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Route · 14 days · round-tripYacht charter route · Cyclades

Lavrion via Mykonos & Santorini.

Sail 14 days from Lavrion through Syros, Tinos, Mykonos and Santorini, then loop home via Milos and Sifnos. Central Cyclades, minimal motoring.

The route

Day-by-day route

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Kea
Day 1

Lavrion → Kea (Vourkari)

A gentle 18-mile shakedown east from Lavrion to Kea, with Vourkari's seafood quay waiting at the end of the afternoon.

Distance

15 NM

Sailing

~3h at 5 kn

At a glance

Route at a glance

Best season

May – mid-October (peak Jun – Sep, meltemi Jul – Aug)

Duration

14 days

Departure

Lavrion

Sailing area

Cyclades

Route summary

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The full story

Day-by-day journey

Named anchorages, mooring notes and things to do for every leg of the week — the map follows along as you scroll.

Day 1 / 14
Kea
1
Day 1

Lavrion → Kea (Vourkari)

Starting from Lavrion rather than Alimos hands you a head start: the boat sits a dozen miles nearer the islands before you even slip the lines. There is no rush on day one. Load provisions, sort the cabins, and push off after lunch when the base has finished the handover. The crossing runs east past Cape Sounion, taking the northerly on the quarter for a fast, forgiving reach. Vourkari opens up on Kea's northwest corner, a long quay with room to lie stern-to and reliable cover from the prevailing north. Fishing boats still work off the same jetties, and the ouzeris behind them grill whatever came in that morning. We usually settle the crew here for the first night, with the hilltop capital of Ioulida a short taxi ride up for anyone still restless after dinner. An easy start sets the tone.

Things to do

See the archaic Stone Lion above Ioulida

Snorkel the Patris wreck off Koundouros

Grilled octopus at a Vourkari ouzeri

Evening stroll through Ioulida's marble lanes

Mooring tip

Lie stern-to on Vourkari's quay with lazy lines, roughly EUR 25-35 a night, and you're well tucked from the northerly Meltemi. If the quay fills up, motor two miles east to Otzias and drop the hook on sand in 6-8 metres.

Syros
2
Day 2

Kea → Syros (Ermoupoli)

Leave early. Before about one in the afternoon the wind sits under twelve knots, and you want as many miles as possible banked before the Meltemi wakes up. Thirty-two miles of open water lie between Kea and Syros, so the second half of the passage tends to turn into a quick beam reach with a building sea. Tuck a reef in before you need it and the leg stays comfortable. Ermoupoli is the working capital of the Cyclades, its neoclassical houses stacked up the hillside in faded ochre and rose. The town quay is among the most forgiving stern-to berths in the islands, holding well in most conditions. Ashore, the marble expanse of Miaouli Square fills up after dark, and the climb to Ano Syros rewards you with the old Catholic quarter and the whole harbour laid out below.

Things to do

Climb to Ano Syros's Catholic quarter

Taste loukoumi at an old Ermoupoli confectioner

Cross Miaouli Square after dark

Swim the rock ledges at Asteria

Mooring tip

Ermoupoli's town quay is free and you set your own anchor; holding is good and shelter is unusually broad for the Cyclades. If it's packed in high season, Manna Marina just north takes you for EUR 60-80 a night.

Tinos
3
Day 3

Syros → Tinos

Short does not mean lazy. The gap between Syros and Tinos squeezes the northerly and can add five knots to whatever the forecast promised, and by late July a twenty-five-knot afternoon in the channel is routine. Ride it on the beam and the fourteen miles fly past, but aim to have lines ashore by four before the swell stacks up at the harbour mouth. Tinos wears two identities. It is the great Orthodox pilgrimage island, where the faithful climb to the church of Panagia Evangelistria, and it is the marble-carving heart of the Aegean, a craft you can still watch in the workshops of Pyrgos up north. Inland the hills are scattered with ornate Venetian dovecotes. Book nothing, but arrive early: the new harbour holds moderate sand, so lay out plenty of scope.

