The icons, done right · Private day trips from Florence

Tuscan Classics: the famous places, the way locals see them

Chianti, San Gimignano, Siena, Montalcino, Montepulciano, Bolgheri and the truffle woods of San Miniato. The names everyone knows, visited with family winemakers, at quiet hours and around a long table, never from a tour bus.

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01Chianti Hidden GemsFamily cellars & lunch in the barrels 02San Gimignano & SienaTowers, Vernaccia & the Campo 03MontalcinoBrunello country 04Nobile di MontepulcianoCellars under a Renaissance town 05BolgheriThe Super Tuscan coast 06Truffle Hunting & BubblesA real hunt above San Miniato

01 · Chianti Classico · about 40 min from Florence

Chianti wine tour from Florence: family estates off the tour-bus roads

Between Florence and Siena, the white roads of Chianti Classico lead to small organic estates where the winemaker pours the wine himself.

We skip the famous names and take you to multigenerational family cellars: a walk in the vines, a look at the barrels, and a long lunch served among them with handmade pasta and the estate's wines. Two estates on the half day, three on the full day.

Why it's a classic Real families, not visitor centres, and lunch is the tasting.

⏱️ 4–8 hours
🍷 2 or 3 family estates
🍝 Lunch in the cellar
💶 From €220 / person, group of 8 · €350 for 2

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02 · San Gimignano & Siena · about 1 hour from Florence

San Gimignano and Siena in one day from Florence, with a Vernaccia lunch

The medieval towers of San Gimignano in the morning light, Siena's shell-shaped Piazza del Campo in the afternoon.

In between, a quiet family estate pours Vernaccia di San Gimignano, Tuscany's historic white wine, with a long lunch among the vines. We time the towns to miss the crowds of the coaches, and leave you free to wander.

Why it's a classic Two of Tuscany's great towns, with a family table in between.

⏱️ 9 hours
🏰 Two UNESCO towns
🍷 Vernaccia & lunch
💶 From €220 / person, group of 8 · €350 for 2

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The estate cat on a vineyard terrace below a hilltop village near Montalcino

03 · Montalcino · about 1h45 from Florence

Brunello di Montalcino wine tour: two estates and a hilltop town

High above the Val d'Orcia, Montalcino is the home of Brunello, one of Italy's greatest red wines.

Two estates, two readings of Sangiovese: Rosso and Brunello di Montalcino tasted with the families who make them, lunch among the vines, and free time in the town's piazza and fortress.

Why it's a classic The king of Tuscan reds, tasted where it is born.

⏱️ 8 hours
🍷 Two Brunello estates
🏰 Town & fortress
💶 From €250 / person, group of 8 · €400 for 2

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04 · Montepulciano · about 1h30 from Florence

Vino Nobile di Montepulciano: two family cellars and the hill town

Montepulciano sits on a ridge of the southern Tuscan hills, its cellars dug deep beneath the Renaissance palaces.

Two family-run cellars, each with its own reading of Vino Nobile, then an afternoon in the hill town with views across the Val d'Orcia and Valdichiana.

Why it's a classic One of Tuscany's oldest wines, with far fewer visitors than Chianti.

⏱️ about 8 hours
🍷 Two family cellars
🌄 Val d'Orcia views
💶 From €230 / person, group of 8 · €380 for 2

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The castle and village of Bolgheri from above

05 · Bolgheri · about 1h45 from Florence

Bolgheri Super Tuscan wine tour: cypress roads to the coast

Down the five kilometres of the Viale dei Cipressi, the Tuscan coast is home to the Super Tuscans.

You choose three stops among icon estates and boutique producers, with lunch at Enoteca San Guido if you wish, and the castle gate of the village of Bolgheri.

Why it's a classic The estates behind the wines collectors queue for.

⏱️ Full day
🍷 Three estates of your choice
🌲 Viale dei Cipressi
💶 €600 / person

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A truffle dog and its hunter unearthing a white truffle in the woods of San Miniato

06 · San Miniato · about 45 min from Florence

Truffle hunting in Tuscany: a real hunt with working dogs, then sparkling wine

In the woods above San Miniato, a family that has trained truffle dogs for three generations takes you hunting.

Follow the hunter and her dog through the woods, sit down to a lunch built around what you find, then end the day at a cellar devoted to sparkling wine.

Why it's a classic A real hunt, not a show: what you eat depends on the dog.

⏱️ 8 hours
🐕 Hunter & her dog
🥂 Truffle lunch & bubbles
💶 From €280 / person, group of 8 · €400 for 2

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At a glance

Tuscan Classics compared

Day trip	From Florence	Duration	Best for	Best season	From*
Chianti Hidden Gems	about 40 min	4–8 h	First-time visitors, wine lovers	All year	€220
San Gimignano & Siena	about 1 h	9 h	Art, history, first trips	All year	€220
Montalcino	about 1h45	8 h	Serious red wine lovers	All year	€250
Nobile di Montepulciano	about 1h30	8 h	Wine, views, photography	All year	€230
Bolgheri	about 1h45	Full day	Collectors, Bordeaux-blend fans	All year	€600
Truffle Hunting & Bubbles	about 45 min	8 h	Food lovers, families	All year (white Oct–Dec)	€280

*Per person for a private group of eight. Each tour page shows the price for two and lets you check the exact price for your group.

Questions

Tuscan Classics: frequently asked questions

What are the Tuscan Classics?

Our private day trips from Florence to Tuscany's most famous wine areas and towns: Chianti Classico, San Gimignano and Siena, Montalcino, Montepulciano, Bolgheri and the truffle woods of San Miniato. The places are famous; the way we visit them is not, with family estates, quiet hours and long lunches.

Are these tours private?

Yes. Every tour is private, just for your group, with door-to-door transport from your hotel or apartment in Florence and an English-speaking guide.

Which classic is best for a first trip to Tuscany?

Chianti Hidden Gems is the easiest introduction to Tuscan wine, and San Gimignano & Siena is the best day for art and history. For great red wine, choose Montalcino or Montepulciano.

How do prices work?

Prices are per person and drop as the group grows. The 'from' price is for a group of eight; each tour page shows the price for two and lets you check the exact price for your group.

Can we combine two classics?

Yes. Many guests book two days, for example Chianti and Montalcino. Tell us your dates and we suggest the best order.

Not sure which classic to choose?

Tell us what you love and how many you are: we will suggest the right day and reply personally, usually within 24 hours.

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