The Storied Heart of Italy
Sweeping vineyards, rolling hills, and picturesque medieval towns set the romantic backdrop for Italy’s famed Tuscany region. With a rich history spanning Roman and Renaissance, this breathtaking region weaves together some of Europe’s finest art, culture, and cuisine with a love of life’s simplest pleasures.
Experience the art of Tuscan living the moment you set foot in your historic Italian villa. Nestled in the rolling hills of Cortona and surrounded by the sweet smell of cypress trees, your Tuscan retreat features a rich blend of rustic tradition and contemporary luxury. Arched windows, cathedral wood ceilings, and centuries-old stonework capture an elegant simplicity that is carried over into three stunning bedrooms.
Outside, winding gardens and sun-dappled courtyards look out over the sweeping hills and valleys, inviting afternoons of alfresco dining and refreshing dips in the sparkling waters of the private pool. For a true taste of Tuscany, indulge in an exploration of the region’s culinary treasures with a private winery tasting tour and lunch. Then discover a world of gourmet flavor with a private cooking class and dinner, all included in your stay.
The nearby medieval towns of Cortona, Montepulciano, and Arezzo call for days of leisurely exploration. Discover ancient architecture, medieval frescoes, and timeless Renaissance masterpieces with a bespoke itinerary crafted by your travel experts. Or simply lose yourself in this picturesque region's sun-drenched piazzas and panoramic views. With 7 nights for 6 people, it's truly the perfect Italian escape for families and couples alike.
- 7 nights, 6 days in a stunning Italian countryside villa
- 3 bedrooms, 3 bathrooms accommodate up to 6 people
- Views of rolling hills and wide-spanning vistas
- Tuscan cooking class and dinner
- Tuscan winery lunch, private visit & tasting*
- A private pool and luxury accommodations
- Nearby charming Cortona
- Personalized booking and concierge services
- Bedroom 1: Double bed with en suite bathroom
- Bedroom 2: Double bed with private bathroom
- Bedroom 3: Double bed with adjoining bathroom
The winner has 12 months to book and 24 months to use. Subject to availability. Nights must be used during one stay. Primary guest must be at least 25 years of age. If property, activity, or service is no longer available at the requested time of stay, a substitute property, activity, or service of equal or greater value will be provided. The provider is not liable for providing alternative accommodations if the preferred travel dates are unavailable. Blackout dates are the weeks of Christmas and New Year. This experience includes a stay at one of four 3-bedroom villas based on availability at the time of booking. Upgrades are available upon request.