Visit Chianti: 3 Cellars, Tuscan Lunch & Private Wine Tour
A full-day private journey through three Chianti wineries, a family farm lunch, and the rolling Tuscan countryside.
This private Chianti wine tour takes you beyond the usual tasting room and into working cellars, organic vineyards, and a family-run farmhouse, giving you a grounded understanding of why Tuscany is one of the world's most respected wine regions. Built on twenty years of curated relationships with local producers, the itinerary balances education, gastronomy, and scenery across six hours. Hotel pickup and drop-off in Florence are included, so the day begins the moment you step outside your door.
The route follows the Via Chiantigiana (SS222), the scenic road that winds through cypress-lined hills connecting Florence to Siena. Along the way, your driver stops at viewpoints that frame the vineyard landscape in a way few visitors experience outside of a car window. The pace is unhurried, and time is given to understand what you see rather than simply passing through it.
Each of the three wineries on this itinerary represents a distinct philosophy: one focused on heritage and tradition, one committed to organic and natural farming, and one oriented toward comparing how terroir shapes the same grape differently. By the end of the day, you will have tasted wines ranging from Chianti Classico and Chianti Colli Senesi to Super Tuscan blends, 100% Sangiovese, and Vernaccia di San Gimignano, alongside a full Tuscan lunch with homemade pasta, bruschetta, pecorino, and five types of local extra virgin olive oil.
Tour Highlights
Private hotel pickup and drop-off in Florence, with a scenic drive along the Via Chiantigiana through the Chianti countryside.
Visits to three distinct family-run wineries, each representing a different approach to Tuscan viticulture and cellar management.
Guided tastings of DOCG and IGT wines including Chianti Classico Black Rooster, Chianti Riserva, Super Tuscan, and Vernaccia di San Gimignano.
A traditional Tuscan farm lunch with homemade pasta, cold cuts, bruschetta, five olive oils, and three balsamic vinegars.
In-depth explanations of DOCG certification rules and the production differences between red, white, and natural wines.
A final comparative tasting designed to illustrate how soil type, altitude, and sun exposure influence flavor in the same grape variety.
Photo stops at panoramic viewpoints across the Chianti hills, including cypress roads and vineyard vistas typical of the Tuscan landscape.
How the Day Unfolds
Your guide picks you up at your Florence accommodation and heads south along the SS222, stopping at scenic overlooks for photos of vineyards and cypress-lined roads. This introduction to the landscape sets the context for everything you will taste during the day.
The first stop is a family winery with roots going back to 1926, producing Chianti Classico across several style levels. After a tour of the cellar, a guided tasting covers Chianti Classico, Riserva, Super Tuscan, and 100% Sangiovese, with the guide explaining how each wine reflects its classification and aging process.
A second family-run organic winery provides the setting for a full sit-down Tuscan meal: homemade pasta, bruschetta, pecorino cheese, cold cuts, and a selection of five extra virgin olive oils and three balsamic vinegars. The meal is paired with Chianti Colli Senesi, Tuscan reds, and a rosé, and the host walks through the pairing logic.
The afternoon stop focuses on comparison: a cellar tour followed by a tasting of approximately five wines, typically including Vernaccia di San Gimignano, a white Tuscan, and a Super Tuscan, alongside a Chianti Classico Black Rooster. The guide explains how the same Sangiovese grape can produce very different results depending on location and winemaker choices.
Your driver returns you to your Florence accommodation by the end of the afternoon. By this point you will have visited three producing estates, tasted more than twelve wines, and eaten a full traditional Tuscan lunch in the countryside.
What Is Included
Included
- Private hotel pickup and drop-off in Florence
- Transportation throughout the day in a private vehicle
- Guided visits to three wineries and their cellars
- Wine tastings at all three estates (12+ wines total)
- Traditional Tuscan farm lunch with food pairings
- Tasting of five extra virgin olive oils and three balsamic vinegars
- English-speaking guide with twenty years of regional expertise
- Photo stops along the Via Chiantigiana
Not Included
- Gratuities (at your discretion)
- Additional beverages beyond the guided tasting selections
- Wine purchases at wineries (available at your own cost)
- Travel insurance
Important Information
Reserve Your Private Chianti Wine Tour
Spaces on this private tour are limited by design. Confirm your date to secure hotel pickup, three winery visits, and a full Tuscan farm lunch across six hours in the Chianti hills.
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