most beautiful. It's a UNESCO World Heritage Site, a recognition of a landscape so human in scale and so visually coherent that it represents centuries of civilised land management as much as natural beauty.
2. Siena
If Florence is Tuscany's brain, Siena is its heart. The medieval city on a hill above the Val d'Elsa is one of the great cities of the Middle Ages — still entirely intact, still surrounded by its original walls, its skyline dominated by the striped marble tower of the Palazzo Pubblico rising beside one of the most extraordinary public spaces in Europe. The Piazza del Campo, the shell-shaped central square where the Palio horse race has been run twice a year for seven hundred years, is one of those spaces that physically changes your breathing when you step into it. Siena in the early morning, before the tourists arrive, is as close to medieval Italy as anything alive today.
3. San Gimignano
San Gimignano's famous towers — fourteen remaining from an original seventy-two, built by competing noble families in the twelfth and thirteenth centuries as symbols of wealth and power — are visible from miles away, rising above the Chianti hills like a medieval Manhattan. The town itself is small and perfectly preserved, its stone streets lined with saffron merchants and vernaccia wine shops, and the views from the walls across the Elsa valley are some of the finest in Tuscany. Come in the late afternoon when the light goes gold and the towers cast long shadows across the square.
4. Florence
No list of beautiful places in Tuscany could leave out its capital. Florence is overwhelming in the best possible way — a city where Renaissance masterpieces are so densely concentrated that you become, after a while, somewhat blasé about walking past a Donatello on your way to lunch. The Duomo and its terracotta-tiled dome remain one of the great achievements of European architecture. The Ponte Vecchio at sunset is one of the most romantic sights in the world. And the Piazzale Michelangelo, the hilltop viewpoint above the city where the whole of Florence spreads before you in the evening light, is an experience that stays with you for years.
5. Pienza
Built in the fifteenth century by Pope Pius II as a model Renaissance town — his dream of what a perfect city should look like — Pienza sits on a hilltop above the Val d'Orcia with views that seem almost implausibly perfect. The main street, the Corso Rossellino, runs the entire length of the town in a few minutes and contains the cathedral, the Palazzo Piccolomini and the best pecorino cheese in Tuscany, all within comfortable walking distance. The well at the end of town looks out over the valley with a simplicity that photography struggles to capture and memory holds perfectly.
6. Volterra
More austere and less visited than its Chianti neighbours, Volterra sits on a dramatic plateau above steep valleys, its ancient Etruscan walls and medieval towers visible for miles across the surrounding countryside. This is older Tuscany — the city predates Rome — and it has a different character from the wine-country villages of the south. The alabaster workshops that have been here since antiquity are still producing bowls and lamps and sculptures from the stone quarried in the hills nearby. The Roman theatre below the walls, with its perfectly preserved stage and seating, is one of the finest in Italy.
7. Lucca
Completely encircled by its Renaissance walls — which have been converted into a tree-lined promenade wide enough to cycle on top of — Lucca is the most liveable of all Tuscan cities. Where Siena and San Gimignano feel like museums of themselves, Lucca is a real city that happens to be extraordinarily beautiful: excellent restaurants, a thriving market, Puccini's birthplace (he was a local), and a rhythm of daily life that feels thoroughly Italian rather than tourist-facing. The view from the Torre Guinigi — a medieval tower with trees growing from the top — over the honey-coloured rooftops is one of the great hidden sights of Tuscany.
8. Montalcino
Perched on a hilltop above the Val d'Orcia, Montalcino is the home of Brunello — arguably Italy's greatest red wine — and the town wears this distinction with quiet pride. The medieval fortress at the top of the hill, with a wine bar inside its walls, looks out over vineyards in every direction. The town itself is small and unhurried, with a handful of excellent restaurants and enotecas that take their wine seriously. In October, when the vineyards turn amber and russet and the light drops low, Montalcino is one of the most beautiful places in all of Italy.
9. Cortona
Made famous to the English-speaking world by Frances Mayes' Under the Tuscan Sun, Cortona sits high on a hillside above the Valdichiana with views across to Lake Trasimeno and the Umbrian hills beyond. The steep streets and wide piazzas of the old town are exactly as described in the book — warm stone, Etruscan walls, the smell of bread and coffee drifting from the cafes in the morning. The Museo Diocesano contains one of the greatest paintings of the Annunciation ever made, Fra Angelico's masterpiece, displayed in a room so quiet you can hear the floor creak.
10. Pitigliano
Perhaps the most dramatic townscape in Tuscany, Pitigliano rises from a plateau of volcanic tufo rock like something from a fantasy novel — a medieval city balanced on the edge of a cliff, its buildings so integrated into the rock that it's difficult to tell where the stone ends and the town begins. This is the Maremma, the wilder southern corner of Tuscany, and it has a rawer, less manicured beauty than the Chianti hills to the north. The town was once home to a significant Jewish community, and the 16th-century synagogue and Jewish ghetto, known as la piccola Gerusalemme, is a remarkable piece of history preserved in these extraordinary streets.
11. Montepulciano
Another hilltop wine town, another set of impeccable Renaissance streets, another piazza with views that make you feel the world makes sense. Montepulciano is the home of Vino Nobile, one of Tuscany's great red wines, and the town's cantinas — some of them in tunnels carved into the tufo beneath the streets — offer tastings in stone rooms unchanged for centuries. The Piazza Grande at the top of the town, with its well and its cathedral and its views over the surrounding countryside, is one of the finest public spaces in Tuscany.
12. The Chianti Countryside
The Chianti Classico wine region between Florence and Siena is not a town but a landscape — and it's one of the most beautiful landscapes in Europe. The road from Florence to Siena through Greve in Chianti, Panzano and Radda winds through vineyards and olive groves, past hilltop villages and isolated stone farmhouses, the views changing constantly and always being perfect. This is the Tuscany of the imagination — the one you see in paintings and films and on the covers of books about Italian life. It looks exactly as it does in all those pictures. It always does.
13. Garfagnana
In the far north of Tuscany, tucked between the Apennines and the Apuan Alps where the marble of Carrara is quarried, the Garfagnana is Tuscany's least visited and most surprising region. Deep river gorges, chestnut forests, medieval villages barely touched by tourism, and the extraordinary Lunigiana coast where the mountains fall directly into the sea — this is Tuscany without the crowds, and it rewards the small number of visitors who make the journey.
14. Elba
Tuscany extends to the sea, and the island of Elba — Napoleon's first exile and the largest island in the Tuscan Archipelago — is one of the finest swimming destinations in Italy. Clear turquoise water, dramatic granite cliffs, white-sand beaches hidden in coves, and hill towns with views across to the mainland. In spring and early summer, before the Italian school holidays bring the crowds, Elba is one of the most beautiful and peaceful places in Italy.
15. The Crete Senesi
South of Siena, the landscape changes. The soft green hills of the Chianti give way to something older and stranger — the Crete Senesi, a landscape of pale clay hills eroded into sharp ridges and rounded domes, almost lunar in its strangeness, scattered with cypress trees and ancient monasteries. At dawn, when the mist lies in the valleys and the light is pink and the landscape looks like a drawing by Leonardo, the Crete Senesi is one of the most beautiful and otherworldly places in all of Tuscany. Come for a morning and stay all day.
Bring Tuscany Home
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