If you have one week, do not chase all seven. Choose by route. For the easiest ferry planning, start with Naxos and add Amorgos or Folegandros. For a quieter nature trip, fly or ferry toward Rhodes and spend real time on Tilos. For waterfalls and hiking, make Samothraki the destination, not a detour. For an island that feels like a small country with its own internal logic, rent a car on Kythira and slow down.
The biggest hidden cost in Greece is not always the ferry ticket; it is a bad sequence. A cheap room becomes expensive if the only boat leaves at dawn, arrives after midnight, or forces you to backtrack through Athens. Before booking hotels, check ferry days, match island groups, and leave one flexible night before international flights.
For most travelers, June and September are the sweet spots. The sea is swimmable, the best tavernas are open, and the islands still have enough life without August prices. If you travel in shoulder season, confirm buses, ferries, and car-rental hours a few days before arrival. That tiny bit of admin is what makes off-path Greece feel easy.