Toledo
Medieval hilltop city — synagogues, mosques, churches, El Greco
Madrid's central position + Spain's AVE high-speed rail means Toledo, Segovia, Cuenca, and even Seville (long) are day trips.
Medieval hilltop city — synagogues, mosques, churches, El Greco
Roman aqueduct + Disney-castle Alcázar + suckling pig at Mesón de Cándido
Spain's biggest monastery complex — built by Felipe II
Hanging houses on a cliff + abstract art museum
Royal palace + gardens + strawberry train (in season)
Long but doable — Real Alcázar + cathedral + tapas in Triana