HV10667
Impruneta
Florence Countryside and Chianti
Weddings 2027
A Renaissance hamlet, all yours
The Hidden Voyage guide
Siena and Val d'Orcia
The UNESCO valley of cypress roads, Brunello and Renaissance villages.
Best months
May, Jun, Sep, Oct
Ideal stay
7 nights
Fly into
FLR · PEG · PSA · FCO · BLQ
Getting around
Car essential; driver for wine days
Our villas here
41 private villas
Why go
Why choose Siena and Val d'Orcia
Southern Tuscany offers two of Italy's great treasures within an hour of each other. Siena is a Gothic city of brick palaces and steep lanes gathered around Piazza del Campo, while the Val d'Orcia unfolds in gentle hills, lone cypresses and Renaissance towns that UNESCO recognises as a model landscape. Add Brunello and Vino Nobile cellars, and the case for a villa here is compelling.
The region suits travellers who enjoy beauty at a measured pace: photographers chasing dawn light over the hills, wine lovers touring Montalcino and Montepulciano, couples seeking thermal springs and families who want space. Days unfold slowly, with lunch in a hilltop piazza and sunsets that colour the whole valley.
Ideal for: Wine lovers, Weddings, Photography and slow travel · Slow, scenic and gastronomic
Our villas of the month · October 2026
Chosen this month by our team
HV255
Bibbiano
Siena and Val d'Orcia
Our pick in Siena and Val d'Orcia
HV1651263776
Sant'Angelo in Colle
Siena and Val d'Orcia
Our pick in Siena and Val d'Orcia
Getting there
Airports and arrivals
FLR
Florence Airport (Amerigo Vespucci, Peretola)
about 1h15 by car to Siena, about 2h to Pienza
closest airport to Siena
PEG
Perugia San Francesco d'Assisi
about 1h15 by car to Montepulciano
small Umbrian airport, convenient for the southern Val d'Orcia
PSA
Pisa International (Galileo Galilei)
about 1h45 by car to Siena
wide choice of European routes
FCO
Rome Fiumicino (Leonardo da Vinci)
about 2h30 by car to Pienza
best for intercontinental flights to the southern valley
BLQ
Bologna Guglielmo Marconi
about 2h15 by car to Siena
alternative for long haul connections
- Trains from Florence reach Siena in about 1h30 with a change at Empoli; regular express buses take about 1h15 to the city centre.
- Chiusi Chianciano Terme station, on the line between Florence and Rome, is about 25 minutes by car from Montepulciano.
- By car, the A1 motorway exits at Chiusi Chianciano Terme or Valdichiana serve Montepulciano and Pienza, while the SR2 Via Cassia crosses the Val d'Orcia.
- Private transfers and helicopter flights to licensed sites can be arranged for faster connections from Rome or Florence.
We arrange private transfers, drivers, boats and helicopters for every villa.
Where to stay
Choosing your base
Siena
Culture lovers, short stays
A city of contrade, Gothic palaces and pedestrian lanes, best for those who want culture and restaurants at the door.
Pienza
Couples, photographers
The ideal Renaissance town planned by Pope Pius II, perched above the Val d'Orcia with views from its walls.
Montalcino
Wine enthusiasts
A fortified hilltown entirely devoted to Brunello, surrounded by some of Italy's most prestigious estates.
Montepulciano
Families, wine and food
A long, steep Renaissance town with grand palazzi and cellars carved deep into the hill.
San Quirico d'Orcia and Bagno Vignoni
Wellness, touring the valley
A central, low key base close to the thermal square of Bagno Vignoni and the most photographed hills.
Crete Senesi
Privacy, longer stays
Bare, clay hills between Siena and the Val d'Orcia, almost lunar in summer and remarkably peaceful.
Positions are approximate: the exact address is shared once your stay is confirmed.
What to see
The highlights
01
Piazza del Campo and Torre del Mangia, Siena
The fan shaped square slopes down to the Palazzo Pubblico, where Lorenzetti's frescoes of Good and Bad Government fill an upper hall. Climb the tower for a sweeping view over rooftops and countryside.
02
Siena Cathedral
Striped marble, a pulpit by Nicola Pisano and the Piccolomini Library frescoed by Pinturicchio make this one of Italy's great churches. The inlaid marble floor is uncovered only for limited periods each year.
03
Pienza
Rebuilt in the fifteenth century as an ideal town, Pienza was inscribed by UNESCO in 1996. Walk the panoramic lane along its southern walls at sunset.
