Tuscany · Italy
The Tuscany behind the closed doors
A private, tailor-made Tuscany wine tour, built around the people who make the wine and the food. Over 5 to 7 days, you taste Brunello di Montalcino, Chianti Classico and the Super Tuscans of Bolgheri where they are made, often with the winemaker pouring.
Why we come back here
Because Tuscany keeps opening up.
The cypress roads and the Val d’Orcia are the easy part. You only have to arrive. Under the surface is where it gets interesting.
One Sangiovese grape makes different wines depending on the hill. The families behind the bottles are still here, 4 and 5 generations in.
Once you have sat at their table, they remember you for next time. First trip or fifth, we build the mix that is right for you.
The flavour of the place
Sangiovese, Chianina, olive oil, and a bread that never has salt in it.
The wine
One grape, Sangiovese, a different wine on every hill: Brunello di Montalcino, Chianti Classico, Vino Nobile, the Super Tuscans of Bolgheri.
The beef
he Chianina, the old white cattle breed behind a real bistecca alla fiorentina, grilled and dressed in nothing but olive oil.
The olive oil
Bright, green and peppery in November, rounder by March. Almost every family makes its own.
The pasta
Hand-rolled pici with a wild boar ragù, the plate that tells you which hills you are in.
Tuscany wine regions explained
One grape, a different wine on every hill.
Sangiovese runs through all of Tuscany, and it changes with every hill. Brunello di Montalcino is the serious, age-worthy one. Chianti Classico, under the black rooster, is brighter and drinks younger. Vino Nobile di Montepulciano is the structured one. And on the coast, the Super Tuscans of Bolgheri, Sassicaia and Ornellaia among them, rewrote the rules. We taste them where they are made.
The full story of each, and how they taste side by side, is on the blog.
One day, in detail
To give you the feel.
A real day from a recent Tuscany trip, built from the producers and experiences we know here.
Coffee on the terrace of the small hotel in Montalcino. The sun is still low, the valley half in fog, half in gold. Bread, fig jam, two kinds of cheese, a boiled egg. Enough to wake the body, not enough to slow it down.
The producer is waiting by the gate. He pours a Rosso di Montalcino before you have finished walking in. Forty barrels, a dog named Bruno, a window onto vines older than any of you. He talks about Sangiovese the way a farmer talks about family.
A family press, four generations at the same mill. You taste three oils side by side and understand why olive oil has vintages. Lunch under a pergola: bread, oil, pecorino with chestnut honey, pici with wild boar ragù. A glass of their wine. Then another.
Back in the car, slowly. The road climbs to a medieval village built into the hill. No ticket office, no gift shop, just a piazza where two old men play cards. Coffee at the bar. A photograph nobody asks you to take.
Dinner inside the walls of a hilltop town, eleven tables, the owner greets our guide by name. A ribollita thicker than any soup you have met, a bistecca shared between three, a panna cotta the kitchen sends out unasked. Somebody is singing above the alley.
Full sample itinerary available as a PDF.
See the full five-day sample itinerary →Who opens their doors to us here
Friends, twenty years in.
The olive oil family
in Montalcino. 4 generations at one press. The bread is from that morning, the oil is 2 weeks old.
The winemaker in Chianti
who still answers his own phone, and pours Riservas he has held back for 15 years because you are here.
The chef south of Siena
7 tables, a menu that changes by what came out of the garden that morning.
The truffle hunter
outside San Miniato, into the oak woods before light with a dog who reads the ground like a map.
The pecorino family
above Pienza, cheese aged in ash and chestnut leaves, cut at the table.
The estate that rarely opens
a name you know from restaurant lists, poured by someone from the family.
When to come
Every season is Tuscany. Some are more than others.
Spring
Late March – May
Green, quiet, wildflowers. Fava beans, artichokes, the best light of the year.
Summer
June – August
Hot and busy. We lean to Bolgheri and the coast, long lunches in the shade.
Autumn
September – early November
The best time. Harvest, turning leaves, the first white truffles. Most of our trips happen now.
Winter
Late November – February
Quiet and deeply Tuscan. Wineries have time to talk, kitchens cook heavier.
Tuscany vs Piemonte
Which one fits you better?
The 2 great wine regions of Italy ask for different moods. Our private journeys are built either way.
Tuscany
Sun, stone, and the long lunch
The feeling
Golden and generous. Warm stone, long lunches, a place that rewards slowing down and asks nothing of you but to arrive.
The wine
Sangiovese in many voices: Brunello, Chianti Classico, Vino Nobile, the Super Tuscans of Bolgheri.
The landscape
Cypress roads, the Val d’Orcia, hill towns like Montalcino and San Gimignano.
The food
Unsalted bread, ribollita, pappa al pomodoro, bistecca, pecorino, olive oil pressed that week.
Best for
First-timers to Italy, families, food lovers, and anyone who wants warmth and ease.
Piemonte
Fog, focus, and the serious glass
The feeling
Quieter and more inward. Fog on the hills till mid-morning, a seriousness that suits people who like the detail and the long conversation.
The wine
Nebbiolo at its most profound: Barolo and Barbaresco, plus Barbera and Dolcetto for the table.
The landscape
The Langhe hills, hazelnut groves, and autumn fog rolling through the vineyards.
The food
White truffle, tajarin, vitello tonnato, raw veal, and the slow richness of the cold months.
Best for
Returning wine lovers, collectors, and travellers chasing the great bottles.
Meet REAL TUSCANY
The Tuscany everyone pictures, and the one we bring you into.
