This is for guests happy to skip Mykonos and Santorini, and the hype that comes with them: guests who have already done both, or would rather see them separately on a land trip. What is left is a week through the western Cyclades islands that still feel genuinely Greek from the yacht, not built for cruise-ship day-trippers. Elegant small harbours, dramatic Choras, and clear-water swim stops, without a single headline name on the route.
Starting and ending in Lavrion, about 30 minutes from Athens airport, the route covers Kea, Antiparos, Folegandros, Kimolos, Sifnos, Serifos and Kythnos, about 197 nautical miles with one genuinely long crossing (Kea to Antiparos, about 56nm) and short, easy legs the rest of the week. It suits guests who care as much about a good anchorage, lunch on board, and a beautiful evening ashore as they do about ticking off famous names.
We asked hundreds of captains at yacht shows across the Med which Cyclades islands they would pick for themselves. Folegandros, Milos and Polyaigos came out on top every time, and all three are built into this route.
The week runs Saturday to Saturday: board Saturday afternoon at Lavrion, hand back the following Saturday morning, seven nights aboard. Mid-summer meltemi is strongest in this stretch of the Cyclades, so your captain may reorder days; the shape below assumes normal conditions.
The route at a glance
- Day 1: Board in Lavrion, sail to Kea (about 15nm)
- Day 2: Kea to Antiparos (about 56nm)
- Day 3: Antiparos to Folegandros (about 26nm)
- Day 4: Folegandros to Kimolos, or Milos (about 24nm)
- Day 5: On to Sifnos (about 14 to 24nm)
- Day 6: Sifnos to Serifos (about 14nm)
- Day 7: Serifos to Kythnos (about 16nm)
- Day 8: Kythnos to Lavrion, return (about 27nm)
Our take
The true luxury and real exclusivity of a private yacht charter is going where the cruise ships can’t go.
Klara Braga Jakobsen
Yacht Reviewer & Content Lead
Day 1 – Board in Lavrion, Sail to Kea (about 15nm)
Midday: boarding at Lavrion
Lavrion sits about 30 minutes from Athens airport, so most guests are aboard within the hour of landing, no Athens traffic, no long transfer. The crew goes through the preference sheet, and you are underway with the afternoon still ahead.
Afternoon: a soft first crossing to Kea
The short run to Kea gets you out of Lavrion quickly while leaving real time for a relaxed first swim. Kea feels greener and softer than the more arid islands later in the week, and from the yacht you can choose polished harbour life in Vourkari or a quieter bay for the first water-toy session of the trip.
Broker insight
Starting from Lavrion instead of Athens shaves the first long leg and drops you straight into the quieter western Cyclades. Our pick for guests who want calm over nightlife.
Yanna Pristas
Senior Charter Broker, Active CYBA Member
Evening: Ioulida and the Lion of Kea
Ashore, head up to Ioulida for a more cultured first evening: whitewashed lanes, the remains of the medieval town, and the Lion of Kea, carved into bedrock above the village and thought to date to around 600 BC. Dinner works well either by the water in Vourkari or up in the Chora with sunset views.
Overnight: Vourkari, Kea.
Don’t Miss
- A sunset walk through Ioulida to the Lion of Kea
- Cocktails or dinner around Vourkari’s polished waterfront
- A first swim and water-toy session soon after boarding
Day 2 – Kea to Antiparos (about 56nm)
Morning: the week’s longest crossing
The longest leg of the week, and the day that makes the route feel properly Cycladic, so it is best treated as a cruising day rather than overpacked with plans. On a motor yacht the run is straightforward; on a catamaran it is much more dependent on conditions and timing, so your captain will watch the forecast closely.
Lunch: clear water at Despotiko
The reward is Antiparos, which still feels calmer and more discreet than neighbouring Paros. Lunch at anchor off Despotiko, with beach time at Agios Georgios and easy tender outings turning the back half of the long passage into a proper swim-and-toy stop.
Afternoon: Antiparos Chora
Ashore, Antiparos Chora is charming and easy: boutique shopping, low-key cocktail bars, and white lanes centred on the old Venetian castle.
Evening: the Cave of Antiparos
If the group wants a little culture between swims, the Cave of Antiparos and the ancient sanctuary site on Despotiko give the stop more substance than a simple beach day, before dinner back in the Chora.
Overnight: Antiparos.
