A Cyclades Sailing Route: Mykonos, Paros, Naxos & the Small Cyclades

The Cyclades are the Greece of the postcards — whitewashed villages, blue domes, and the kind of clear, wind-driven water that makes real sailors happy. This is a ground for confident crews: the meltemi gives the islands their reputation, and the reward is a week of genuine sailing between islands that each feel distinct. Here is a route that balances the iconic with the quiet.

Day 1 — Board at Mykonos or Paros

Fly into Mykonos or Athens and board mid-archipelago. A first evening at anchor off Mykonos, with Little Venice glowing at sunset, sets the tone.

Day 2 — Delos and Rinia

Sail the short hop to Delos — an entire archaeological city, uninhabited since antiquity. Day visits ashore only; anchor overnight in the empty bays of neighbouring Rinia.

Day 3 — Naoussa, Paros

A working fishing harbour turned elegant without losing itself: octopus drying on the quay, cocktails in the old port. Naoussa is one of the best all-round overnights in the Cyclades.

Day 4 — Naxos

The greenest, most self-sufficient Cyclade — marble villages inland, long beaches to anchor off, and the Portara gate framing the sunset. Provisioning here is a pleasure.

Day 5 — Koufonisia and the Small Cyclades

South to the Small Cyclades: Koufonisia's turquoise pools and swim-through sea caves at Pori are the highlight. This is the quiet, luminous heart of the group — come before the day-trippers.

Day 6 — Ios or Polyaigos

Depending on wind and crew, either lively Ios or the uninhabited Polyaigos, which has the clearest water in the whole archipelago. Pure anchorage sailing.

Day 7 — Toward Santorini (or back)

Some crews end at Santorini, sailing into the flooded volcano for the most dramatic anchorage in Greece before flying home from Thira. Others loop back to the departure base for a final swim.

Practical notes

• The meltemi. This strong north wind blows mainly mid-July to early September and is at its most powerful here — exhilarating for experienced crews, demanding for beginners. See when the meltemi blows.
• First time or with kids? Consider the calmer Ionian or Saronic instead — compare Greece's grounds.
• Ready to plan? Browse Cyclades charters or ask our concierge.