Tell us about the people coming. The time of year that works. What you’re quietly hoping to come home with. We’ll come back with a shape of a trip, and we’ll refine it together until it’s yours.
A real person replies, usually the same day.
Tuscany at a glance
The shape of a trip, in short.
The shape of a trip, in short.
- Ideal trip length
- 7 days is the sweet spot, enough to do the hills properly and still add a day on the coast or in Florence. 5 at a minimum, 10 with Umbria.
- Best seasons
- late April to October. The vendemmia, in September and October, when the cellars smell of fermenting fruit, is the favourite.
- Closest airports
- Florence (FLR) and Pisa (PSA) for most of the region, Rome (FCO) for the south.
- Where you stay
- A family-run hotel inside the medieval walls, an agriturismo on a working farm, or a private villa with its own cook.
- Wine focus
- Brunello di Montalcino, Chianti Classico, Vino Nobile di Montepulciano, the Bolgheri Super Tuscans.
- Culinary focus
- new olive oil, aged pecorino, ribollita, bistecca, and white truffle in autumn. years.
- Trip style
- private and tailor-made, with insider access to producers we have known for 20 years.
- Best for
- couples marking something, old friends around one long table, collectors after cellar vintages, and food lovers who want the kitchen, not just the plat
A few things people ask
About a trip to Tuscany.
How many days do we need for Tuscany?
5 minimum, 7 is the sweet spot, 10 if you add Umbria or the coast.
What are the best months to visit Tuscany for wine?
Late April to October. September and October, the vendemmia, are the favourite. November brings the first white truffles.
What makes Brunello different from Chianti Classico?
Brunello di Montalcino is 100% Sangiovese Grosso, aged at least 2 years in oak, built to age for decades. Chianti Classico, marked by the black rooster, can carry up to 20% other grapes and drinks younger. Same grape, 2 temperaments.
What wines should we taste in Tuscany?
Brunello and Rosso di Montalcino, Chianti Classico, Vino Nobile di Montepulciano, the Bolgheri Super Tuscans, and Vernaccia di San Gimignano for a white.
Can we visit the famous names?
With the right planning, yes. Antinori, Sassicaia, Ornellaia, the great Montalcino houses. Usually 1 or 2 of them, alongside the smaller producers we have known for years. The more exclusive places need a long planning ahead.
Is Tuscany or Piemonte better for wine lovers?
Tuscany is golden and easy to love, ideal for first-timers and food lovers. Piemonte is quieter and more serious, built for collectors. Many who love one come back for the other.
Is a Tuscany wine tour worth it?
It can be as quiet or as grand as you want. What you pay for is the table you could not book yourself and the people you could not meet on your own.
Do we need to be wine experts?
No. You will know Brunello from Chianti Classico by the time you leave, because you tasted them next to each other with the person who made them.
When is truffle season in Tuscany?
White truffles around San Miniato run late October into December, November at the heart.
Are private winery visits possible?
That is the heart of what we do. Most visits are private, with the owner or winemaker, including estates that never open to the public.
Can we drive ourselves in Tuscany?
You can, the drives are short. Most guests prefer we handle it, so the winemaker can keep pouring and you can keep tasting.
When should we start planning?
5 to 7 months out. For harvest (Sept–Oct) or truffles (Nov), 8 to 9 months, the small calendars fill early.
Is Tuscany expensive?
It can be as quiet or as grand as you want. A private, tailor-made journey with insider access to producers is a real investment, and we are honest about that. What you are paying for is the table you could not book yourself and the people you could not meet on your own. We will always tell you where the money is worth spending and where it is not.
Should we combine Tuscany with Umbria?
Often, yes. Umbria sits just across the border, greener and quieter, with Sagrantino di Montefalco and a slower pulse. Ten days lets you give both room to breathe without rushing either.
What wines should we taste in Tuscany?
Brunello di Montalcino and its younger sibling Rosso di Montalcino, Chianti Classico (look for the black rooster), Vino Nobile di Montepulciano, the Super Tuscans of Bolgheri, and Vernaccia di San Gimignano if you want a white. We taste them where they are made, with the people who made them.
Are private winery visits possible?
That is the heart of what we do. Most of your visits are private, with the owner or winemaker, including estates that do not open to the public at all. It is the difference between a tasting-room flight and an afternoon in someone’s cellar.
How physical are the days?
Gentle. Some walking through vineyards and hill towns on uneven stone, an optional dawn truffle hunt in the woods, otherwise short drives and long lunches. We pace the days to you, and there is always the option to do less.
What makes Brunello different from Chianti Classico?
Brunello di Montalcino is 100% Sangiovese Grosso, serious and built to age for decades. Chianti Classico, marked by the black rooster, is brighter and more savoury, made to drink younger. Same grape, two temperaments. We taste them side by side so the difference lands in your mouth, not just on paper.
Designed by Vinspiration
Our regional expert.
Every Tuscany journey is built by hand by the two of us, from relationships with producers we have kept for two decades, not from a catalogue.
Guy Haran
Founder & CEOTwenty years building wine journeys across Italy and beyond. A Riedel ambassador and WSET-trained wine educator, author of the book Wine Journey and host of the Wine is Basic podcast. The friendships that open the cellar doors in Montalcino, Chianti, and Bolgheri are his, built one harvest at a time.
Fabio Masini
italy expertOur man on the ground across central and northern Italy. Fabio is a wine person to the core, with the knowledge in his blood, but what moves him is showing people his own country, down to its quietest cultural details. On many trips, Fabio is the one who guides you himself, through streets he has known since childhood.