04
Val d'Orcia landscape
Recognised by UNESCO in 2004, the valley's rolling wheat fields and cypress lined roads inspired Renaissance painters. The Cappella della Madonna di Vitaleta near San Quirico is its best known postcard.
05
Bagno Vignoni
A hamlet whose main square is a great stone basin of steaming thermal water. Bathing in it is not allowed, but nearby spas and the free pools below the village are open to all.
06
Abbey of Sant'Antimo
A luminous Romanesque abbey in a valley below Montalcino, built of travertine and alabaster. Its setting among olive groves is unforgettable at dusk.
07
Montepulciano Piazza Grande
Crowned by the Palazzo Comunale and the cathedral, the square sits at the highest point of town. Beneath the surrounding palaces lie historic wine cellars open for tastings.
08
Abbey of Monte Oliveto Maggiore
A Benedictine monastery in the Crete Senesi with a cloister frescoed by Luca Signorelli and Sodoma with scenes of Saint Benedict's life.
What to do
Experiences worth planning for
Brunello estate tour
Visit cellars around Montalcino and taste Brunello alongside Rosso di Montalcino, guided by a sommelier or the producers themselves.
Thermal day
Spend a morning in the warm waters of Bagno Vignoni or the natural white limestone pools of Bagni San Filippo.
Pecorino tasting in Pienza
Meet cheesemakers and taste pecorino at different ages, from fresh and milky to aged in ash or walnut leaves.
Photography at sunrise
Follow a local photographer to the classic viewpoints as mist settles in the valleys at dawn.
Vintage car or e bike through the Val d'Orcia
Explore the white roads between Pienza, Montichiello and San Quirico at your own rhythm.
White truffle hunt in the Crete Senesi
In autumn, follow a trufflehunter and his dog through the woods around San Giovanni d'Asso.
Outdoors
Nature and walks
Bagni San Filippo
Free natural thermal pools and a vast white calcareous formation known as the White Whale.
Bagno Vignoni pools
Warm water cascades into open air pools in the old mill park below the village.
Monte Amiata
An extinct volcano rising to 1,738 metres, with beech forests for summer walks and snow in winter.
Via Francigena, San Quirico to Radicofani
A stretch of the ancient pilgrim route crossing the valley's most open landscapes.
Riserva Naturale di Lucciolabella
A protected area of eroded clay badlands near Pienza, home to unusual flora and birdlife.
Where to stay
Private villas in Siena and Val d'Orcia
HV255
Bibbiano
Siena and Val d'Orcia
HV1651263776
Sant'Angelo in Colle
Siena and Val d'Orcia
HV1768924525
Sovicille
Siena and Val d'Orcia
HV10712
Sarteano
Siena and Val d'Orcia
HV10201
Sarteano
Siena and Val d'Orcia
HV1557152195
Buonconvento
Siena and Val d'Orcia
HV1605885723
Montalcino
Siena and Val d'Orcia
HV1708344334
Buonconvento
Siena and Val d'Orcia
At the table
Food and wine
What to eat
Pici
Thick hand rolled pasta, served with garlicky tomato sauce or simply with breadcrumbs.
Pecorino di Pienza
Sheep's cheese from the Val d'Orcia pastures, sold in every shade of maturity.
Panforte
Siena's dense, spiced cake of honey, almonds and candied fruit, a medieval recipe.
Ricciarelli
Soft, crackled almond biscuits dusted with icing sugar, a Sienese speciality.
Cinta Senese
Free range native pork, made into prized salumi and slow roasts.
Crete Senesi white truffle
The rare tartufo bianco found in the clay hills in autumn, shaved over fresh pasta and eggs.
What to drink
Brunello di Montalcino DOCG
A deep, long lived pure Sangiovese, released only after extended ageing.
Vino Nobile di Montepulciano DOCG
A refined Sangiovese red from the slopes around Montepulciano, aged in cellars beneath the town.
Rosso di Montalcino DOC
The younger, fresher sibling of Brunello, approachable from early on.
Orcia DOC
A small appellation of Sangiovese based wines from the valley itself, often from boutique producers.
Beyond the villa
Day trips
Florence
about 1h15 by car from Siena
The Renaissance capital, easily combined with a stay in Siena.
Chianti Classico
about 40 minutes by car from Siena to Castellina
Wine estates and medieval villages on the road north.
Cortona
about 45 minutes by car from Montepulciano
An Etruscan hilltown above the Val di Chiana.
