Everyone knows Santorini and Mykonos. They are spectacular, and they are also expensive, crowded, and – during July and August – an exercise in competitive queueing. The Cyclades have 24 inhabited islands. Most visitors see two of them.
I spent a month hopping between six of the others. The ferries were cheap, the beaches were empty, the food was extraordinary, and at no point did I have to elbow a stranger for a photograph. Here is the route.
Week 1: Serifos
Serifos is the island that Cyclades veterans recommend to each other in whispers, as if speaking its name too loudly might summon the crowds. It has not happened yet.
The chora (main town) sits on a hilltop above the port, a tumble of white cubes and blue shutters that looks exactly like the postcards of Santorini but without the four million annual visitors. The climb from Livadi harbour to the chora takes 30 minutes on foot and provides the kind of cardiovascular workout that justifies the evening’s second portion of grilled octopus.
The beaches are Serifos’s real draw. Psili Ammos on the south coast requires a 20-minute walk down a goat path and rewards you with golden sand, turquoise water, and maybe three other people. Ganema and Vagia on the north coast are accessible by dirt road and feel like private coves.
The island has one ATM (in Livadi), limited Wi-Fi outside the port area, and a pace of life that makes you reconsider your entire relationship with urgency. A room costs EUR 40-70 per night in September. Meals at the port tavernas run EUR 10-15 per person including wine.
Week 2: Sifnos
The ferry from Serifos to Sifnos takes 40 minutes and costs under EUR 10. Sifnos is the food island of the Cyclades – not in the Michelin-star sense, but in the sense that the local cooking tradition here is deeper and more distinctive than anywhere else in the archipelago.
The island’s signature dish is revithada – chickpeas slow-baked overnight in a clay pot. Every taverna serves its own version. The best I had was at a place in Artemonas where the owner’s grandmother was still making it using a recipe that predated electricity on the island.
Sifnos has better infrastructure than Serifos – reliable Wi-Fi, several ATMs, a proper road network – without losing the small-island feeling. Kastro, the old fortified village on the east coast, is one of the most atmospheric settlements in the Cyclades: medieval walls, narrow passageways, and a church built into the cliff face overlooking the sea.
The hiking is excellent. A network of old stone paths (monopathia) connects the villages, and walking from Apollonia to Kastro via Artemonas takes about two hours through a landscape of olive groves, churches, and dry-stone walls.
Week 3: Folegandros
Folegandros is the island that travel writers describe as “what Santorini was thirty years ago” – which is both accurate and the kind of thing that will eventually ruin it. For now, though, it is still perfect.
The chora is built on the edge of a 200-metre cliff. The main square – with its three churches, two cafes, and one enormous tree – is where the entire island seems to gather every evening. The social ritual of the volta (evening walk) is alive and well here in a way that feels unforced rather than performative.
The beach at Agali is the best on the island – a crescent of coarse sand accessible by bus or a 30-minute walk from the chora. The beach tavernas serve grilled fish that was swimming an hour before it reached your plate.
Folegandros is deliberately undeveloped. There is no airport. The ferry from Piraeus takes around six hours (or three from Santorini). The road network amounts to one main road connecting the port, the chora, and Ano Meria village. This is by design – the island’s small permanent population (around 750) has consistently resisted the kind of development that transformed their more famous neighbours.
Budget EUR 50-90 per night for accommodation in September. The island books out in August, so avoid that month unless you plan months ahead.
Week 4: Milos, Kimolos, and Koufonisia
I split the final week between three islands, which is ambitious but possible with good ferry timing.
Milos is the geological outlier of the Cyclades – volcanic rather than limestone, which gives it a coastline of surreal rock formations, multicoloured cliffs, and sea caves. Sarakiniko, with its lunar white rock formations sculpted by wind and water, is one of the most photographed beaches in Greece. It deserves every photograph.
The island has over 70 beaches, which means that even in peak season you can find one to yourself if you are willing to drive a dirt road or walk a coastal path. Kleftiko, accessible only by boat, is a cluster of sea caves and rock arches where pirates allegedly hid their ships. The boat trip from Adamas takes half a day and is worth every euro.
Kimolos is a 20-minute ferry from Milos and receives a fraction of its visitors. The main village has one small hotel, a handful of rooms to rent, and a genuinely warm welcome from residents who are pleased but slightly bewildered by the occasional tourist. The hot springs at Prassa beach are accessible by a short walk and have been used since antiquity.
Koufonisia (specifically Ano Koufonisi, the inhabited one) is tiny – you can walk across it in 45 minutes. The beaches on the south coast are reached by a coastal path that passes through natural rock pools, small coves, and formations that look like abstract sculpture. In September, the island has the quality of a daydream.
The Practical Bits
Getting there: Ferries from Piraeus (Athens port) serve all of these islands. Blue Star Ferries and SeaJets are the main operators. Book through Ferryhopper or directly with the operators. High-speed ferries are more expensive but cut travel times significantly.
Island-hopping logistics: Not all islands connect directly to each other. The hub-and-spoke model works: Piraeus to your first island, then short hops between neighbouring islands, then back to Piraeus from the last one. Check connections carefully – some routes only run a few times per week.
When to go: September is the sweet spot. Water is warm (24-25C), crowds have thinned, prices drop, and the light has a golden quality that photographers chase.
Budget: EUR 50-100 per night for a decent room, EUR 10-18 per meal at a taverna, EUR 5-15 per inter-island ferry. A month-long trip including flights can be done for EUR 2,500-3,500 per person.
Useful Resources
- Ferryhopper – Real-time ferry schedules and booking across all Greek islands
- Visit Greece – Official tourism board with island profiles and event calendars
- Wikiloc – Hiking trail maps for all Cycladic islands
- Greece residency options – For those considering an extended or permanent stay beyond the tourist season (source)
- Greek Gastronomy Guide – Regional food traditions by island and region
