Reguliersgracht
Give the first evening to a walk that looks like a romantic stroll and is in fact reconnaissance. Three places do most of the work in this city, and they are all within half an hour of each other on foot.
The first is the Reguliersgracht crossing at the Herengracht, where you look down a line of seven arched bridges, each outlined in lights and reflected in the water. It is the most spectacular free view in Amsterdam after dark and, because it is a photograph everyone takes, the most likely to have other people on it. The second is the Magere Brug, the white wooden drawbridge over the Amstel that is picked out in small lights at night — wider, calmer, with proper standing room away from the traffic lane. The third is the corner where the Brouwersgracht meets the Prinsengracht, beside Café Papeneiland, which is quieter than either and is regularly called the prettiest spot in the city by people who live here.
Walk all three at roughly the time of evening you are considering, and pay attention to the boring things: how many people are standing there, where the bikes come from, whether there is a bench, whether the wind is coming down the water. Then pick one and a fallback, and stop thinking about it.
Reguliersgracht
Photo: WJ NWS