Cyclades Itinerary for Luxury Yacht Charters from Athens
The Cyclades are the islands most people picture when they think of Greece, and they are an easy reach from Athens. Lavrio, where many of the yachts in this area are based, is about 40 minutes by car from Athens airport, so you can land in the morning and be swimming off Kea by mid-afternoon.
This 7-night loop keeps most legs to two or three hours and mixes the two islands everyone has heard of, Mykonos and Paros, with four quieter ones: Kea, Antiparos, Sifnos and Kythnos. Those are the stops guests tend to remember. In July and August the meltemi blows from the north, sometimes at force 6 to 7 for several days, so your captain may reverse the loop or swap an island to keep you in sheltered water. Treat the plan below as a starting point, not a timetable.
CYCLADES LOOP FROM ATHENS
Lavrio → Kea → Syros → Mykonos → Delos → Paros → Antiparos → Sifnos → Kythnos → Lavrio
7 Nights | 10‑knot cruising speed | May to October
Theme: Two headline islands, four quiet ones, and short days on the water.
DAY 1 — LAVRIO → KEA (Otzias Bay)
Distance: 15 NM
Duration: ~1 hr 30 min
Morning Routine
Board in Lavrio from late morning. The crew show you round while your bags are unpacked, and lunch is served once you are clear of the harbour.
Afternoon Routine
Kea is the closest Cycladic island to Athens and most visitors sail straight past it, which is the point. Anchor in Otzias Bay, a sandy, sheltered bay on the north coast, for the first swim of the week. If you want to stretch your legs, it is a short drive up to Ioulida, the hill town, and the Lion of Kea, carved straight into the rock in the 6th century BC.
Evening Routine
Dinner on board, or take the tender round to Vourkari, a small harbour lined with fish tavernas that fills up with Athenian yacht owners at weekends.
DAY 2 — KEA → SYROS (Ermoupoli)
Distance: 31 NM
Duration: ~3 hrs 10 min
Morning Routine
An early swim and breakfast, then the longest leg of the first half of the week, done in the morning while the wind is lightest. Syros comes into view around lunchtime.
Afternoon Routine
Ermoupoli is the capital of the Cyclades and looks nothing like the whitewashed villages elsewhere: 19th-century merchants’ houses, the marble-paved Miaoulis Square and the Apollo Theatre, modelled on La Scala. It is a working town rather than a resort, which is exactly why it is worth a stop.
Evening Routine
Walk up to Ano Syros, the medieval Catholic quarter on the hill above the port, for sunset, then dinner in town. Before you leave, buy a box of loukoumi from one of the old confectioners on the harbour; Syros has been making it for almost two hundred years.
DAY 3 — SYROS → MYKONOS (Ornos Bay)
Distance: 20 NM
Duration: ~2 hrs
Morning Routine
A slow start, then two hours east. The old port in Mykonos town is crowded and short of space for larger yachts, so the captain will usually anchor in Ornos Bay or off Psarou on the south coast.
Afternoon Routine
Lunch ashore at Nammos on Psarou beach if you want to see Mykonos at full volume, or stay on board with the water toys while the beach clubs warm up. Scorpios at Paraga, a short tender ride along the coast, is the place for the sunset crowd.
Evening Routine
Tender into town for Little Venice and the windmills above it, then dinner in the lanes behind the harbour. Mykonos runs late; the tender will be waiting whenever you are ready.
DAY 4 — MYKONOS → DELOS → PAROS (Naoussa)
Distance: 20 NM total
Duration: ~2 hrs
Morning Routine
Delos is about twenty minutes from Ornos. The whole island is an archaeological site: the birthplace of Apollo in Greek myth, and for centuries one of the busiest ports in the Aegean. Go first thing, before the excursion boats arrive from Mykonos and the heat builds, and allow two to three hours for the Terrace of the Lions and the merchants’ houses with their floor mosaics.
