Stay in one of two historic, carefully curated apartments with breathtaking rooftop views. 

Two Queen ensuite bedrooms perfect for two couples or a small family. 

Walk the cobblestone streets of Cortona with a private guided tour included in your stay. 

Sample the area's varietal with a complimentary wine tasting. 

Winner receives a trip for seven nights to Cortona Italy. Four guests are accommodated with two bedrooms and two bathrooms. Winner has twelve months to book and 24 months from event date to travel, with access to Premium Guest Services for trip planning. Airfare not included. Travel year-round with the exception of Thanksgiving, Christmas, and New Year weeks.