Can I rent a villa in Siena itself?

Not from us. We keep our villas in the countryside; the closest sit about forty minutes south at Castiglion del Bosco, and Siena works best as the big day out of the week.

Twice each summer, on 2 July and 16 August. Standing in the Campo is free; balcony seats book out months ahead and we can arrange them for guests who plan early.

How far is Siena from the collection's villas?

About forty minutes from Castiglion del Bosco and under an hour from most of the southern villas; the Chianti and Lucca villas are further.

Is Siena better than Florence for a day trip?

Different: Siena is medieval, compact and walkable in a day; Florence is the Renaissance and needs two. From a southern villa base, Siena is the easier and often the more loved of the two.

Exclusive Tuscany

Est. MMXXV

TuscanySub-region

Siena, Tuscany.

The medieval city ringed by the best of Tuscany — Chianti to the north, the Crete Senesi to the south-east, the Val d'Orcia beyond.

1 villa in the collection1 piece in the journal

Villas in Siena

The whole collection

Countryside Classic01

Villa Elle

Siena · 24 guests · 12 bedrooms

From €13,503 / week

View villa

On Siena

Siena,
from Smaranda.

Siena is the city the south of Tuscany answers to: banking rival to Florence until the plague of 1348 froze it, which is precisely why the medieval city survives so completely. The scallop-shaped Campo, the striped Duomo, the seventeen contrade whose flags hang in every alley, none of it is staged for visitors; the Palio is run for the city itself, twice each summer, and the tourists watch from the edges.

We keep no villas inside Siena, deliberately. A villa week wants country around it, and Siena is a city you visit rather than sleep in: park below the walls, walk up for the morning market and the Duomo, take the long lunch, and be back at the pool by four. The closest villas in the collection sit forty minutes south at Castiglion del Bosco, which makes Siena the natural big day out of a Val d'Orcia or Crete Senesi week.

The Palio, Honestly

The Palio runs on 2 July and 16 August, and the days around each are the only time Siena feels crowded to its bones. Standing in the Campo is free, packed and hot; balcony and window seats are bookable months ahead at serious prices, and we arrange them for guests who plan early. If pageantry without the crush appeals more, the trial races on the preceding days give most of the spectacle with a fraction of the crowd.

A Day in Siena from a Villa

Siena is a ZTL city: leave the car in the Santa Caterina or Il Campo garages below the walls and take the escalators up. The rhythm that works: the Campo before ten, the Duomo and its striped nave mid-morning, lunch in a contrada osteria away from the square, then the Pinacoteca or Santa Maria della Scala if the afternoon stays cool. From Castiglion del Bosco the drive is about forty minutes each way, which leaves the evening at the villa intact.

When to come

April to June and September to October for city walking weather. The Palio makes early July and mid-August electric but crowded; winter Siena is quiet, cold and entirely itself.

Towns worth knowing

Monteriggioni: The ring of walls Dante used as a simile for the abyss; twenty minutes north, an hour is enough.
Sovicille: West of the city, quiet Romanesque pievi and the Montagnola woods.
Murlo: Tiny Etruscan hilltop borgo with a serious small museum.
Buonconvento: Walled and flat, on the road south toward the Val d'Orcia villas.

Best for

The grandest single day trip of a southern-Tuscany week
Art and architecture without Florence's queues
The Palio, planned properly
Pairing with a Val d'Orcia or Crete Senesi villa base

Plan your stay

To choose a countryside base for city visits, compare villas near Siena. Our Siena day guide helps you plan an outing without trying to fit the whole province into one day.

Practicalities

Siena is forty minutes from the Castiglion del Bosco villas and under an hour from most of the southern collection. Park below the walls (ZTL applies inside) and walk up; the escalators from the Santa Caterina garage do the climbing.

Frequently asked

Can I rent a villa in Siena itself?: Not from us. We keep our villas in the countryside; the closest sit about forty minutes south at Castiglion del Bosco, and Siena works best as the big day out of the week.
When is the Palio?: Twice each summer, on 2 July and 16 August. Standing in the Campo is free; balcony seats book out months ahead and we can arrange them for guests who plan early.
How far is Siena from the collection's villas?: About forty minutes from Castiglion del Bosco and under an hour from most of the southern villas; the Chianti and Lucca villas are further.
Is Siena better than Florence for a day trip?: Different: Siena is medieval, compact and walkable in a day; Florence is the Renaissance and needs two. From a southern villa base, Siena is the easier and often the more loved of the two.