Our driver will pick you up and guide you along the Via Chiantigiana, a picturesque route through the Tuscan countryside starting from the Arezzo area. This scenic road winds past rolling vineyards, olive groves, and iconic cypress trees, showcasing the timeless beauty of Chianti. Along the way, you’ll pass charming medieval villages, rustic stone farmhouses, and historic wineries, surrounded by landscapes that feel like living paintings. The Via Chiantigiana offers a perfect introduction to Tuscany’s rich wine culture and peaceful rural charm.

After about an hour, you’ll arrive in Castellina in Chianti, a charming town steeped in medieval history. Stroll through its historic center, where artisan shops and traditional wine and cheese boutiques line the streets. Once a strategic site in the battles between Florence and Siena, Castellina is rich in history, with underground vaulted passageways and a medieval fortress that now houses a fascinating museum. As you explore, enjoy breathtaking panoramic views along the scenic country roads. The surrounding landscape is a feast for the senses, with rolling wheat fields, lush vineyards, and cypress-lined curves filling the air with the unmistakable aromas of the Tuscan countryside.

For lunch, we will visit a family-run Tuscan farm, where you’ll experience the true warmth of rural Italy, surrounded by vineyards and rolling hills. Meet the local winemaking family and discover the secrets of traditional Tuscan wine-making. • Enjoy a genuine homemade 3-course meal made with fresh, local ingredients: • Bruschettas, artisanal cold cuts (salami, prosciutto), and pecorino cheeses • Homemade pasta with traditional Tuscan sauces • Paired with a guided tasting of 6 exceptional wines, from crisp whites to Chianti DOCG, Chianti Riserva, and bold Super Tuscans Finish with extra virgin olive oil tastings, savoring the authentic flavors of Tuscany, crafted with care by a family who has nurtured their land and traditions for generations.

The final stop will be at a second family-run Chianti winery, a charming estate in the heart of Chianti. Here, wine has been crafted for generations using traditional methods, guided by expert winemakers, resulting in limited but exceptional bottles with a unique character. Enjoy a special guided wine tasting, savoring the rich aromas and flavors of their carefully produced Chianti reds as well as prestigious white wines, each reflecting the expertise and passion of the family. After this delightful stop, we’ll return you to your location—whether it’s your hotel, private flat, or B&B—concluding a perfect day exploring the flavors and beauty of Tuscany.