Island-hopping by public ferry rather than by tour — five islands in two weeks, chosen because they are different from each other rather than because they are famous.
Piraeus to Syros
Out of Athens on the morning ferry. Syros is the administrative capital of the Cyclades — a working town with an opera house, not a resort — and almost nobody stops here.
Syros
Ano Syros, the Catholic quarter on the hill, and the marble streets of Ermoupoli. The town was Greece's busiest port before Piraeus took over, and the architecture still says so.
To Naxos
Short hop south-east. Naxos is the largest of the Cyclades and the only one that could feed itself — it has real agriculture, which is why the food is better here.
Naxos interior
Rent something with wheels and go inland: Halki, Filoti, the marble quarries with their unfinished kouros statues lying where they cracked 2,600 years ago.
Mount Zas
The highest point in the Cyclades, three hours up and back from Filoti, with the whole archipelago laid out at the top. Start early — there is no shade above the tree line.
Naxos beaches
The west coast runs a long chain of them — Agios Prokopios, Plaka, Alyko. Plaka is four kilometres long and you can still find it empty in the shoulder months.
To Amorgos
The long way east to the edge of the group. Check the timetable carefully — the connection runs a few times a week, not daily, and missing it costs two days.
Hozoviotissa
The monastery built into a cliff face 300 metres above the sea, occupied since the 11th century. Modest dress, and they give you a glass of psimeni raki at the top whether you want one or not.
Amorgos on foot
The old footpaths between villages are waymarked and largely empty. Chora to Aegiali is the classic, four hours along the spine of the island.
Back west to Folegandros
A connection day. Folegandros is small, steep and quiet, and its Chora sits on a cliff edge that does the Santorini job without the Santorini crowd.
Folegandros
Walk up to Panagia church for the evening, swim at Agali, eat in the square. There is not much to do and that is what people come for.
To Milos
Milos is a volcanic island that looks like several different planets — Sarakiniko is white rock scoured into shapes, Kleftiko is only reachable by boat.
Milos by boat
A full-day boat around the island is the only way to see most of its coast, and it is worth the money. Book the small operators, not the big catamaran.
Back to Piraeus
The long ferry home, or fly out of Milos if the timing is tight. Deck class one last time.
Good to know
Ferry timetables for the following summer are published in stages from around February and change; do not book a rigid chain of islands more than a few days ahead. Deck class is fine in summer and about a third of the price of a fast boat — Greeks use it. In July and August book accommodation early and expect to pay double. Wind is the real variable: the meltemi blows hardest in July and August and cancels boats, which is another argument for June or September.
Shorter or longer?
Swap Milos for Koufonisia, Schinoussa and Iraklia — tiny, connected by a local ferry, and about as quiet as the Aegean gets in summer.
Naxos for two weeks. Mountains, villages, beaches and enough food to justify it, without spending four days of the trip on boats.