Things to do

Watch marble carvers at work in Pyrgos

Walk the dovecote trail above Falatados

Lunch on artichokes a la polita

Wander the boulder field at Volax

Mooring tip

Go stern-to in the new harbour for EUR 25-40 a night, but treat the sand as moderate holding and set your anchor with long scope. When the Meltemi tops 25 knots, the inner small-craft basin rides much calmer.

Mykonos
4
Day 4

Tinos → Mykonos

The hop to Mykonos is the shortest sail of the fortnight, but do not let eight miles fool you. The Tinos strait reliably blows five knots over the forecast and throws up a short, jarring chop by mid-afternoon, so it earns its respect. In July and August the sensible plan is a pre-booked slot at Tourlos, the newer marina north of town; reserve it online a day ahead and the evening looks after itself. The old town quay is free but wide open to swell, tenable only when the northerly stays under eighteen knots. There's time before dinner for a swim, so anchor off Ornos or Psarou on the way in. Then it's a short ride into the whitewashed lanes, and the caique to ancient Delos runs from the old port if anyone wants the ruins.

Things to do

Catch the caique to ancient Delos

Beach lunch at road-free Agios Sostis

Sunset along the Little Venice waterfront

Hike the Armenistis lighthouse loop

Mooring tip

Book Tourlos New Marina online 24 hours ahead for July and August; expect EUR 70-110 a night at peak. The free town quay only makes sense when the northerly is forecast below 18 knots, and even then it rolls.

Paros
5
Day 5

Mykonos → Paros (Naoussa)

This is the leg crews remember. Twenty-two miles of open Aegean run southwest with the Meltemi on the quarter, the boat surfing along at hull speed for four or five hours of pure downwind sailing. Keep an eye out as you pass the Naxos channel, which funnels the strongest gusts of the day and can catch a lazy helmsman out. Naoussa sits on the north coast of Paros, its little Cycladic fishing port ringed by tavernas that spill their tables right to the water. Boats come and go, nets dry on the quay, and the whole scene tips over into a lively dinner crowd once the sun drops. Slots are tight and tend to go by five in the afternoon. If the harbour is full or the Meltemi is pushing in, drop anchor just east in Plastira Bay on good sand.

Things to do

Snorkel the smooth granite of Kolymbithres

Taste local wine at a Marpissa vineyard

Ouzo on the Naoussa fishing quay

Walk the marble paths of Lefkes

Mooring tip

Naoussa's small harbour goes stern-to for EUR 30-50 a night and usually fills by five. If you miss out, anchor half a mile east in Plastira Bay on sand in 5-7 metres, or fall back on larger Parikia.

Ios
6
Day 6

Paros → Ios

Today the Aegean shows its teeth. The twenty-eight miles south pass through the Naxos-Sikinos channel, one of the fiercest Meltemi stretches in the central Cyclades, where a steady twenty-two to thirty knots on a port-tack reach is normal fare. Shorten sail early, before the channel rather than in it, and the passage becomes exhilarating instead of frantic. Ormos, the port of Ios, gives good shelter once you're inside, and its marina has been growing; the older quay still does the job when berths are short. Save Mylopotas, the long sandy sweep a mile south, for a daytime swim only, since it offers nothing overnight in a blow. Ios has shaken off some of its party reputation, though the Chora windmills still draw a crowd at sunset and the little squares hum late into the night.

Things to do

Hike to the reputed tomb of Homer

Swim the south-coast sands of Manganari

Sunset drinks by the Chora windmills

Find a late rembetika bar in Chora

Mooring tip

Ormos harbour takes you stern-to for EUR 25-40 a night; grab a new-marina slot in advance when one's available. Treat Mylopotas strictly as a lunch anchorage, since it becomes untenable overnight in any Meltemi.

