You know how it usually goes.
Someone in your circle went to Italy last spring. The photographs were beautiful. What the photographs left out was the forty minutes on hold with the front desk, the driver who missed the turn twice, the waiter who smiled and understood nothing, the dinner where they translated the menu to each other while it went cold. They came home with a phone full of pictures, and with a feeling nobody says out loud: all that money, and Italy never really let them in.
The ones who joined an organized group had it worse. They paid a great deal to spend eight days on somebody else’s schedule, at a long table of strangers, in a country whose language none of them spoke.
Money did not fix either one. Money bought the best room in the best hotel and left them standing on the wrong side of the door.
And on every one of those trips, somebody was still working. Somebody watched the transfers and solved each small failure as it came. If your family is like most, that somebody is you.
The three Tuscanies
The one every visitor gets
The queue at the Duomo, the restaurant your concierge can book because anyone’s concierge can book it. It is beautiful, and it is the same for everyone. You can spend a fortune there and still see only what the crowds see.
The comfortable one
The right hotels, the right beaches, people of your own world at the next table. It is restful, and it is never a mistake. But it is still a holiday you build yourself, from the first booking to the last transfer, and when something goes wrong it is yours to fix, in Italian or through a translator. You pay for rest, and you keep the job.
The one almost never offered
The real Tuscany, its working cellars and its family tables, received in your own language, with only your own people beside you and nothing for you to arrange. It is not for sale on any website. Here, doors open to faces they know, or they do not open at all.
The man
Twenty-five years ago Sergey left Russia for Italy and began the slowest kind of work: not to see the country, but to be let into it. He learned the language until the accent was gone. He spent years earning what no hotel can hand you: the private number of the winemaker who takes no visitors, the family that opens its gate for him and for no one else. It was more than a decade before he received his first guests.
Now he is the rarest thing this country offers a Russian family: one of your own, on the inside. For eight days he stands between you and every word of Italian, every arrangement, every difficulty: he settles them in Italian, and brings them back to you in Russian, so that you never have to. He does not hand you a schedule and leave you to it. He opens a country, and walks you in.
He is not a guide. He is the door, and he is one of yours.
Who sits at your table
Every other way of doing this puts you with people a company chose: a group assembled from a booking sheet, a long table of faces you will smile at and forget. That is fine, at a certain level. At yours, it is not. You have learned to be careful about who you are surrounded by, and eight days is a long time to be careful.
So these days are only ever your own. Your family, or the few friends you would actually choose. Two to six people, once. The road, the table, the house in the evening: yours alone, and no one else’s. Who you spend these days with is not a detail we manage. It is the one thing we will not touch.
Your own people only
Two to six guests
Not one stranger
The eight days
Picture them not as a schedule but as the things you will describe to people whose attention is hard to hold.
The first evening: dinner under a sixteenth-century loggia above Florence, one of eight tables in the room, the city going gold below Brunelleschi’s dome. The welcome is in Russian, and so is the whole evening.
The first evening · Villa San Michele
One lunch is laid inside a working family winery in the Vernaccia country outside San Gimignano, between the cellar and its own vines, and the wine is poured by the people who grew it. Not a tasting room with a script: a family table that happens to stand among barrels.
Day three · The Vernaccia country
A morning on a white road through hills of grey clay that look like a slow sea. The road is empty, and it is yours: on foot, on a bicycle if you want one, or from the back seat with the windows down and someone else driving.
Day five · The Crete Senesi
The last nights in a medieval village that had been left to ruin and was brought back one stone house at a time. The hotel is the village itself, and its guests are counted in handfuls.
The last three nights · Monteverdi, Val d’Orcia
You will not read a menu you cannot follow, wait for a car that does not come, or explain yourself to anyone. Everything that would normally be yours to manage is quietly Sergey's. What is left for you is the part everyone is promised and almost no one is given: to be present, in your own language, among your own people, with nothing to arrange.
Florence from above
You are received at Villa San Michele, a monastery from the early fifteenth century with a facade attributed to Michelangelo. Dinner on the loggia as Florence lights up below. If you land early, the city first: the Duomo, the Signoria, the Ponte Vecchio at dusk, with one of your own beside you.
The hills at your pace
Quiet roads north of Fiesole, olive terraces, no traffic. Ride as far as you like or not at all; the car is always a turn behind. Lunch in a hillside trattoria that keeps no menu for strangers.
Day three
A hill of flight and a castle
A morning on Monte Ceceri, where in 1506 Leonardo tried to make a man fly. Then the towers of San Gimignano and a long lunch over a glass of Vernaccia. In the afternoon, the private estate of Castello di Casole, a tenth-century castle on four thousand acres that once belonged to Luchino Visconti.
Siena
The shell of the Piazza del Campo, the striped cathedral, the streets of the contrade that race one another twice a year, shown privately, in your own language. Lunch at a table the groups do not reach. The afternoon is yours: the spa cut into the old wine cellars, the pool, or the hills.
