Morning
Plaza Mayor from a balcony. Order lunch at a mesón's first-floor balcony table and watch the square perform below — the theatre hasn't changed in four centuries.
Anís tasting at the Alcoholera. Chinchón's aniseed spirit, dry or sweet, tasted where it's made — the copper stills date to 1911.
Afternoon
Balconies, castle & the anís lanes — 3 km · 1.5 h. Plaza Mayor → Iglesia de la Asunción → the castle ruin's viewpoint → down through the whitewashed lanes past the Teatro Lope de Vega → the Alcoholera for a tasting. Short, steep in bursts, and best at golden hour.
Iglesia de la Asunción's Goya. The parish church above the plaza keeps a Goya altarpiece — his brother was the priest here.
Evening
The castle & hermitage circuit. The ruined 16th-century castle and the hilltop hermitages give the classic panoramas over the plaza's rooftop oval.
Sleeping here? Sleeping on the Plaza Mayor itself — several small hotels occupy the balconied houses — is the whole point; book months ahead for weekends. The parador in the old convent is the luxurious alternative, one minute uphill. Weeknights the town is nearly private.
Questions, answered
Where to sleep: Chinchón
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