No advice on wineries, but some suggestions on Toledo:
Restaurants in Toledo
La Abadia (
www.abadiatoledo.com) - a favorite of mine and of my family that lives in Toledo
Locum
Hierbabuena -- amazing views, located on the Circunvalacion del Valle
Very traditional -- Adolfo, Casa Aurelio, Hostal del Cardenal
Sights
Catedral
Alcazar
Puente de San Martin
Puente de Alcantara
Puerta de Bisagra
Mezquita Cristo de la Luz
Hospital de Santa Cruz
Monasterio San Juan de los Reyes
Sinagoga del Transito
Sinagoga de Santa Maria La Blanca
Museo del Greco
Museo del Ejercito
Plaza de Zocodover
Sweets -- must get some Mazapan - Santo Tome is most famous
Walk the Circunvalacion del Valle (or run it if you are a runner)
A couple nice spots for drinks
Picaro
Virtudes Caffe Bar & Music
El Trebol
Keep in mind for driving that the streets are VERY narrow!!