Florence: Chianti Wine Tasting Day Trip｜Italy

Escape the crowds of Florence and explore medieval Siena and San Gimignano before an authentic lunch and fine wine tasting at a historic Tuscan winery for an unforgettable experience.

Siena: Echoes of the Middle Ages Our first destination is Siena, a city that feels like a living museum. We’ll guide you into the heart of the UNESCO-listed center to stand in the shell-shaped Piazza del Campo. As you walk the brick-paved square, you’ll feel the lingering energy of the Palio, the legendary medieval horse race that defines the city's soul.

Siena is a feast for the senses. Before we leave, we’ll take a moment for a true Italian ritual: a perfect espresso paired with the city's artisanal treasures. Taste the spice-rich Panforte, the honeyed Panpepato, and the melt-in-your-mouth Ricciarelli almond cookies—recipes that have remained unchanged for centuries.

The Manhattan of the Middle Ages Next, the skyline of San Gimignano appears on the horizon like a stone crown. Known as the "City of the Hundred Towers," this hilltop fortress is a labyrinth of medieval streets and timeless charm. While the world knows Chianti, San Gimignano holds a secret: Vernaccia, Italy’s first DOCG white wine, grown in these very soils since the 1200s. You’ll have time to explore the hidden courtyards and artisan boutiques that make this village a sanctuary of Tuscan culture.

The Feast: A Storied Winery Experience The highlight of the afternoon is an exclusive visit to a family-run estate. This isn't just a quick tasting; it’s an immersion. We’ll go behind the scenes into the cool, oak-scented cellars to see where the grape’s journey from vine to bottle begins.

Gather around a farmhouse table for a long, traditional Tuscan lunch. You will be guided through a professional tasting of 10 different labels, including robust Chianti Classicos and elegant whites. Each glass is paired with local delicacies—extra virgin olive oil, aged cheeses, and cured meats—allowing you to taste the terroir of the land you’ve spent the day exploring.

Return to Florence As the golden hour light hits the vineyards, we’ll begin our smooth journey back to Florence, leaving you with the lingering taste of Tuscany and the memories of a day spent like a local, not a tourist.