Don’t Miss
- An evening stroll through Antiparos Chora around the 15th-century castle
- A swim and water-toy session off Despotiko’s sandy bays
- The Cave of Antiparos, if the group wants an inland detour
Day 3 – Antiparos to Folegandros (about 26nm)
Morning: a dramatic arrival
Folegandros is one of the chicest stops on this route, in a quieter and more understated way than Mykonos or Santorini. The approach itself is part of the appeal: a dramatic island profile from the sea and a handsome little harbour at Karavostasis, the practical overnight base and the island’s refuelling point.
Lunch: Katergo beach
Before heading up to the Chora, there is time for lunch at anchor off Katergo, reachable only by boat or a steep hike, clear turquoise water with no sunbeds or beach bars to interrupt it.
Afternoon: up to the Chora
The obvious move is up to Chora, where whitewashed lanes, small squares, and smart but relaxed restaurants make this one of the best dinner stops of the week. For guests who like a historical layer, the medieval Kastro and the cave of Chrysospilia add real interest, though most charters remember Folegandros for its atmosphere rather than any single sight.
Evening: sunset at Panagia
The walk up to Panagia above town is worth it for sunset alone, few views in the western Cyclades feel this complete from the yacht side of the trip. Dinner in town runs to local cheeses and matsata-style pasta, one of the route’s best evening views included.
Overnight: Karavostasis, Folegandros.
Don’t Miss
- Katergo beach, reached by boat or a steep hike
- Sunset at Panagia above the Chora
- Dinner in town with local cheeses and matsata pasta
Day 4 – Folegandros to Kimolos, or Milos (about 24nm)
Morning: under the radar
Kimolos is the sort of island repeat Greece clients love because it feels genuinely under the radar. The port of Psathi is small and simple, and that is the charm: slower village life, luminous water, and boat-only scenery close by.
Lunch: Polyaigos
The real advantage here is proximity to Polyaigos, the largest uninhabited island in the Aegean and one of the best swim-and-toy playgrounds in the Cyclades. The water runs an unreal shade of blue, tender runs into coves, paddleboards along the rock face, and a long lunch on board in total privacy.
Afternoon: the Skiadi stone
Back on Kimolos, the Skiadi stone, a giant mushroom-shaped rock formation carved by wind and erosion, is a short detour worth making before deciding on the evening.
Evening: Kimolos, or a short hop on to Milos
Chorio is worth the trip up for a more authentic Cycladic evening, white lanes and local life, the quieter of the two choices tonight. If the group does not mind a busier evening, it is a short 12nm hop further to Milos, the Island of Colours, its volcanic rock shifting shade with the light and its Chora, Plaka, one of the prettiest in the Cyclades. The statue now known as the Venus de Milo was found here before it went to the Louvre. Tell us which mood your group wants and the evening is planned around it.
Overnight: Chorio, Kimolos, or Adamas, Milos, your call.
Don’t Miss
- A slow cruise and swim session around Polyaigos
- Chorio’s white lanes, or Milos’ Plaka, whichever mood you pick
- The Skiadi stone’s wind-carved mushroom shape
Day 5 – On to Sifnos (about 14 to 24nm)
Morning: a reset day
A shorter crossing to Sifnos, where the itinerary turns gastronomic, run from wherever the group overnighted, Kimolos or Milos. From the yacht, Sifnos offers a pleasing mix of sheltered bays and elegant hilltop settlements, a genuine reset day after the longer legs earlier in the week.
Lunch: at anchor
Lunch at anchor in one of Sifnos’ sheltered bays before heading ashore, shorter mileage today leaves more of the afternoon for the island itself.
Afternoon: Kastro
Kastro is the classic visual highlight, perched above the sea with one of the most iconic little church views in the Cyclades, while Apollonia and Artemonas are where the evening takes on more social energy.
Evening: Sifnos earns its food reputation
Sifnos has a real culinary pedigree: Nikolaos Tselementes, the Sifnian chef whose 1930s cookbook was so widely used that ‘Tselementes’ became the Greek word for ‘cookbook’ itself, was born here, and the island still takes food seriously. Dinner in Apollonia or Artemonas is one of the best nights ashore on the whole route, chickpea stew slow-baked overnight in a clay pot is the dish to order.
Overnight: Kamares, Sifnos.
