Private Chianti Wine Tour with Castellina Visit from Rome
A full-day journey through Tuscan vineyards, historic hilltop villages, and award-winning cellars
This private Chianti wine tour from Rome takes you deep into the rolling hills of Tuscany for an immersive day of wine tasting, cultural discovery, and scenic countryside roads lined with olive groves and cypress trees.
Departing in a luxury vehicle with a professional English-speaking driver, you will travel through one of Italy's most celebrated wine-producing landscapes, where every bend in the road reveals a new postcard-worthy view. The journey is designed for couples, families, and wine enthusiasts who want a relaxed yet enriching experience without the constraints of a group tour.
At a carefully selected local winery, an expert guide walks you through a tasting of up to seven organic wines, including Chianti Classico DOCG and Chianti Riserva, paired with regional specialties such as cured meats, aged cheeses, bruschetta, handmade pasta, and the traditional sweet wine Vin Santo served with cantucci biscuits.
The day also includes a walking visit to Castellina in Chianti, a well-preserved hilltop town whose roots stretch back to the Bronze Age and whose Etruscan heritage is still visible in a remarkable tomb dating to the seventh and sixth centuries BC. Stone streets, artisan wine shops, and a quiet historic center make this stop one of the highlights of the entire day.
Tour Highlights
Taste up to seven organic wines, including Chianti Classico DOCG and Chianti Riserva, guided by winemaker Silvano at a family estate.
Walk the stone streets of Castellina in Chianti and explore a hilltop town with roots tracing back to the Bronze Age.
Travel scenic hill roads through cypress-lined landscapes, vineyards, and olive groves that change color with every season.
Discover an ancient Etruscan tomb dating to the seventh and sixth centuries BC, a rare archaeological highlight within the town.
Enjoy a generous tasting table featuring local cold cuts, hams, cheeses, olive oil, balsamic vinegar, pasta, and Vin Santo with cantucci.
Travel in comfort aboard a private luxury vehicle with a professional driver, with no shared itinerary or fixed group stops.
Stop at any point along the wine road for photographs whenever a landscape or view catches your eye.
Itinerary
Your driver collects you directly from your accommodation in Rome in a luxury private vehicle. The journey heads north into Tuscany, following scenic hill roads through the Chianti wine country, passing farms, medieval castles, cypress avenues, and vineyard-covered slopes.
As you travel deeper into the Chianti production zone, the driver narrates the landscape and its significance to Italian wine culture. Photo stops are available at any point along the route whenever a view or detail warrants a pause.
The first stop is the hilltop town of Castellina in Chianti, where you explore the stone-paved historic center, browse artisan wine and oil shops, and visit the ancient Etruscan tomb on the outskirts of town. This settlement has been continuously inhabited since the Bronze Age and retains a distinctly authentic character.
At a selected family estate, winemaker Silvano hosts a guided tasting of up to seven organic wines, explaining the history of each label, the production methods, and how to read the characteristics of Chianti Classico and Riserva. Balsamic vinegar and extra virgin olive oil are also presented at the table.
The tasting is accompanied by a spread of local specialties including cured meats, hams, aged cheeses, olives, bruschetta, and a choice of handmade pasta or the traditional Tuscan soup Ribollita. The session concludes with Vin Santo and cantucci biscuits.
After the winery visit, your driver returns you directly to your accommodation in Rome. The return route follows the same scenic countryside, allowing for a relaxed end to the day.
What Is Included
Included
- Private luxury vehicle with professional driver
- English-speaking guide and driver throughout
- Guided tasting of up to 7 organic wines including Chianti Classico DOCG and Riserva
- Tasting of extra virgin olive oil and balsamic vinegar
- Regional food pairing with cold cuts, cheeses, bruschetta, pasta or Ribollita, and Vin Santo with cantucci
- Visit to Castellina in Chianti historic center
- Hotel pickup and drop-off in Rome
- All transportation during the tour
Not Included
- Personal expenses and souvenirs
- Additional wine purchases at the winery
- Travel insurance
- Gratuities for driver and guide
Important Information
Reserve Your Private Chianti Wine Tour
Secure your place on this exclusive full-day tour from Rome and discover the wines, landscapes, and history of the Chianti Classico region at your own pace.
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