HIDDEN TUSCANY: ALL-INCLUSIVE VACATION

Unwinding in the Val d’Orcia Landscape

Private transfer with chauffeur from the airport to your beautifully restored historical estate in the heart of the Val d’Orcia (UNESCO). Check-in, settle into your room, and unpack. In the afternoon, meet your Italy Heritage Trails coordinator for a welcome briefing over an artisanal cocktail. Enjoy a candlelit welcome dinner featuring zero-kilometer Tuscan ingredients and organic extra virgin olive oil. Overnight in Val d’Orcia.

Pecorino Cheese Tastings and Ideal Architectural Design

Breakfast at the estate. Begin your journey in Pienza, the "ideal city" of the Renaissance commissioned by Pope Pius II. Enjoy a guided walking tour along the romantic lanes (Via dell'Amore, Via dell'Bacio) overlooking the clay hills, followed by an exclusive tasting of artisanally aged Pecorino di Pienza cheese. In the afternoon, move to the fortified village of San Quirico d’Orcia to stroll through the geometric perfection of the 16th-century Leonini Gardens. Dinner at a traditional trattoria. Overnight.

Gregorian Chants, Ancient Abbeys, and Red Wine Heritage

Breakfast. Drive through panoramic cypress paths to the solitary Abbey of Sant’Antimo, a Romanesque masterpiece hidden in a valley, where you can listen to the echoing tradition of Gregorian chants. Continue to the hilltop fortress of Montalcino. After a guided walk of its medieval defense walls, visit a historic, family-run winery for a private cellar tour and an experiential lunch paired with world-renowned Brunello di Montalcino DOCG. Free afternoon for independent exploration. Dinner at leisure. Overnight.

Dramatic Volcanic Cliffs and the Secret Roads of an Ancient Civilization

Breakfast. Today, journey south to the dramatic Maremma region to discover the "Tufa Towns." Arrive in Pitigliano, a breathtaking village carved directly into a sheer volcanic tuff cliff, seemingly suspended in mid-air. Explore its ancient Jewish Ghetto, known as "Little Jerusalem." Continue to the silent, fairy-tale hamlet of Sovana to walk through the Vie Cave—mysterious, deep pathways hand-carved into the rock by the ancient Etruscans over 2,500 years ago. Return to the estate for dinner and overnight.

Healing Volcanic Springs and the Footsteps of Medieval Pilgrims

Breakfast. Visit Bagno Vignoni, a unique village built around a massive, steaming Renaissance thermal pool instead of a main square. Learn about the Roman emperors and saints who bathed here along the ancient Via Francigena pilgrimage route. In the afternoon, ascend to the rugged fortress town of Radicofani, dominated by its imposing tower that once guarded the border of the Grand Duchy of Tuscany. Enjoy panoramic views stretching out to Mount Amiata. Dinner and overnight.

Stepping Inside a Medieval Fortress and Settling into Wine Country

Breakfast and check-out from Val d’Orcia. Travel north toward the rolling hills of Chianti. En route, stop at Monteriggioni, an iconic, perfectly circular walled castle that Dante Alighieri famously compared to giants in his Divine Comedy. Walk the intact parapet walls for sweeping views over the countryside. Continue to your new boutique accommodation—a historic Chianti wine estate. Welcome dinner featuring the authentic Bistecca alla Fiorentina paired with Chianti Classico Gran Selezione. Overnight in Chianti.

The Medieval Skyline and the Red-Brick Home of Boccaccio

Breakfast. Spend the morning in San Gimignano (UNESCO), the "Manhattan of the Middle Ages," famous for its 14 surviving medieval towers. Your heritage guide will unveil the ancient rivalries between the Guelph and Ghibelline families. Taste award-winning saffron-infused gelato in Piazza della Cisterna. In the afternoon, ride a funicular railway up to Certaldo Alto, a stunning red-brick hilltop hamlet untouched by time, where the famous medieval author Giovanni Boccaccio lived and wrote. Return to the estate for dinner and overnight.

Etruscan Tombs, Underground Tunnels, and the Black Rooster Legend

Breakfast. Dedicate the day to the historic capitals of the Chianti League. Start in Castellina in Chianti to walk through the Via delle Volte, a mysterious underground vaulted street used for military defense, and explore its massive Etruscan burial mounds. Continue through the winding vineyard roads to Radda in Chianti and Gaiole in Chianti, learning about the ancient legend of the Black Rooster. Stop at an artisanal terracotta workshop to see how traditional Tuscan amphorae are made. Dinner at leisure. Overnight.

Winding Alleyways, Ancient Amphitheaters, and a Panoramic Tuscan Apericena

Breakfast. Free morning to relax by the estate's panoramic pool. In the afternoon, drive to Volterra, a wind-swept hilltop stronghold boasting 3,000 years of history. Tour a traditional workshop to watch local master artisans hand-carve translucent alabaster stone, a craft passed down since Etruscan times. Visit the Roman Amphitheater before heading to a historic vineyard on the ridges of the hills. Conclude your extraordinary journey with a farewell apericena celebration, tasting artisanal cold cuts, pappa al pomodoro, and a selection of local wines as the sun sets over the Tuscan hills. Return to the estate. Overnight.

Breakfast at the estate. Check-out and private transfer with chauffeur back to Florence or Pisa Airport for your departure flight, carrying home the timeless stories and authentic heritage of Tuscany’s most beautiful trails.