Private Chianti Wine Tasting Tour from Florence: Greve & Castellina
Rolling hills, ancient villages, and the legendary wines of the Chianti Classico heartland
This private Chianti wine tasting tour from Florence takes you deep into the Tuscan countryside, where terraced vineyards, silvery olive groves, and hilltop medieval settlements define one of Italy's most celebrated wine regions. It is an unhurried, fully private experience designed for couples, families, and small groups who want substance over spectacle.
The route follows the historic Wine Route through the Sienese hills, passing castles, cypress-lined roads, and organic estates before arriving at a carefully selected winery near Castellina in Chianti. There you meet Silvano, the resident winemaker, who leads a private tasting of seven organic wines alongside extra-virgin olive oil and balsamic vinegar, accompanied by a generous spread of local charcuterie, cheeses, bruschetta, a pasta or ribollita course, and the classic pairing of Vin Santo with cantucci biscuits.
The afternoon divides between two distinctive Chianti towns. Castellina in Chianti rewards exploration with its Etruscan roots, Bronze Age heritage, and stone-paved lanes that have changed little over centuries. Greve in Chianti, long regarded as the gateway to the region, centers on a porticoed piazza anchored by a monument to explorer Giovanni da Verrazzano, surrounded by artisan butchers, specialty food shops, and the living commercial tradition that has defined the town since the fourteenth century.
Tour Highlights
Private tasting of seven organic wines including Chianti Classico DOCG, Chianti Classico Riserva, and a premium estate selection led by winemaker Silvano.
A full sit-down tasting table with local cold cuts, cheeses, bruschetta, a pasta or ribollita course, and the traditional Vin Santo with cantucci dessert.
Guided walk through Castellina in Chianti, an Etruscan city with Bronze Age origins, stone streets, and a compact historic center rich in archaeological heritage.
Exploration of Greve in Chianti, the traditional gateway town of the Chianti region, with its distinctive porticoed square and the Falorni butcher shop.
Door-to-door private transport from your Florence accommodation with an English-speaking driver, including scenic stops along the Wine Route for photographs.
Tasting of extra-virgin olive oil and balsamic vinegar directly at the organic estate, with explanation of production methods from source to table.
Optional detour to the medieval village of Montefioralle, birthplace of Amerigo Vespucci, if time permits on the return journey to Florence.
Itinerary
Your private driver collects you directly from your Florence accommodation and heads south through the rolling Sienese hills. The route follows the historic Wine Route, winding past vineyards, cypress trees, olive groves, and stone farms as the Chianti countryside unfolds around you.
Arrive at a select organic farm near Castellina in Chianti for an exclusive private session with winemaker Silvano. He presents seven organic wines, including Chianti Classico DOCG and Chianti Classico Riserva, alongside balsamic vinegar and extra-virgin olive oil, explaining each wine's origin, character, and production method.
Following the wine presentation, enjoy a generous spread of local specialties: cold cuts, hams, cheeses, bruschetta, and specialty olives, followed by a pasta or ribollita course prepared by the estate chef. The meal concludes with Vin Santo and cantucci, the classic Tuscan digestif pairing.
Explore the ancient streets of Castellina in Chianti, a settlement with roots stretching to the Bronze Age and a well-preserved Etruscan heritage. The compact historic center features stone lanes, medieval architecture, and local shops offering wine and olive oil from surrounding estates.
Visit Greve in Chianti, whose porticoed central piazza has served as the commercial heart of the Chianti trade since the fourteenth century. The square is anchored by a statue of Giovanni da Verrazzano, the Florentine navigator who explored the North American coast; surrounding it are specialty food shops including the renowned Falorni butcher.
Your driver returns you to your Florence accommodation, with a possible stop at the medieval village of Montefioralle — birthplace of Amerigo Vespucci — if the schedule allows. The return journey retraces the scenic Wine Route through the Chianti hills.
What Is Included
Included
- Private round-trip transport from your Florence accommodation
- English-speaking private driver throughout the day
- Private guided wine tasting with winemaker Silvano (7 organic wines)
- Tasting of extra-virgin olive oil and balsamic vinegar
- Tasting lunch with charcuterie, cheeses, bruschetta, pasta or ribollita, and Vin Santo with cantucci
- Guided visit to Castellina in Chianti
- Free time in Greve in Chianti with orientation
- Scenic stops along the Wine Route for photography
Not Included
- Personal purchases at shops and markets
- Gratuities for driver and winemaker (discretionary)
- Additional food or beverages beyond the included tasting lunch
- Travel insurance
Important Information
Reserve Your Private Chianti Experience
Secure your spot on this private full-day journey through the vineyards and hilltop villages of the Chianti Classico zone, departing directly from your Florence hotel.
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