Planning a trip to the Greek Islands
Greece rewards flexibility. The high season runs from late May to early September, when the Aegean is warm, the ferries run on the hour, and the meltemi wind keeps the heat honest. Everything works — but everything is busy.
If you can travel outside school holidays, May and September are the sweet spot. You get beach weather without the crush; tavernas have time to chat; and you can usually walk into a hotel with no reservation.
Winter on the islands is a different story. Most of Santorini and Mykonos closes down from November to April. The exceptions are Crete and Rhodes, which stay open year round and are a revelation in February — empty archaeological sites, mild afternoons, and wild flowers on the coast roads.
For a first trip, Santorini plus Naxos makes a good pair: one iconic, one working. For a third or fourth trip, try the Dodecanese — Symi, Kastellorizo, Tilos — where you'll need a ferry timetable and a bit of Greek.