Afternoon Routine
Lunch on board on the way south to Paros. Naoussa, on the north coast, is a fishing harbour guarded by the ruins of a small Venetian fort, and it has some of the best food in the Cyclades.
Evening Routine
Larger yachts anchor in Naoussa Bay and tender in. Ouzo and grilled octopus on the harbour, then dinner in the old town behind it.
DAY 5 — PAROS → ANTIPAROS (Despotiko)
Distance: 19 NM
Duration: ~1 hr 55 min
Morning Routine
The channel between Paros and Antiparos is shallow, so most yachts go round the outside of Antiparos rather than through it. Breakfast on the way.
Afternoon Routine
Anchor between Antiparos and the uninhabited island of Despotiko. The water here is shallow and sandy and about as clear as the Aegean gets. On Despotiko, archaeologists have been uncovering a sanctuary of Apollo for more than twenty years, and you can walk up to the dig from the beach.
Evening Routine
Stay at anchor for a quiet night, or tender over to Antiparos town, essentially one main street of small bars and restaurants. It is lively in August and pleasantly sleepy the rest of the season.
DAY 6 — ANTIPAROS → SIFNOS (Vathi)
Distance: 17 NM
Duration: ~1 hr 45 min
Morning Routine
A short morning run west to Sifnos and into Vathi, a deep, almost enclosed bay on the south-west coast with a beach and a few tavernas.
Afternoon Routine
Sifnos is the food island of the Cyclades. Nikolaos Tselementes, whose family came from Sifnos, wrote the cookbook found in most Greek kitchens, and the local dishes, revithada (chickpeas baked overnight in a clay pot) and mastelo (lamb slow-cooked in red wine), are still made in pots from the island’s own potteries. Take a car for the afternoon: the monastery of Chrysopigi on its rock at the water’s edge, and Kastro, the old capital, with the little church of the Seven Martyrs on the rocks below it.
Evening Routine
Dinner in Apollonia or Artemonas, the two villages in the middle of the island, then back to a calm night in Vathi.
DAY 7 — SIFNOS → KYTHNOS (Kolona)
Distance: 34 NM
Duration: ~3 hrs 25 min
Morning Routine
The second long leg, north past Serifos. If the meltemi is blowing this will be the bumpiest morning of the week, and the captain may leave earlier or break the trip with a lunch stop on Serifos.
Afternoon Routine
Kolona is a sandbar on the west coast of Kythnos that joins the island to the islet of Agios Loukas, with sea on both sides. It is one of the most photographed anchorages in Greece and, outside August, rarely crowded.
Evening Routine
Last night on board. If you want one more outing, the hot springs at Loutra are a short drive away; otherwise it is dinner on deck and a late swim off the stern.
DAY 8 — KYTHNOS → LAVRIO (Disembarkation)
Distance: 24 NM
Duration: ~2 hrs 25 min
Morning Routine
Breakfast underway and back in Lavrio by late morning. From the quay it is 40 minutes to Athens airport.
Good to Know
Best months: June and September. The sea is warm, everything is open and the meltemi is usually lighter than in July and August.
The meltemi: a northerly summer wind that can blow for days at a time. Sailing yachts handle it well; on a motor yacht the captain may change the order of the islands. They make the call on the day.
Why Lavrio: it is closer to the Cyclades and to the airport than the Athens marinas, which saves two to three hours of cruising at each end of the week.
APA: as with most charters in Greece, food, drink, fuel and port fees are paid from an Advance Provisioning Allowance on top of the charter fee, usually around 30 per cent.
The most suitable yachts for this itinerary are based in Lavrio and Athens, so there is no delivery fee to reach the start:
GRANDE AMORE - 144ft Motor Yacht
WIND OF CHANGE - 95ft Sailing Yacht
MOONLIGHT - 59ft Sailing Catamaran
To book your luxury yacht charter in the Cyclades please contact your broker at charter@supersailyachts.com
Photography via Unsplash: Dimitris Kiriakakis, Despina Galani, Johnny Africa, Jesse Paul, Yannis Papanastasopoulos.