Three Cultures Quixote Tour (Toledo - Cuenca) (2 Nights)
Day 1 - Tour of Toledo
Transfer from Madrid to Toledo, where you will have an expertly guided walking tour of the beautiful, walled city. See the architectural and artistic influence of the 3 cultures that have lived here in harmony as you walk through the town's narrow, cobbled streets. See the city's sites, such as the Cathedral, Alcazar, Synagogues and beautiful gates the area is famous for. Spend the night in the Parador de Toledo, with the best views of the city.
Day 2 - Visit the Quijote Windmills and their Museums
Transfer to Campo de Criptana, where you will visit the Quijote Windmills - famous for their portrayal in the novel "Don Quixote" and named a Cultural Heritage Site in 1978. Tour the small museums inside the windmills that honor wine, working the ground, poetry and people. One of the windmills even houses the local office of tourism. Every Saturday you can see one of the renovated windmills in operation. After the tour, you will be transferred to Cuenca, spending the night in the Parador de Cuenca, facing the city's canyons and hanging houses. 
Day 3 - Walking Tour of Cuenca and Spanish Wine Tasting
Take a walking tour of Cuenca, named a UNESCO World Heritage City. Placed between the Jucar and Huecar river canyons, see the city's beautiful views, hanging houses, cobbled streets and Cathedral. On the way back to Madrid, stop for a tasting of local Spanish wines.