7-Day Cyclades Itinerary: Paros to Santorini

Weather month by month

Two rules before you slip lines

Level depends on the month. The route is confident-only in July-August (Meltemi 20-30 kt, built-up sea) and intermediate in June or September. Same waters, two experiences.

Keep a weather buffer. Allow two flexible days out of seven: the Meltemi can pin you down, and that is normal in the Aegean. Milos, to the west, is the strategic refuge if the wind sets in.

Day by day

Day 1, Paros (Parikia) to Naxos, 15 NM, ~3 h

Photo: Naxos · Nathan Van de Graaf / Unsplash

Sailing: ESE course, Meltemi behind if established. Cross sea possible in the Paros-Naxos channel in strong wind; wait it out above F5.

Anchorage: Naxos town quay, Med-mooring; can roll in a NW Meltemi, with a calmer anchorage in the south bay. Water and fuel at the port, supermarkets in town.

Ashore: the Portara, the monumental Apollo temple gate on Palatia islet (10 min walk, superb at sunset); the Venetian Kastro (~1 h). Sandy beaches to the south.

Warning: the quay is exposed to NW chop.

Day 2, Naxos to Iraklia (Little Cyclades), 25 NM, ~5 h

Sailing: down to the confidential archipelago between Naxos and Amorgos, Meltemi behind.

Anchorage: Agios Georgios, small harbour and bay, sandy holding. Limited facilities: one or two tavernas, a small shop, no fuel.

Ashore: 150 inhabitants, translucent water, walking trails. The contrast with Mykonos is total.

Warning: few quay spaces, arrive early.

Day 3, Iraklia to Amorgos (Katapola), 30 NM, ~6 h

Photo: Amorgos · Iason Raissis / Unsplash

Sailing: open water, Meltemi behind from the NNW, the most exposed leg.

Anchorage: Katapola, a well-protected bay on the south-west side (quay plus anchor), water at the quay, provisions in the village.

Ashore: the monastery of Chozoviotissa, clinging to a cliff 300 m above the sea (11th century, steps cut into the rock, ~1 h 30 return from the Chora; modest dress required).

Warning: the north coast of Amorgos is very exposed to the Meltemi, keep clear in strong wind.

Day 4, Amorgos to Ios, 30 NM, ~6 h

Photo: Ios · Johnny Africa / Unsplash

Sailing: westerly course; if the Meltemi is strong, break the leg via the Koufonissia.

Anchorage: Ormos Iou, a well-protected harbour with Med-mooring, or anchor off Mylopotas beach. Water, fuel, supermarkets.

Ashore: Ios, quiet by day and lively by night; the hilltop Chora (30 min on foot or shuttle); Mylopotas, one of the finest sandy beaches in the Cyclades.

Day 5, Ios to Santorini, 20 NM, ~4 h

Sailing: the arrival. Enter the caldera from the north, black and red lava cliffs rising 300 m, Oia and Fira perched on top.

Anchoring, the key technical point: the caldera is 300 to 400 m deep, so you cannot anchor inside it, the chain never reaches the bottom. Three real options:

• Vlychada marina (south coast): the only truly safe harbour, but the entrance silts up (check draught over 1.5 m), around 80 to 150 € a night, book ahead.
• Thirassia anchorage (Korfos, opposite Fira): 8 to 12 m, good holding, the best option to spend the night with the caldera view.
• Ammoudi (below Oia): a daytime tender stop only, not for overnight.

Warning: venturi effect, the Meltemi can build sharply between the caldera walls; check the forecast before entering.

Day 6, Santorini, a day ashore

Oia at daybreak before the coaches, Fira and its volcano museums, lunch at Ammoudi (by tender or down 300 steps from Oia). Optional trip to the Nea Kameni volcano and its hot springs. Sunset from the cockpit, the reason you came.

Day 7, Santorini to Paros, 40 NM, ~8 h

Sailing: the hard leg, a beat back north against the Meltemi. The golden rule: cast off before 7am to use the morning calm. If the wind is already up, wait a day or route east, in the lee of the islands, tacking your way back. Top up the fuel.

Summary table

Practical checklist

• Licence: coastal licence plus ICC plus VHF Short Range Certificate. See Do you need a licence to sail in Greece.
• Papers on board: ship's registration, third-party insurance, crew list, passports or ID cards.
• TEPAI: Greek cruising tax, payable monthly by boat size.
• Provisioning: take on water and fuel at Paros, Naxos or Ios, it is scarce in the Little Cyclades.

Booking and preparation

• Compare boats available from Paros for your dates. The route described here is a Paros-to-Paros loop; from Lavrion, see the FAQ.
• Consider charter insurance (deposit waiver), recommended for this kind of sailing.
• Flights: no direct flight from Paris to Paros; fly to Athens (ATH), then take a domestic flight or a ferry to Paros. A one-way charter ending in Santorini (JTR) is sometimes possible, with a one-way fee.
• Shore activities: the Nea Kameni volcano and the Oia sunset at Santorini, archaeology at Naxos.

See also: the guide Sailing the Cyclades and the article How much does a week's sailing in Greece cost.

Nautical data: Cyclades distance tables, harbour offices of Paros, Naxos and Santorini. Weather and temperatures: HNMS, 2025 averages. Santorini mooring: caldera pilot guides (Vlychada, Thirassia, Ammoudi). Some mooring details (berths, draught at Vlychada) should be confirmed with an up-to-date pilot before departure.

A word from the crew

Logbook. Sailing into the caldera is still our finest moment under sail in Greece: the engine echoing off the cliffs, and the plain fact that you can't anchor anywhere here. We spent the night at the Thirassia anchorage, opposite a floodlit Fira, dinghy in the water for dinner across the way.

The mistake to avoid. Leaving Santorini late on Day 7. The beat home against the Meltemi catches you by 10-11 a.m., and 40 miles of pounding become a punishment. Lift the anchor before 7 a.m., or shift a day.

Our favourite, and what we skip. Favourite: Iraklia and the Little Cyclades, the silence regained right after the crowds of Naxos. What we skip: Ios in high July if you're not after the nightlife; a stop at Sikinos or a wild anchorage makes for a finer day.

Our verdict. Beauty 5/5. Anchorages 4/5. Ease 3/5. Crowds 2/5 at Santorini in peak season. Verdict: the signature Cyclades circuit; sail it in June or September, never August, with a comfortable crew.