Imagine strolling cobblestone streets at golden hour, the rooftops of Cortona glowing in the late-day light as church bells echo across the valley. In every direction, vineyards and olive groves roll toward the horizon, while the scent of freshly baked bread and simmering sauces drifts from nearby trattorias. For four lucky guests, this is Tuscany not as a tourist sees it, but as a local feels it - intimate, authentic, and unforgettable.
Stay in the Heart of Cortona!

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.

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.

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.

Your choice of a three (3)-night weekend (Fri-Sun) or four (4)-night weekday (Mon-Thu) stay in Tuscany for four guests.

Blackout dates may apply; travel must be booked within one year of winning.