Madrid was a Moorish frontier fort before it was a capital, and every layer since — Habsburg court, Bourbon palace, Napoleonic uprising, Civil War front line — is still legible in its stones. Three days, roughly chronological.
The oldest structure in Madrid: a 120-metre stretch of the ninth-century Islamic wall built under Emir Muhammad I, when the city was the frontier fort of Mayrit guarding Toledo. Open-air park on Cuesta de la Vega, accessible dawn to dusk.
Juana of Austria founded this convent in 1559 inside the palace where she was born; her sister-in-law and daughters of Spanish grandees took vows here, arriving with dowries of Titians and Brueghels. Guided visit only, roughly €6, closed Mondays.
Madrid's medieval civic heart. The fifteenth-century Torre de los Lujanes is the city's oldest surviving civil building, traditionally named as the prison of Francis I of France after his capture at Pavia in 1525. Casa de la Villa served as town hall until 2007.
The Jesuit church of 1622 that became Madrid's provisional cathedral for two centuries and still holds the incorrupt body of San Isidro Labrador, the twelfth-century farmhand-saint of the city. Free entry, generally 07:30-13:00 and 18:00-21:00.
Built 1738-1755 for Philip V after the Habsburg Alcázar burned on Christmas Eve 1734, taking Velázquez canvases with it. Europe's largest functioning royal palace at 135,000 m² and 3,418 rooms; Tiepolo ceilings and the Gasparini Room are the set pieces.
A genuine second-century-BC Nubian temple to Amun, gifted by Egypt in 1968 after Spanish engineers helped rescue Abu Simbel from the Aswan dam. Reassembled stone by stone on the Cuartel de la Montaña — the barracks stormed in July 1936.
Picasso's 1937 canvas, painted for the Spanish Pavilion in Paris weeks after the Condor Legion bombed the Basque town, hung in New York until 1981 and only came home after Franco's death. Room 205.06, in the old eighteenth-century General Hospital.
The 1768 post office whose clock rings in the new year became Franco's Dirección General de Seguridad, where prisoners were interrogated in the basement cells. The square also saw the 2 May 1808 rising against Murat's Mamluk cavalry.
Pedro de Ribera's 1721 Churrigueresque doorway fronts a former hospice, now the city's own museum: the 1656 Texeira map, the 1830 Model of Madrid by León Gil de Palacio, and the Bourbon urban plans that made the modern street grid.
Cervantes, Quevedo and Góngora lived within a few streets of each other here in the 1600s. Lope de Vega's own house on Calle Cervantes survives with its garden; Cervantes lies buried in the Trinitarias convent, identified only in 2015.
Goya frescoed this small 1798 chapel's dome with Madrid's washerwomen and street crowds instead of saints, and his headless body lies beneath it — the skull vanished before the 1919 reburial from Bordeaux. Free, closed Mondays.
The campus was the western front line from November 1936 to March 1939, fought room by room through the Clinical Hospital. Franco's 1956 triumphal arch still stands at Moncloa, and shrapnel scars remain on the Facultad de Filosofía walls.