This trip started on a cruise and ended in Athens, with 10 days in between hopping the Cyclades on our own. We’d been to Greece before, briefly, but never to any of the islands chain. We went in early May — deliberately off-peak — and found a version of Greece that was sometimes chilly and occasionally frustrating, but mostly exactly what we’d hoped for.
The Cyclades are one of the major island chains of Greece, centrally located as opposed to the Ionian islands (nearer Venice in the north of Greece) or the Dodecanese (off the coast of Turkey). The islands share dry, rocky, and wind-scoured landscapes, but are not all the same.
That sounds obvious and it isn’t. Santorini is spectacle — arguably the most visually extraordinary place either of us has been — but it has surrendered almost entirely to tourism. Paros feels like a place where actual Greeks still live. Milos is sleepy in a way that rewards slower travelers and defeats impatient ones. Naxos, which we only saw for 6 hours, made us wish we’d rearranged more of our itinerary around it.
We almost skipped Naxos entirely. It was a 6-hour stopover on the way to Paros. It became the island we most want to return to.
We ended in Athens with 3 nights and not enough time. Go figure.
How the Trip Was Structured
We did a 10-day cruise from Barcelona to Athens before this trip, and leave that out of this summary. The cruise line provided transport to Athens airport. From there we flew to Milos and worked our way east and north before finishing in Athens:
Athens → Milos → Santorini → Naxos (6 hrs) → Paros → Athens
We did 3 inter-island ferries and 2 flights. The ferry overhead is real, and we’d caution against cramming in more than we did. That said, we also fit in Naxos, Delos, Mykonos, and Antiparos as day trips without re-packing, which is worth knowing.
Before you dive into the island pages, start with our Tips page — ferry logistics, what May actually feels like, and what we learned about eating and drinking across the Cyclades.
Our Verdicts
| Location | Verdict | Why |
|---|---|---|
| Milos | Glad We Went | Lovely and low-key; better in summer when beaches open |
| Santorini | Would Plan Around | Spectacular; crowded; stay multiple nights for the sunsets |
| Naxos | Wish We’d Stayed Longer | 6 hours was a mistake; go back |
| Paros | Would Plan Around | Best home base in the Cyclades |
| Delos | Glad We Went | Remarkable ruins; get a guide |
| Mykonos | Glad We Went | 3 hours confirmed why people love it |
| Athens | Would Plan Around | 3 nights minimum; Acropolis at sunset with a guide |
Greece rewards travelers who resist the urge to see everything. The overhead of moving between islands is real — but 5 nights in Paros let us do day trips to Delos, Mykonos, and Antiparos without touching our luggage. The places that surprised us most — Naxos, the marble village of Apeiranthos, the Mycenaean room in Athens — were ones we almost skipped.
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