There is a side of Tuscany few travelers ever see — a quieter, more intimate season when traditions unfold naturally and the rhythm of life slows to something deeply authentic. Italy’s Best-Kept Secret invites you to experience Tuscany as locals do, beyond the crowds and beneath softer skies, where every moment feels personal and unhurried.
From autumn harvest rituals to candlelit winter dinners, from private family tables to the first stirrings of spring in the vineyards, this curated off-season journey reveals a Tuscany that is lived rather than observed. Based in the timeless hill town of Cortona, your five-night stay becomes the setting for a signature seasonal experience tied to the month of travel — each thoughtfully designed to immerse you in the region’s culture, cuisine, and enduring traditions.
This is not peak-season Italy. This is Tuscany at its most soulful.
Experience for 4 Includes:
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- 5-night stay in a 2-bedroom apartment in Cortona, Italy
- Two curated seasonal signature experiences (based on month of travel)
- Booking & concierge service
Restrictions: Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Airfare and ground transportation are not included.
Donated By: Friends of St. Jude Children's Research Hospital