The grandness of Italy is not nestled tidily in the past or in its idyllic clime or some genetic inheritance but in the way thousands of years of history and tradition find creative voice and resonance in our modern world, in this spectacular place. The Olive Road will take you there. To a luxurious 11th century castle perched on a hillside in Tuscany for a week living la dolce vita, basking in the wonders and traditions of the region that gave birth to Dante Alighieri and Chianti. In the very castle where Dante himself stayed and was inspired to write The Divine Comedy.

Highlights & Details

Slow Travel for Deeper Connection: With a slower-paced itinerary, this trip emphasizes meaningful interactions with our Tuscan friends, allowing you to truly feel the rhythm of Tuscan life.
Step back in time as we inhabit our very own 11th century castle in Tuscany’s mountains, the very same castle which inspired Dante himself.
Shop at local markets with our resident chef and help create al fresco feasts
Farm-to-Table Culinary Experiences: Savor authentic Tuscan cuisine through hands-on cooking classes and farm visits, where you’ll learn to make fresh pasta, cheese, and olive oil from local artisans.
Traditional Medieval meal in our very own medieval castle.
Cultural Workshops: Participate in private workshops with Tuscan artisans, learning centuries-old crafts like Tuscan linens and luxury wool production.
Endless optional enrichment, including: Fly Fishing in the Arno river, horseback riding in the Casentino forest, guided hikes, and massages in the castle
Sunset Apricena atop our castle: Enjoy an unforgettable dinner on the roof of our own 11th century castle, marveling at the backdrop of Tuscany’s mountains.