Full Day PRIVATE Guided Tour in Val D'Orcia Region

Brunello Wine Tasting. After being picked up from your hotel, we will head south, passing through Siena, and enter the heart of the Val d’Orcia. We will reach the foothills of Montalcino, where our winemaker will be waiting for us.This is a very small, family-run boutique organic winery that continues to impress anyone approaching the famous Brunello wines, even for the first time. Here, we will enjoy our first tasting, guided by the staff or directly by our artisan, who is also the owner of the winery.For those who prefer not to join the tasting, you can wander through the picturesque streets of Montalcino, discovering its charming squares, historic buildings, and timeless Tuscan atmosphere.

Monticchiello: A Medieval Gem Off the Beaten Path. Discover Monticchiello 🏰, a medieval village frozen in time, just 15 minutes from Pienza. Every stone tells stories of courage and loyalty to Siena, a place that held out until the very end against the Florentines in 1559.For over five centuries, the families of the village actively participated in the life of the municipality, giving each a voice in the heart of the community.As we wander through charming streets, we’ll experience the true Tuscan atmosphere: few tourists, pure authenticity, postcard-perfect views, and timeless corners.To finish, a meal at one of the local restaurants 🍝🌄, paired with local wine 🍷, for a taste of history, tradition, and genuine flavors.

Pienza. For those looking for a more classic tourist experience, Pienza is the perfect stop—while Monticchiello remains an option, the choice is yours! The remarkable history of Pienza is concentrated in just six years (1458–1464) during the pontificate of Silvio Piccolomini, its most illustrious citizen. Elected Pope, Pius II commissioned the Florentine architect Bernardo Rossellino to transform his native village, then called Corsignano, into a new city. Together they built the Cathedral, Palazzo Piccolomini, and other significant buildings, including palaces for visiting cardinals. Corsignano was renamed Pienza, in honor of the Pope.After the death of Pius II, construction slowed, and the city returned to its peaceful rural life—but the masterpieces of its brief golden age remained. Their historical and artistic significance led UNESCO to declare Pienza a World Heritage Site in 1996. In 2004, the Val d’Orcia received the same recognition, protecting a historic landscape shaped by human hands in perfect harmony with nature’s beauty.Here, you can stroll through charming streets, admire Renaissance architecture, and soak in views that have inspired generations—a magical pause in the heart of Tuscany.

Church of Vitaleta.. La Cappella della Madonna di Vitaleta, nascosta tra le dolci colline della Val d’Orcia vicino a San Quirico d’Orcia, sembra piccola e discreta, ma possiede un fascino straordinario. Incorniciata dai cipressi che si stagliano verso il cielo, è diventata protagonista di alcuni dei paesaggi più celebri e fotografati al mondo.Per secoli è stata un luogo di profonda devozione, dedicato alla Madonna della Consolazione, e nel 1553 vi fu collocata una statua della Vergine attribuita ad Andrea della Robbia. La leggenda narra che fu la Madonna stessa, apparendo a una pastorella, a indicare ai fedeli dove trovare la statua a Firenze, destinata a illuminare la piccola cappella.Oggi la statua originale è custodita a San Quirico d’Orcia, ma la cappella continua a incantare chi la osserva, sospesa tra arte, storia e la magia dei paesaggi toscani. Guardarla è come immergersi in un dipinto vivo, dove la luce e la natura raccontano storie antiche.

Wine tasting and visit to the historic cellars in Montepulciano. Said to be one of the most beautiful wineries in the world 🍇… and I can truly say, it lives up to its reputation! Visiting this winery is like taking a journey through time and history, right into the heart of Tuscany. Here lies the very essence of this sweet land: wine, crafted centuries ago by our distant ancestors, the Etruscans, long before the Christian era 🏺.Our visit is in Montepulciano, an effervescent town full of charm, with bustling streets, quaint wine shops, and delicious local cuisine 🍷🍝. Strolling through its alleys is an experience in itself, where history and modern life blend perfectly.This will be our last stop, but certainly not the last in terms of beauty ✨. After the guided tour, we’ll taste the famous Nobile di Montepulciano wine of the historic De’ Ricci family, a true treasure of the region. Then, we’ll return to Florence in just 90 minutes, enjoying a comfortable ride back.