The lunar hills
The Crete Senesi: bare clay hills like a slow sea, single farmhouses crowned with cypress, white roads that lead to no one. By bicycle or by car. In the late afternoon the road climbs to Monteverdi, and the Val d’Orcia opens below.
Slow
A day without a clock. The cypresses of La Foce and the garden Iris Origo made from bare land, the road you have seen a thousand times without knowing where it was. Or Pienza. Or simply the pool and the valley and the quiet.
The long day if you want it
For those who ride, the finest day: Sarteano and Cetona on their hills, the avenue of cypresses, a fortress on the far horizon. For those who do not, the same country at rest. A last dinner to close the week.
The road to Rome
A slow morning, a last coffee in the village, the private road to Rome, perhaps a pause beneath the cathedral of Orvieto on its cliff. You leave with the album to come.
Everything, taken care of
The houses
Seven nights across three houses, Fiesole to the Val d’Orcia, chosen and arranged long before you land.
The road
Every private transfer, Rome to Rome. Bicycles fitted to you, and a support van for any day you want the road.
Sergey
With you for all eight days. Doors opened in person, and a table arranged where none was free.
The table
Every meal along the way is taken care of, from the welcome dinner above Florence to the last coffee before Rome.
The album
A photographer travels the whole way, quietly. A hand-bound album follows you home.
Yours to arrange
Your flights. Nothing else.
The three houses
Nights 1 and 2 · Belmond · Fiesole
Villa San Michele
A monastery from the early fifteenth century above Florence, its facade attributed to Michelangelo. Dinner on the loggia as the city goes gold below.
Nights 3 and 4 · Belmond · Val d’Elsa
Castello di Casole
A tenth-century castle on four thousand acres that once belonged to Luchino Visconti. The spa is cut into the old wine cellars.
Nights 5 to 7 · Val d’Orcia
Monteverdi
A medieval village brought back one stone house at a time. The hotel is the village itself, and its guests are counted in handfuls.
From past seasons
Sergey has received Russian-speaking guests across Italy for more than a decade. What follows is what they say when the week is over, translated from the Russian.
“The organization is thought through to the last detail: for the whole journey you feel light, and looked after. The team helps with everything.”
“Everything simply worked, without a single question. Beautiful beyond words, comfortable, and quietly inspiring in a way you feel the entire time.”
What you carry home
You will not come home with photographs on a phone. A photographer travels the whole way. Some weeks later a hand-bound album arrives at your door: eight days no one else will ever have, in a form you can hold, set on a table, and open in front of the people you most want to tell.
If you have been disappointed before
If you have been disappointed by expensive things before, you are exactly who this was built for. So here it is, plainly.
This is slow. In eight days you will see one small corner of Tuscany, at the pace of a long lunch. If you want to see all of Italy at once, you will be frustrated, and you should go with someone else. For these eight days you also give up the wheel. Not the choosing: any morning can become a pool and a closed gate, decided over breakfast, and nothing on the programme is ever an obligation. What you hand over is the managing, and most people cannot hand over even that.
What you get for giving up control is the only thing worth giving it up for. You stop managing, entirely. This spring a private Russian family travelled this Tuscany with Sergey. Their week is the reason this page exists. And if anything ever falls short of what was promised, he settles it himself, that day, at our cost. You are never left to sort out Italy alone. That is the whole point of him.
Who this is not for
This is a small thing, built for a particular kind of family. So it is easier to say who it is not for.
If what you want from Italy is a good hotel, a good driver and a long list of sights, you do not need Sergey: any agency will arrange that, for far less. If a week only feels well spent when you have crossed five cities off a list, these days will feel slow to you by the second morning. And if the cost of eight private days is a number you would need to think about, this was built for someone else, and Sergey would tell you so kindly, because pretending otherwise would waste your time and his.
It is for the ones who built everything themselves and have never once been off duty. Who stopped collecting places years ago, and want something rarer now: to arrive in a country and be expected there. You are allowed to want one week where nothing needs you. You earned it a long time ago.
The measure of it
He receives a small number of families each season, from two to six guests at a time, once. He cannot be in two valleys at once, and he does not try. When a season is taken, it is taken, and the people in it are the only ones who will ever have those particular eight days.
guests, no one else
days no one else will have
Two departures remain this year · never more than five
The price
This is not a sales trick. The price depends on who is travelling, when, and in which houses, so a number printed here would mean nothing. Sergey tells it to you himself, on the phone, in Russian, once. And if you need to see a price before you know whether this is for you, then it is not for you, and it is kinder to say so now.
(It is a large number. Nobody will defend it to you, and you would not respect it if they did.)
The invitation
Tell us who is travelling, and when. That is all this page asks of you. If the season is open and it is right, Sergey calls you himself, in Russian, and the two of you decide together whether these are your eight days. There is nothing to book here, and nothing to book in a hurry. There is only a door, and a man who chooses who he opens it for.
The families who take these days decide the way they decide most things: quickly, and once.