The adventure begins in the medieval village of Monteriggioni, where you join your group and set off to explore the rolling hills of Chianti. Immerse yourself in Tuscany's winemaking heritage with a visit to a family-run winery. There you will taste three distinct wines at the first cellar and learn about local production methods while sampling extra virgin olive oil and rustic Tuscan bread. Knowledgeable guides enrich the experience with stories about the region's history, art and rural culture.
From Chianti you continue into the scenic Val d'Orcia, arriving in Pienza — a compact town famed for its harmonious Renaissance architecture and panoramic views. Enjoy free time to wander historic lanes, visit artisan shops or relax over a leisurely lunch at your own pace.
The tour proceeds to Montepulciano, a hilltop town known for its elegant churches and Renaissance palazzi. Here you can savour traditional Nobile di Montepulciano wine and take in spectacular vistas of rolling vineyards and cypress-lined roads. A second winery stop offers further tastings paired with local snacks, deepening your appreciation of Tuscan flavours and winemaking traditions.
The day concludes with a comfortable drive back to Siena, allowing time to reflect on a full day of culture, food and outstanding countryside scenery.
Read moreMinimum legal drinking age applies
Notify operator of dietary requirements in advance
Sun protection and a camera recommended
Comfortable walking shoes and weather-appropriate clothing
Valid photo ID required for alcohol tastings
Highlights of the tour
This carefully curated day trip blends culture, gastronomy and scenic drives to deliver an authentic Tuscan experience.