Santorini & Milos, Greece
Two islands, one boat between them, and the caldera at golden hour without the cruise-ship crush.
Most Santorini trips are a queue with a view. This one isn't. You stay in Imerovigli rather than Oia, which puts you fifteen quiet minutes from the crowds and gives you the same caldera from a terrace nobody is fighting you for.
Day four you take the morning ferry to Milos, which is where Greece stops performing and starts being lived in. Sarakiniko at 7am is lunar and empty. The fishing villages still fish. You'll eat better here than anywhere on Santorini, for a third of the price.
We put a private sunset sail on the last Santorini night because it's the one splurge that's genuinely worth it — you get the caldera from the water while everyone else is three deep on a wall in Oia.
Met at the airport, transferred to Imerovigli. Nothing scheduled — the terrace and an early night is the right call after the flight.
Walk Fira to Oia along the rim in the morning while it's cool. Afternoon free. Dinner in Imerovigli, away from the Oia scrum.
Private catamaran from Ammoudi at 4pm — hot springs, Red Beach, dinner cooked aboard as the sun goes down behind the volcano.
Morning ferry, arriving Adamas by noon. Check into a harbour-front room, then a slow afternoon in Plaka for the sunset over the bay.
Early start, and worth it — white volcanic rock with nobody on it. Back for breakfast, then Kleftiko by boat in the afternoon.
Klima, Mandrakia, Firopotamos — three syrmata villages, an unhurried lunch, and a swim wherever you feel like stopping.
Nothing booked. Most people hire a quad and get lost, which is the correct answer.
Ferry or direct flight out of Milos depending on your onward routing.