Taste of Tuscany included
Discover the region's culinary delights with a private winery tour, tasting, and cooking class.
Tuscany
Timeless Tuscany
- 8 Guests
- 7 Nights
- 4 Bedrooms
- 3 Bathrooms
Timeless Tuscany
Step into a timeless Tuscan dream with a seven-night stay in one of five centuries-old villas in the Cortona hillside.
Discover the region’s culinary pleasures with a private winery tour, tasting, and cooking class included for all guests.
Discover charming medieval towns and renowned works of art with a bespoke itinerary crafted by your travel experts.
Escape to the Tuscan countryside for seven nights in one of five picturesque Italian villas.
- Stay in a carefully curated historic home, with private pool and courtyard
- Enjoy a private winery tour and cooking classes included for all guests
- Discover world-famous art and architecture with a bespoke travel itinerary
- Explore the region with day trips to Cortona, Montepulciano, and Arezzo
- Benefit from Premium Guest Services for trip planning
Terms and Conditions
- Winners have 12 months from the purchase date to confirm their reservation and up to 24 months from the purchase date to travel.
- Subject to availability and travel Saturday to Saturday year-round with the exception of Thanksgiving, Christmas, and New Year weeks. Please inquire for details.
- Please note, images displayed depict multiple villas. Villas are allocated according to availability. No specific villa is guaranteed, and exact bedroom/bathroom configuration may vary.
- Please see your winner certificate for full terms and conditions.
Get to know Tuscany
Sweeping vineyards, rolling hills, and picturesque medieval towns set the romantic backdrop for Italy’s famed Tuscany region. With a rich history spanning the Roman and Renaissance eras, 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 four stunning bedrooms.
Outside, winding gardens and sun-dappled courtyards give 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.
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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 the sun-drenched piazzas and panoramic views of this picturesque region.
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 four stunning bedrooms.
Outside, winding gardens and sun-dappled courtyards give 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 the sun-drenched piazzas and panoramic views of this picturesque region.
Handpicked local experiences
Day Trip with Private Driver optional
Explore the surrounding area at your own pace with a private driver, discovering local highlights and hidden gems along the way.
Private Chef Dinner optional
Savor the delicacies of the region with a gourmet dinner prepared in your accommodation by a private chef.
Housekeeping optional
Enjoy a seamless stay with a professional cleaning service, keeping your accommodations fresh and inviting.
Bedroom configuration
- Bedroom 1: Double size bed · Private bathroom
- Bedroom 2: Double size bed · Private bathroom
- Bedroom 3: Double size bed · Shared bathroom
- Bedroom 4: Double size bed
Amenities available to you
AC
Washer
Wireless internet
Dishwasher
Pool
Bbq area
Patio or balcony
Garden or backyard- Cleaning before checkout
Rural
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- AC
- Washer
- Wireless internet
- Dishwasher
- Pool
- Bbq area
- Patio or balcony
- Garden or backyard
- Cleaning before checkout
- Rural
Location on Map
Tuscany, Italy
Enjoy our world-class
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Our Signature Collection comes with Premium Guest Services to transform your donors' vacations into once-in-a-lifetime experiences. From white-glove trip planning to exclusive amenities and services, we deliver stays that are as seamless as they are exceptional.
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All our travel experiences are customizable to the needs of our guests. Extended dates, upgraded homes, and additional services are all available upon request.Since you're interested in Italy
