Heidelberg pairs a ruined hilltop castle with one of Europe's longest pedestrian shopping streets, the whole scene framed by the Neckar River and the wooded slopes of the Heiligenberg.
Late spring or early autumn on a clear afternoon, when the light on the castle's red sandstone is best from the Alte Brücke and the Philosophenweg isn't crowded with summer tour groups.
Order a Studentenkuss ("student's kiss") — a chocolate-wrapped praline sold since the 1860s at a confectionery on the Hauptstraße, invented so university students could flirt with the shop's customers without their chaperones noticing.
Base yourself near the Marktplatz or lower Hauptstraße, within a flat walk of the Old Bridge and the path up to the castle.
Walk up to the castle rather than taking the funicular, then ride the funicular back down to the Kornmarkt — the uphill path through the Old Town gardens is free and better for photos than the queue for the train.
Read more in Heidelberg Travel Guide: Castle Ruins & the Neckar River.