Orvieto
about 1h by car from Pienza
A dramatic Umbrian city on a tufa cliff with a dazzling cathedral facade.
Lake Trasimeno
about 45 minutes by car from Montepulciano
A wide, tranquil lake with islands and lakeside villages in Umbria.
When to go
The year, season by season
May to June and September to October, with the harvest in autumn. Summer is hot and dry.
Spring
Green wheat fields and poppies make April and May the most photogenic months. Temperatures are mild and the roads quiet.
Summer
The hills turn gold after the harvest of the wheat in June, and evenings are made for dinners outdoors. Days can be very hot, so a villa with a pool is precious.
Autumn
Vineyards glow, the grape harvest is under way and truffle season begins. September and October are among the most rewarding months.
Winter
Quiet, crisp and often misty, with thermal baths at their most inviting. Some country restaurants close between January and March.
Weather month by month
Bars: hours of sunshine a day. Above: average daytime high. Shaded: the best months.
Full weather table
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Daytime high, °C | 11 | 13 | 16 | 20 | 24 | 29 | 32 | 32 | 27 | 22 | 16 | 11 |
| Night low, °C | 2 | 3 | 5 | 8 | 12 | 16 | 18 | 19 | 15 | 11 | 6 | 3 |
| Sunshine, hours a day | 3 | 4 | 5 | 6 | 8 | 9 | 10 | 9 | 7 | 5 | 3 | 3 |
| Rainy days | 8 | 7 | 7 | 9 | 8 | 5 | 3 | 4 | 6 | 9 | 10 | 10 |
| Dry days | 24 | 21 | 24 | 21 | 23 | 25 | 28 | 27 | 24 | 22 | 20 | 21 |
Air: averages 1991 to 2020, Florence Peretola weather station. Dry days have less than 1 mm of rain.
Events through the year
2 July and 16 August
Palio di Siena
Ten contrade race bareback around Piazza del Campo in three thrilling laps, after days of rituals, trials and processions.
Last Sunday in August
Bravio delle Botti, Montepulciano
Teams from the town's districts push heavy wine barrels uphill through the streets to Piazza Grande.
First Sunday in September
Fiera del Cacio, Pienza
A celebration of pecorino with tastings and the traditional cheese rolling game in the main square.
Last weekend in October
Sagra del Tordo, Montalcino
Archery contests between the town's quarters, costumed parades and harvest feasting.
November
White truffle fair, San Giovanni d'Asso
A market and tastings dedicated to the white truffle of the Crete Senesi.
Planning Siena and Val d'Orcia?
Tell us your dates and the group: we reply with availability and the full price, usually within one working day, and arrange transfers, chefs and boats.
Good to know
Practical tips
- Siena's centre is a limited traffic zone; park at the Santa Caterina or Il Fagiolone car parks, which have escalators up into the city.
- For the Palio, the square fills hours before the race; a reserved balcony or terrace seat is the most comfortable way to watch and sells out months ahead.
- Wineries in Montalcino and Montepulciano usually require booking, and Sunday visits can be limited.
- Bathing in the main square pool of Bagno Vignoni is not permitted; use the spa or the free pools below the village.
- Petrol stations and cash machines are sparse in the countryside, so refuel and withdraw cash in larger towns.
- Siena and several Val d'Orcia towns apply a municipal tourist tax per person per night, collected by the property.
Questions
Siena and Val d'Orcia: frequently asked
Is it better to stay in Siena or in the Val d'Orcia?
Siena is ideal for a few nights of city culture, while the Val d'Orcia offers space, views and wine country. Many guests combine a villa in the valley with day trips into Siena, about an hour away.
When is the Palio di Siena?
It is held twice a year, on 2 July and 16 August, in Piazza del Campo. Trials and processions take place in the days leading up to each race.
What is the closest airport to the Val d'Orcia?
Perugia (PEG) is about 1h15 from Montepulciano and Florence (FLR) about 2h from Pienza. Rome Fiumicino (FCO) is around 2h30 away and offers the most international connections.
Is the Val d'Orcia a UNESCO site?
Yes, it was inscribed in 2004 as a cultural landscape. Pienza's historic centre and Siena's historic centre are separate UNESCO sites.
How many days do you need in the Val d'Orcia?
A week allows unhurried visits to Pienza, Montalcino, Montepulciano and Bagno Vignoni, plus a day in Siena. Three or four days covers the essentials.
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