Information about the Tuscan Trip

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.

This Tuscan Experience for 4 Includes:

• 5-night stay in a 2-bedroom apartment in Cortona, Italy
  • Cortona is approximately a 1.5-hour drive from Florence and a 2.5-hour drive from Rome. 
  • Nearby cities: Perugia 45 km; Siena 70 km; Florence 100 km; Rome 205 km; Pisa 200 km
• This package is available from November – March.
• Two curated seasonal signature experiences (based on month of travel)
• Booking & concierge service

Additional Information

• Reservations are subject to availability, blackout dates, and major holidays. 
• Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
• Ground transportation is the responsibility of the winner unless otherwise stated.

Blackout Dates

The week of major holidays and major local events. Additional dates may apply. Travel is available from November – March.