Discover ancient culture, magnificent art, delicious gastronomy and breathtaking landscapes, all in one place! Escape from the mundane and immerse your selves in the simple pleasures of Tuscany, Italy.

Spend 7-nights (Saturday to Saturday stay) in the heart of Tuscany, in one of our stunning 4 bedroom/4 bath Villas with a private pool. The Villas in our collection are located throughout the Tuscan countryside and close to the famous hilltop town of Cortona.

During your stay, you will select one day to enjoy a fabulous lunch at a winery with wine pairings, preceded by a visit to the vineyard and cellar (transportation not included, but can be arranged).

One evening, you will also take part in a fun and enjoyable cooking class right in the comfort of your Villa, learning the secrets of fresh home-made pasta, mouth-watering sauces, Tuscan meat dishes and desserts, all from a local Chef. The class will be followed by a delicious dinner.

Hear from last year's winner:
Christine and her husband, Dave, won this incredible Tuscany adventure at Mad Hatter and returned from the trip just this past July. "The Tuscany villa was absolutely wonderful and well-equipped. Manciano is a quaint town just 30 minutes from the sea and equally close to fantastic wineries and restaurants. One of our favorite parts of the villa experience was spending time in the town, where the community gathers each night in the square to socialize, enjoying great food, wine, and the best gelato we’ve ever had!" 

Note: Tuscany is 200 miles north of Rome, approximately 4 hours by car or 3 hours by train.

Blackout Dates: All major holidays, special events and additional dates may apply.