A long weekend in the Cyclades can be enough for a first taste, provided you commit to a single island. Mykonos is well-suited to short stays: the Chora can be walked in a morning, the best beaches are 20 minutes away, and the nightlife will fill the evenings. Santorini also rewards a long weekend — three nights minimum — long enough to spend a day in Oia, half a day at Akrotiri and one classic caldera cruise.
For one week in the Cyclades, the classic combinations are Santorini–Paros–Mykonos or Santorini–Naxos–Mykonos, with two to three nights on each island. From Santorini, reaching Paros (around three hours on the high-speed ferry) and then Mykonos (90 minutes from Paros) makes a smooth loop, well served in season. That rhythm lets you compare Santorini's volcanic theatre, Parian ease and Mykonos's cosmopolitan energy without ever feeling rushed.
A 10- to 15-day trip opens the door to lesser-known Cyclades. After ticking off the headline islands, you can fold in Naxos (two nights — hiking through mountain villages), Folegandros (two nights — a perched Hora and intimate village life) or Amorgos (two nights — beautiful coastal walks and the cliffside Monastery of Hozoviotissa). An itinerary running Athens–Santorini–Folegandros–Naxos–Paros–Mykonos–Delos–back to Athens covers a week and a half coherently, following the natural ferry lines of the archipelago.
Depending on your style, the Cyclades break down into several flavours of trip. Couples on a romantic break will lean towards Santorini and Folegandros. Families do well on Naxos: large, affordable, with long, safe sandy beaches. Party-seekers and solo travellers gravitate to Mykonos and Ios. And those chasing a more authentic Greece are best served by Sifnos, Serifos or Syros. In all cases, build in a little flexibility — the Cyclades are best enjoyed when you can shrug off the missed ferry and reach for another carafe of wine.
A final tip for building any Cycladic itinerary: book the structural ferries first, then your accommodation, and try to keep your final night on an island with an airport or a strong Piraeus connection. Summer winds — the famous Meltemi — can delay crossings. Adding one buffer day before any onward flight will spare you a lot of stress. Treated this way, hopping between Cycladic islands becomes a pleasure rather than a logistical chore.