Cyclades
Cyclades in Eight Days
Three islands, two ferries, and enough time on each to stop checking the schedule.
From $2,150pp
8 datesJournal · September 11, 2026
By Leo Shim

Every island week we run has three ferry crossings in it, and every one of them has the same rule: we do not book the tight connection.
The timetable will tell you the 14:05 from Paros meets the 15:20 onward to Naxos with time to spare. It does, on paper. In August, with a meltemi blowing, the 14:05 leaves at 14:40 and arrives when it arrives. The people on the tight connection are the ones on the quay with their luggage watching the second boat leave.
Sit outside. The inside of a Greek ferry is a television and a queue for the toilets; the outside is the reason you came. On the Paros–Naxos leg, stand at the back rail on the left side about twenty minutes in and watch Naxos arrive with the Portara standing on its islet like a doorway to nothing.
The islands are not a list to be completed. They are a rhythm to be caught.
That line is from Yannis, who has run our Cyclades weeks for six years. It is the closest thing we have to a company motto.
Buy the ferry ticket the morning you leave, not the night before. Plans change, weather changes, and a paper ticket for a boat you have decided not to take is a small, avoidable sadness.
The full route, with the two-night minimums built in, is Cyclades in Eight Days.
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