Santorini

This is the one I would hand you if you were going to Santorini and wanted to do it properly: where to stay village by village, where to eat now that the island has stars, which day trips earn their place, and the handful of things I would quietly skip. It is long on purpose. Santorini rewards a bit of planning more than almost anywhere I work, because the difference between a good trip here and a wonderful one is almost entirely in the sequencing.

Four nights is my minimum and five is better. The island is small enough to see in that time and interesting enough to fill it, and the extra day gives you something to trade if the wind takes a boat day away from you.