Chinchón owns one of the most extraordinary squares in Spain: an irregular oval of three-storey houses laced with 234 wooden balconies, which has served as bullring, open-air theatre, film set and royal court since the 15th century — and still converts to all of them. Around it, a hill town of whitewash and garlic ropes distills the anís that carries its name across every Spanish bar shelf.
1. 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.
2. Anís tasting at the Alcoholera — Chinchón's aniseed spirit, dry or sweet, tasted where it's made — the copper stills date to 1911.
3. Iglesia de la Asunción's Goya — The parish church above the plaza keeps a Goya altarpiece — his brother was the priest here.
4. The castle & hermitage circuit — The ruined 16th-century castle and the hilltop hermitages give the classic panoramas over the plaza's rooftop oval.
5. 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.
Bus 337 from Madrid's Conde de Casal every 30–60 minutes (50 min). Drivers take the A-3 then M-404 (50 min) — combine with Aranjuez, 25 minutes west, for the classic vega day. No rail; that's the moat that keeps it quiet.
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