A week-long private yacht charter through the Cyclades is the definitive Greek islands experience. This 286-nautical-mile route links six islands and Cape Sounio in a circular loop from Athens, balancing cosmopolitan harbours with quiet anchorages and some of the Aegean's most recognisable landscapes.
Your VoyageAthens to Kea
The closest Cycladic island to Attica, Kea rewards early departures with quiet anchorages that the day-trip crowds never reach. The port of Korissia sits on the site of an ancient settlement; the town walls and a Sanctuary of Apollo are still visible. Inland, the 6th-century BCE Lion of Kea — carved directly from the rock on a hillside above Ioulis — is one of the oldest monumental sculptures in Greece. For an evening swim, anchor in Poleis Bay on the northwest coast. Vourkari, a short walk from Korissia, has a clutch of good waterfront tavernas.
Kea to Syros
A 48-nm passage east to Ermoupoli, the administrative capital of the Cyclades and one of the finest neoclassical harbour towns in the Mediterranean. The approach alone — Ermoupoli rising in tiers around the bay, crowned by two hilltop churches — sets the tone. Ashore, the town has a grandeur that feels more Trieste than typical Cycladic white-and-blue: marble squares, a municipal theatre modelled on La Scala, and the Vaporia quarter with its painted sea-captains' mansions. Good anchorages elsewhere on the island include Vari in the south and Kini on the west coast. Syros is known for its loukoumi (a local Turkish-delight variant) and a strong summer cultural programme.
Syros to Mykonos
A short 20-nm hop to the most recognisable island in the Aegean. Mykonos needs little introduction: the windmills above Chora, the labyrinthine streets of Little Venice, and a nightlife scene that runs until dawn. The old port and the new marina at Tourlos both offer berths, though high-season demand is intense — confirm arrangements in advance. Beyond the town, the south coast beaches (Psarou, Platis Gialos, Ornos) are well-serviced, while the north side offers more sheltered anchorages when the Meltemi is up. A half-day excursion to the archaeological site on Delos (UNESCO World Heritage) is highly recommended — boats depart from the old port.
Mykonos to Paros
Thirty-two nautical miles south to Paros, an island that balances Cycladic authenticity with a well-developed visitor infrastructure. The main port of Paroikia has the 6th-century Panagia Ekatontapyliani (Church of a Hundred Doors), one of the most important Byzantine monuments in Greece. On the north coast, Naoussa — once a quiet fishing village, now a sought-after destination in its own right — sits around a Venetian harbour. Paros is also one of the Aegean's top windsurfing locations; the channel between Paros and Naxos funnels reliable afternoon winds. Overnight options include Paroikia harbour, Naoussa, or the quieter anchorage at Kolimbithres.
Paros to Sifnos
A 36-nm sail west to Sifnos, widely considered the gastronomic capital of the Cyclades. The main port of Kamares is well-protected and sits beneath dramatic hillsides. Inland, the medieval village of Kastro — perched on a cliff with remnants of ancient walls — offers one of the best vantage points in the island group. The bays of Vathi, Faros, and Platis Gialos are worth exploring by tender: turquoise water, good snorkelling, and waterfront tavernas serving local specialities. The best dining is concentrated in Apollonia, the island's main town.
Sifnos to Kythnos
Thirty-seven nautical miles north to one of the most unspoiled islands in the western Cyclades. Kythnos has a deeply indented coastline with numerous sheltered bays and minimal tourist development. The two main ports are Merichas (southwest) and Loutra (northeast); Loutra's harbour provides excellent protection from the Meltemi and has natural hot springs on the waterfront. The twin inland villages of Chora and Dryopis are worth visiting by scooter. Between them, the unusual double bay at Kolona — a narrow sandbar connecting a headland to the island — is one of the most distinctive anchorages in the Cyclades.
Kythnos to Cape Sounio
A 29-nm passage to the southeastern tip of Attica. Cape Sounio and its Temple of Poseidon — perched on the cliff edge 60 metres above the sea — has been a landmark for mariners since antiquity. The temple dates to 440 BCE and its Doric columns are visible from well offshore. Anchoring below the cape for a sunset visit is one of the great moments of any Aegean charter. The bay to the east provides reasonable shelter in settled weather.
Cape Sounio to Athens
A final 35-nm run along the Attic coast back to Athens. Depending on schedule, a stop at Vouliagmeni — with its thermal lake and beach clubs — can make for a relaxed last morning before disembarkation.
Season
The Cyclades charter season runs May through October. July and August bring the Meltemi — the strong northerly wind that is the defining feature of Aegean summer sailing. Passages are generally comfortable on this route, but Meltemi days may require itinerary flexibility. June and September offer warm weather with calmer winds and fewer crowds.
Embarkation
Athens offers multiple marina options — Flisvos Marina (upscale, well-serviced, close to the city centre) and Zea Marina in Piraeus are the most common starting points. Lavrion, on the southeast coast of Attica, is closer to Kea and increasingly used as an alternative.
Provisioning
Full provisioning is available in Athens before departure. Mykonos and Paros have well-stocked supermarkets for mid-trip resupply. Smaller islands (Kea, Kythnos, Sifnos) have basic provisions only.
This itinerary is a suggestion.
Your captain will adapt the route based on weather, wind conditions, and your preferences. Alternative stops may include Tinos, Andros, or Serifos depending on conditions and interests.
| Day | From | To | NM | |
|---|---|---|---|---|
| 1 | Athens | → | Kea | 49 |
| 2 | Kea | → | Syros | 48 |
| 3 | Syros | → | Mykonos | 20 |
| 4 | Mykonos | → | Paros | 32 |
| 5 | Paros | → | Sifnos | 36 |
| 6 | Sifnos | → | Kythnos | 37 |
| 7 | Kythnos | → | Cape Sounio | 29 |
| 8 | Cape Sounio | → | Athens | 35 |
| Total | 286 | |||
