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Timeless Tuscany

Escape to the picturesque hills of Tuscany with a stay in one of five authentic Italian villas with wine tasting tour and cooking class.

8 guests
7 nights
4 beds
3 baths
See photos

Timeless Tuscany

8 guests
7 nights
4 beds
3 baths

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
Need to Know
  • 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.
  • One-of-a-kind curated destinations
  • Premium Guest Services for trip planning
  • Professionally-managed properties
  • Personally vetted homes for the highest standards of quality

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 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.

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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.

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:

check icon Ac
check icon Washer
check icon Wireless internet
check icon Dishwasher
check icon Pool
check icon Bbq area
check icon Patio or balcony
check icon Garden or backyard
check icon Cleaning before checkout
check icon Rural

Anything you need that’s not listed here?

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Location on Map Tuscany, Italy

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Enjoy our world-class

LuxGive Hospitality

Enjoy five-star amenities and service.

Our winners benefit from Premium Guest Services for an unparalleled vacation experience. From access to the world's finest properties to a vast portfolio of luxury services and activities, we're committed to delivering seamless and unforgettable stays.

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Immerse yourself in our

Handpicked Local Experiences

Your trip doesn't end with accommodation. We've handpicked some of the best local experiences in the area, so you can spend less time planning and more time making memories.

Taste of Tuscany

Discover the region's culinary delights with a private winery tour, tasting, and cooking class.

Optional: Florence Day Trip with Chauffeur

Discover Florence, capital of Tuscany and home of the Renaissance, with a chauffeur-driven day trip to Florence and surrounding hilltop towns. Acquaint yourself with la dolce vita and explore all beautiful Tuscany has to offer.

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Final Notes:

At LuxGive, we believe in delivering once-in-a-lifetime experiences worthy of donors’ generosity.

All our travel experiences are customizable to the needs of our guests. Extended dates, upgraded homes, and additional services are all available upon request.

Inquire for more details