LIKING LEEWARDS: Taking islands as a worldly whole, most sport a windward and leeward side. The lee side is frequently where the fun is, so to speak. Cities take shape thereabouts due to, well, their leewardness, meaning calmer conditions and more protected portage. The oft nasty old windward sides of islands have no problem living up to their rough-guy image, trending toward a more grizzled windblown look and feel.

But what happens when an island is remarkably long and narrow, residing in a north-to-south direction, alluding to East…