One estate, five nights, and a landscape that was designed — by farmers, five centuries ago.
The Val d’Orcia looks composed because it was: every cypress line and wheat curve placed by hands that thought in generations. This sketch borrows that patience. You unpack once, at a wine estate south of Siena, and let the days radiate outward — Brunello cellars, Pienza’s pecorino caves, a thermal pool the Romans found first.
Dinners matter here more than anywhere: at the winemaker’s own table, under a pergola, in a borgo kitchen. Come in September and the harvest happens around you; come in May and the hills are impossibly green. Either way, bring loose trousers.
5
Nights on the estate
10
Private doors opened
48h
To your first proposal
This is a sketch, not a package. Dates, pace, houses and tables all bend around who’s travelling — no two versions of this journey have ever left the studio the same.
02Day by day
Day 1 · Arrival
The road does the introductions.
South from Florence or Rome, the autostrada gives way to white roads and the first cypress avenues. The estate’s gates close behind you: suite in the old granary, walk through the vines before dinner, and a first glass of what the ground under your feet can do.
Estate check-in — vines on three sides, silence on the fourth
Cellar-door welcome — the house wine, at the house
Val d’Orcia, first light
Day 2 · Montalcino
Brunello, from the ground up.
A day inside the appellation: two estates, opposite philosophies — one all steel and precision, one still thinking in decades under cobwebbed vaults. Barrel tastings with the people who made them, then a long lunch in the vines where the bottles keep arriving until someone surrenders.
Two cellars, two schools — modernist and traditionalist
Barrel tasting of vintages that aren’t born yet
The long lunch — three hours, five bottles, no verdict
Brunello, underground
Day 3 · Pienza & the springs
Cheese caves, then hot water.
Pienza — the perfect Renaissance town, pocket-sized — for pecorino aged in tuff caves and a walk out to Monticchiello between the hedgerows. As the light goes low, you sink into a thermal pool that has been easing backs since Roman legions marched this road. Dinner is late and short-distance.
Pecorino in the caves — five ages, tasted at the source
The Monticchiello walk — the postcard, on foot
Thermal evening — steam rising into cypress silhouettes
Pienza, five ages deep
Day 4 · Siena & Chianti
The city of the Palio, then the backroads.
Siena early, before the buses: the Campo at coffee hour, the Duomo’s striped nave, a contrada museum opened just for you — the Palio explained by someone who has ridden in it. Home the long way through Chianti’s gravel roads, stopping only where the signs are hand-painted. Tonight: dinner at the winemaker’s table.
Contrada doors opened — banners, silks, and grudges
Chianti gravel roads — the wine country GPS ignores
The winemaker’s table — family recipes, library bottles
Chianti, the road home
Day 5 · Farewell
Saddle, truffle, or nothing at all.
The last day bends to you: horseback through the vines at dawn, a truffle hunt with a dog who outranks everyone, or simply the pool and a book. At sunset, one final table under the pergola — olive oil from the trees you can see, wine from the rows behind you, and the hills doing their slow gold thing.
Dawn ride or truffle hunt — choose your Tuscany
Farewell under the pergola — everything from within sight
Through the vines, at dawn
03Moments
The frames you’ll keep.
Travel sideways
The rowsGeometry you can drink.The huntBlack gold, dug at dawn.The glassTo the vintage.The groveTrees older than the recipes.
04Where you’ll sleep
An estate that makes things.
The classic · Val d’Orcia
A working wine estate
Suites in the old granary, a pool looking at Monte Amiata, and a cellar downstairs that smells of patience.
The alternative · a borgo
A restored hamlet, whole
For families and small groups: a village of your own — houses round a piazza, one long table, staff who appear and vanish.
Houses are named in your proposal — we hold allocations at a handful of properties we know room by room.
05In good hands
Door to door
Private driver throughout — the white roads and the wine both argue against self-driving.
Hosts, not guides
Winemakers, a cheese ager, a contrada veteran, a truffle dog’s human — people we’d invite to dinner.
Tables & tastings
Every cellar, cave and pergola table booked and sequenced — including the ones without signs.
In-trip concierge
One WhatsApp thread, answered by a person in Rome, for anything — from a case shipped home to a fourth seat at dinner.
One contact
A single itinerary designer from first sketch to the flight home — no handovers, no call centres.
Cellar logistics
Everything you fall for is shipped, insured, door to door — suitcases stay for clothes.
06Make it yours
Start from this sketch.
Tell us who’s travelling and what you’d change. A first, itemized proposal comes back within 48 hours — built once, for you.
