Italy's Best Kept Secret

5 Nights | 4 Guests | Tuscany (Cortona), Italy

A Taste of Tuscany in Its Most Authentic Season for 4

Airfare not included. Two years to travel.

Experience for 4 Includes:

• 5-night stay in a 2-bedroom apartment in Cortona, Italy
• Two curated seasonal signature experiences (based on month of travel)
• Winspire booking & concierge service
  

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.

Luxury Apartment Stay

Your home in Cortona is a charming private apartment, blending classic Tuscan character with modern comforts. From its central location, you'll be just steps away from Cortona's shops, trattorias, and piazzas. Toast your arrival with a chilled bottle of Champagne and let Tuscany's rhythm welcome you into its timeless embrace.

Additional Information: Climbing a staircase is required to access apartment. The building does not have an elevator.

Please note:

• This package is available from November - March.
• Christmas Markets traditionally operate Thursday through Sunday. Exact opening dates and hours may vary slightly each year and will be confirmed closer to your travel dates.
• In-residence dining menus are seasonal and chef curated. Menus are not customizable or pre-selected in advance, ensuring the authenticity, integrity, and freshness of each culinary experience.
• While we aim to provide flexibility whenever possible, certain seasonal experiences are tied to specific agricultural or cultural windows and cannot be shifted outside their designated timeframe.
  

Package Redemption: Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date. 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.

Auction Fulfillment Contact Info: If you have questions, please contact the foundation's Auction Fulfillment Coordinator at [email protected] or (859) 488-1740.

No Refunds: All sales are FINAL. Experiences may be subject to change based on vendor regulations, availability, and/or tariffs. In the rare event an experience becomes unavailable, the vendor/Foundation team will make every reasonable effort to fulfill the experience with an equally comparable package.