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SIENA & THE CRETE SENESI

The Medieval City and the Clay Desert

A city frozen in the thirteenth century, and pale hills to the south that look like the end of the world.

Siena lost the Renaissance and never recovered. Florence won — politically, commercially, culturally — and Siena was left behind, frozen somewhere in the thirteenth century, preserved by its own defeat. This turns out to have been extraordinarily fortunate. While Florence was busy becoming a modern city, Siena stayed medieval. The Piazza del Campo is still the most beautiful public square in Italy. The Palio still runs twice a year with a violence and pageantry that hasn't changed in four centuries. The city still divides itself into seventeen contrade — neighbourhoods with their own flags, churches, and loyalties — and takes the whole thing completely seriously.


The Crete Senesi begins south of the city where the vineyards end and something stranger takes over. Pale clay hills, deeply eroded, almost lunar in the midday light. Isolated farmhouses. Abbeys that appear without warning on hilltops. The landscape looks post-apocalyptic and achingly beautiful at the same time.


Most visitors see Siena in a day trip from Florence. They see the piazza, the cathedral, and the queue for the museum. They miss everything else. Give it two nights minimum and walk into the contrade after dark when the city belongs to itself again.

WHEN TO COME

May and September. The Palio runs July 2nd and August 16th — extraordinary to witness, impossible to find a room. Come the week before or after if you want the atmosphere without the chaos.

HOW TO MOVE

Siena on foot — the city is steep and entirely walkable. The Crete Senesi by car, on the white gravel roads that connect the abbeys and farms. Monte Oliveto Maggiore is worth the detour.

WHO IT'S FOR

Anyone who finds Florence too busy and too famous. Siena rewards the curious and punishes the rushed. The Crete Senesi is for photographers, painters, and people who don't mind being alone with something beautiful."

WHERE TO STAY

Siena & the Crete Senesi's Finest

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Castel Monastero

Castelnuovo Berardenga, Siena

"A medieval village, privatised and perfected. The Contrada restaurant just got its first Michelin star. The timing is good."

A restored 10th-century medieval hamlet in the Chianti hills — with a Michelin-starred restaurant and a glorious spa.

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Certosa di Maggiano

Siena, Tuscany

"The monks chose this hillside for silence and beauty. Both are still very much in evidence."

A 14th-century Carthusian monastery one kilometre outside Siena — Relais & Châteaux, Renzo Mongiardino interiors, fifteen rooms, and the particular quiet of a building designed for exactly this kind of stillness.

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Grand Hotel Continental Siena

Siena, Tuscany

"Pope Alexander VII built this palazzo as a wedding gift. The bride was fortunate. So are you."

A 17th-century papal palazzo three minutes from the Piazza del Campo — frescoed ceilings, a wine cellar carved into a medieval tower, and the only five-star address inside Siena's walls.

SIENA & THE CRETE SENESI EXPERIENCES

Go Deeper

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WINE & FOOD TOUR

Truffle Hunting in the Crete Senesi

Follow Alessandro and his dog Moka through the Crete Senesi woods, hunt for truffles, then taste the spoils at his shop in central Siena. One hundred and sixteen reviews. Not one of them regrets it.

Best For: 

Duration:

Foodies · Curious Travellers

2.5 hours

"Siena lost to Florence five centuries ago. Looking at it now, you have to wonder who really won."

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