Under the Tuscan Sun: Wine, Cuisine & Charm in Cortona

3 or 4 Nights | 4 Guests | Tuscany (Cortona), Italy

Italy Escape for 4 with Wine Tasting & Private Chef Dinner

Airfare not included. Two years to travel.

This Experience for 4 Includes:

• Your choice of a 3-night weekend (Fri-Sun) or 4-night weekday (Mon-Thu) stay in Tuscany for 4 guests
• Wine tasting in Cortona featuring 4 local wines from one of the world's most celebrated regions
• Private chef-prepared 3-course dinner served in your apartment
• Winspire booking & concierge service - seamless support from planning to departure

Stay in the Heart of Cortona

Your private apartment is nestled within Cortona's medieval walls, offering both modern comfort and old-world charm. Wake up to sunlight spilling across terracotta rooftops, then step outside to discover markets filled with cheeses, olive oils, and handmade goods. With winding alleys, Renaissance churches, and sweeping valley views, Cortona invites you to slow down and savor la dolce vita.

Taste the Wines of Tuscany

Gather around the table for a guided tasting of four wines that define the region. From bold reds to elegant blends, each sip tells a story of the soil, climate, and centuries of winemaking tradition. Your host will guide you through aromas, textures, and pairings - making this not just a tasting, but an education in Tuscany's liquid art.

An Evening with a Private Chef

One evening, the flavors of Tuscany arrive at your doorstep. A private chef will prepare a 3-course dinner in your apartment, using ingredients sourced from local markets and family farms. As you savor each dish - handmade pasta, slow-simmered sauces, and rustic desserts - the chef shares the history and inspiration behind the recipes. With glasses raised and laughter echoing, it becomes more than a meal; it's a memory woven into the heart of Tuscany.

NOTE: 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.

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.

For all winning bidders, the Foundation's auction fulfillment manager will contact you within 24 to 48 hours after the event date to connect with you about shipping details. If the item is very small, a reduced shipping fee may be applicable.

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.

By participating in the Live Auction, you acknowledge that bidding is a voluntary action and, should you win an item, you are responsible for paying the full final bid amount.