Don’t Miss
- Kastro and the Church of the Seven Martyrs view
- Dinner in Apollonia or Artemonas, where Sifnos earns its food reputation
- Sifnos’ slow-baked chickpea stew, a genuine island specialty
Day 6 – Sifnos to Serifos (about 14nm)
Morning: wilder and less curated
Serifos feels wilder than Sifnos and less curated, which is exactly why it works so well mid-week. The coastline is full of coves and sandy beaches that still feel unforced from the yacht, the island’s raw granite landscape giving the whole stop a tougher, more dramatic character.
Lunch: Mega Livadi and Koutalas
Mega Livadi, Koutalas, and the quieter bays around the island suit long lunches on board, tender trips to shore, and easy toy time in clear water.
Afternoon: the old mining works
Serifos carries more history than most guests expect. The old iron-mine workings and loading structures around Mega Livadi are still visible from the water, and this is where the 1916 miners’ strike over pay and working conditions ended in gunfire and won Greece its first eight-hour workday. A memorial to the strikers still stands.
Evening: sunset in Chora
Ashore, the real payoff is Chora, rising steeply above Livadi and delivering one of the best elevated evening views in the Cyclades. Sunset drinks here, looking down over the bay, close out an island with more character and less gloss than its softer neighbours.
Overnight: Livadi, Serifos.
Don’t Miss
- Sunset drinks in Chora, looking down over Livadi
- The old mining works at Mega Livadi, site of the 1916 miners’ strike that won Greece the eight-hour day
- A long swim stop at Koutalas or one of Serifos’ quieter bays
Day 7 – Serifos to Kythnos (about 16nm)
Morning: softening toward the end
Kythnos is an excellent penultimate stop, close enough to the mainland to feel practical, but still giving you some of the prettiest swim water of the week.
Lunch: Kolona
Kythnos is all about the sea day here: the island’s famous double-sided sandbar at Kolona is made for paddleboards, sea scooters, swimming, and tender runs between its two beaches, a natural spot for a final full-group lunch at anchor.
Afternoon: Loutra
Loutra adds a different mood, thermal-spring history and a laid-back harbour feel that runs different from the rest of the week.
Evening: a comfortable final night
Ashore, Chora and Driopida are pretty traditional villages, low-key and pleasant rather than showy, exactly the tone for a last night before the short run back to Lavrion.
Overnight: Merichas or Loutra, Kythnos.
Don’t Miss
- A long swim stop at Kolona, one of the most iconic anchorages nearby
- Loutra’s thermal-spring heritage and relaxed harbour feel
- A quiet final evening in Chora or Driopida
Day 8 – Kythnos to Lavrion, Return (about 27nm)
Morning: the run back
A straightforward run back to Lavrion, though there is no need to treat it as a pure delivery leg. Many charters build in one final swim stop before disembarkation, weather and timing allowing.
Lunch: one last swim
If conditions allow, Cape Sounion is the most dramatic finish, the Temple of Poseidon rising above the sea on Attica’s southern tip, and arriving back beneath that headland gives the week a properly Greek final scene. Makronissos is the quieter alternative, more austere and better for one last private swim away from traffic.
Afternoon: back to Lavrion
Either way, this last leg is about finishing gently rather than racing back: a calm bay, a last breakfast on deck, one final jump in the water before the marina.
Departure: Disembarkation is Saturday morning at Lavrion, after breakfast.
Don’t Miss
- A last swim off Cape Sounion or Makronissos
- The Temple of Poseidon rising over the sea, if conditions allow
- A calm, unhurried final morning on deck
Making This Week Work
The yacht you need
Every leg after the first is short and easy, 14 to 27nm, except the one genuinely long crossing from Kea to Antiparos at about 56nm. On a motor yacht that day is straightforward; on a sailing catamaran it needs more attention to weather and timing. Either handles the rest of the week comfortably.
How weather can change the week
The meltemi is a real factor in this stretch of the Cyclades, especially on the long Kea-to-Antiparos day. Your captain may reorder the islands around a real spell rather than fighting it; the route stays the same either way.
Best Months to Book
- Best: June or the second half of September, when the meltemi is far softer
- Toughest: mid-July to mid-August, still very charterable, just build in flexibility around the long crossing
Want Mykonos or Santorini on the route instead? See the Mykonos round trip to Santorini, or the Athens to Santorini loop. Both cover the famous islands this route deliberately skips.
