7-Day Cyclades Sailing Itinerary: A Realistic Week by Yacht
This itinerary is a round trip from Vlychada Marina on Santorini, using short legs of 15–28 nautical miles and moving from the most exposed crossing on day one to sheltered anchorages later in the week. Total distance is roughly 175 nautical miles over seven nights. It works in June and September; in July and August, treat every day as a plan A with a plan B. It is one of the classic routes for a yacht charter in Greece.
Starting from Paros or Mykonos instead? The same loop works from either island: join it at Paros or Naxos and sail it in the same order. For a Mykonos start, our Mykonos yacht charter guide sets out the nearby routes.
The route
Day 1: Santorini to Folegandros (about 22 NM). Board at Vlychada (see our Santorini yacht charter guide), cast off in the afternoon. This is the roughest crossing of the week. Arrive at Chora, the clifftop village, in the evening.
Day 2: Folegandros to Milos via Kimolos (about 25 NM). Stop at Kimolos for lunch at anchor, then on to Milos: Sarakiniko’s white rock, Kleftiko sea caves and the Klima boathouses.
Day 3: Milos to Sifnos (about 15 NM). A short hop to the island known for its food. Overnight at Kamares.
Day 4: Sifnos to Paros via Antiparos (about 20 NM). Swim at the Antiparos coves, then on to Naoussa on Paros and its Venetian harbour.
Day 5: Paros to Naxos (about 18 NM). Lunch on the west coast beaches, then explore the Portara gate and the old town.
Day 6: Naxos to Koufonisia and Schinoussa (about 28 NM). The Small Cyclades are made for yachts: sea caves, rock pools and turquoise water.
Day 7: Koufonisia/Schinoussa to Ios (about 26 NM). Ios has a proper harbour, Chora’s maze of steps and churches, and beaches at Mylopotas and Manganari.
Day 8: Ios to Santorini (about 22 NM). A calmer return crossing. Aim to disembark by midday.
Wind: how to adapt the route
The meltemi decides this week (see the best time to sail in Greece). Long legs, especially the Folegandros crossing on day one, are best done in the morning calm. In strong wind, reorder stops rather than fight it: the itinerary is designed to move from exposed to sheltered water, so you can shorten the exposed legs but should not skip the sheltered days. A monohull handles the day-one crossing better than most catamarans; a fast motor yacht makes it easy.
Practical notes
Vlychada is small, so provisioning is slower in peak season and some boarding may be by dinghy: confirm logistics with your operator. Plan an extra night ashore before a long-haul flight home.
If you would rather avoid the exposed first crossing, start in Paros and run the second half of the route first, or choose the Saronic or Ionian instead.
Frequently asked questions
Can you sail a 7-night Cyclades itinerary on a catamaran?
Yes, but book early and, in high season, plan to reach harbours by mid-afternoon to find space. See our catamaran vs monohull guide.
Is a Cyclades sailing itinerary suitable for beginners?
It is better suited to crews with some experience or a hired skipper. For a first week, the Ionian and the Saronic Gulf are easier.
How much does a 7-night Cyclades yacht charter cost?
The charter fee follows the prices in our Greece cost guide. Add fuel, mooring fees, provisioning and end cleaning, and check whether VAT is included in the quote.
What if the meltemi blows for several days in the Cyclades?
Shorten your legs, stay in sheltered ports, and use the Small Cyclades and Sifnos as fallback stops until the wind eases.
