Singapore’s 1985 covered linkway scheme — the one most often misattributed to Lee Kuan Yew personally — required every new commercial development along Orchard Road to provide a continuous covered pedestrian walkway across its frontage, of a minimum width and clear height, that connected to the neighbor on either side. Forty years later the result is one of the few stretches of urban street anywhere on earth where you can walk a mile and a half in equatorial midday sun without ever stepping into direct light. The cover is sometimes a building canopy, sometimes a glass arcade, sometimes an underground link through a mall basement. The Stay Cool router treats all of them as building shade and grades them at 95%.
The picks below stitch the run. They are short — the point is the stitch, not the distance — and they assume you are willing to dip into a mall basement when the geometry calls for it. A note on the few gaps: the pedestrian crossings at Scotts and at Cairnhill are open. Carry an umbrella for those thirty seconds; everyone here does.