Florence Cathedral at sunset

Tuscany

Chianti Wine Tours and Multi-Day Wine Journeys in Tuscany

Multi-day wine journeys through Chianti, Montepulciano and the Val d'Orcia, not a day trip out of Florence.

About chianti wine tours in Tuscany

Most Chianti wine tours sold online are half-day excursions from Florence: a coach, two estates and back in the city by six. Ours are different. We build multi-day journeys where the wine roads are the itinerary, with nights in the hill towns, tastings booked directly with the producers and a driver who knows which cellars are worth the detour.

The heart of the route is the Chianti Classico area between Florence and Siena, the strip of vineyards and olive groves around Greve, Panzano, Radda and Castellina. This is where the black rooster seal comes from, and where estates are small enough that the person pouring the wine is often the person who made it.

South of Siena the journey continues into the Val d'Orcia, with Montalcino and its Brunello, Montepulciano and its Vino Nobile, and Pienza for pecorino cheese. Distances between the three towns are short, so a single base is usually enough for two or three days of tastings, cellar visits and long lunches.

A tasting with us is a guided visit, not a counter service: a walk through the vineyard and the cellar, an explanation of the denomination and the ageing rules, then four to six wines poured with local cheese, salumi and bread. Where the estate has a kitchen we add a full lunch, and where it has rooms we can stay the night.

Wine journeys work all year, but September and October bring the harvest and the warmest colours, while April to June gives green hills and quieter cellars. Groups are kept small, transfers are private, and the whole itinerary can be combined with Florence, Siena or a few days on the coast.

Country road between Tuscan vineyards

The Chianti wine roads

The Chiantigiana road runs from Florence to Siena through the heart of the Classico area, past Greve, Panzano, Radda and Castellina. The estates here are mostly family owned, with cellars cut into the hillside and tasting rooms that hold a dozen people at most. We plan two visits a day, morning and late afternoon, with lunch in a village in between.

Cypress-lined road in the Val d'Orcia at sunrise

Montepulciano and the Val d'Orcia

Further south the hills open out and the wines change: Brunello di Montalcino, aged five years before release, and Vino Nobile di Montepulciano, whose cellars run under the streets of the old town. Pienza, ten minutes away, supplies the pecorino that goes with both, and the clay hills of the Val d'Orcia make the drive between them part of the visit.

Chianti wine tours in Tuscany: our tours

Florence Cathedral at sunset
Price on request

Toscana

Cycling and tastings between Florence, Siena and the Chianti hills.

12 days / 11 nights · Florence, Siena, Chianti

Chianti Wine Tours and Multi-Day Wine Journeys in Tuscany: frequently asked questions

Is this a day trip from Florence?
No. These are multi-day journeys with nights in the wine country, usually three to seven days between Chianti, Montalcino and Montepulciano, with Florence or Siena at either end if you want them.
What does a tasting include?
A guided walk through the vineyard and cellar, an explanation of the denomination and ageing rules, then four to six wines with local cheese, salumi and bread. A full lunch is added where the estate has a kitchen.
What is the difference between Chianti Classico, Brunello and Vino Nobile?
Chianti Classico comes from the hills between Florence and Siena, Brunello from Montalcino and Vino Nobile from Montepulciano. All three are Sangiovese based, but the ageing rules and the character of the wine differ.
When is the best time for a wine tour in Tuscany?
September and October for the harvest and the colours, April to June for green hills and quieter cellars. Most estates are open all year except during August holidays.
Is transport included?
Yes. Private transfers and a driver are part of the programme, so nobody in the group has to skip the tastings.

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