Five nights in Santorini for the version of Greece you already had in your head & five nights in Milos for the version you didn't know to ask for. This is the itinerary I keep coming back to (and the one I'd tell my best friend to book tomorrow). Private pool villas, catamaran days, a moon beach, incredible food, and what to skip.

Peak season sells you the version of a place everyone else already has. Shoulder season gives you the one nobody's fighting you for; empty trails, five people at the Trevi Fountain, business class for the price of economy. This isn't the compromise trip. It's can just be the smarter one.