Santorini
7
Day 7

Ios → Santorini

Santorini asks for good timing. The caldera is a drowned volcano with water hundreds of metres deep, so swinging at anchor is simply off the table, and you want a calm window and full daylight to take it all in from the water. Leave Ios at first light and the eighteen miles slip by easily on the morning breeze. Vlychada, on the south coast, is the one genuine overnight: a sheltered marina with road access and berths worth booking well ahead in high season. Tie up by lunchtime and the afternoon is yours. Most crews grab a taxi up to Oia for the sunset that everyone photographs and few forget, then work back down through the wine country. The volcanic soil here makes a bone-dry Assyrtiko you'll want to taste at the source.

Things to do

Taxi to Oia for the cliff-top sunset

Taste Assyrtiko at Santo Wines or Sigalas

Swim below the cliffs at Red Beach

Fava with capers in Megalochori

Mooring tip

Vlychada Marina is the only reliable berth, stern-to at EUR 60-100 a night, and it needs booking ahead in peak weeks. The cruise-ship buoys off Thirasia are a poor backup, so don't plan around them.

Folegandros
8
Day 8

Santorini → Folegandros

The pointy end of the trip starts here. Turning northwest to begin the loop home means putting the Meltemi on the nose for the first time, and the twenty-two miles to Folegandros are all beating and tacking rather than reaching. Pick your moment, keep the crew fed, and it's a satisfying sail rather than a slog. Karavostasi is the only working port, snug enough behind the northerly but wide open to anything from the south, so read the forecast before you commit. The real Folegandros waits high above on the cliff edge, where the Chora ranks among the loveliest in all the islands; it's a thirty-minute climb up the old kalderimi or a quick taxi. On the way in, drop the hook at Katergo, a boat-only cove with pale water, for a swim you'll have half to yourselves.

Things to do

Climb to Chora's cliff-edge Panagia church

Swim the boat-only cove at Katergo

Try matsata pasta with goat ragu

Walk the kalderimi to Ano Meria

Mooring tip

Karavostasi goes stern-to for EUR 25-40 a night with only a handful of slots; anchor on sand in 4-7 metres in the bay just east if it's full. Steer clear altogether in southerlies, as the port has no cover from the south.

Milos
9
Day 9

Folegandros → Milos (Adamas)

Another twenty miles into the wind, another pair of long tacks northwest, and the reward at the end is one of the most protected harbours in the western Cyclades. Adamas lies at the head of a deep bay that bites right into the heart of Milos, and once you clear the entrance the sea flattens and the breeze falls away to almost nothing. Shelter here is close to total, whatever the wind is doing outside. Time your run to pass Sarakiniko with a swim in mind: the wind-carved white rock looks like the surface of the moon, though the anchorage is exposed and only worth stopping at in settled air. Milos rewards a wander ashore too, from the catacombs near Plaka to the painted boat garages of Klima, where fishermen still keep their caiques.

Things to do

Swim beneath the white cliffs of Sarakiniko

Snorkel the sea caves at Papafragas

Take in the view from Plaka Castle

Photograph the syrmata boathouses at Klima

Mooring tip

Adamas town quay goes stern-to for EUR 30-50 a night with excellent all-round shelter thanks to the long bay. Pollonia in the northeast is cheaper but lies exposed when the Meltemi blows from the north.

Kamares
10
Day 10

Milos → Sifnos (Kamares)

Eighteen miles north, and the sailing eases off. Kamares Bay on the west coast is the standard overnight, well covered from north and northeast, though its mouth faces west. Come late August, when the Meltemi picks up a westerly slant, swell can roll straight in and unsettle the bay; that's the cue to shift round to Platys Gialos on the south coast instead. Whichever you choose, the real reason to stop is the food. Sifnos is where Greek islanders send you for dinner: chickpea revithada left to cook overnight in a wood oven, lamb baked slowly in clay mastelo pots, recipes that trace back to the island's own nineteenth-century cookbook tradition. Between meals, the walk out to the little monastery of Chrysopigi, marooned on its rocky spit near Faros, is worth the afternoon.

Things to do

Walk to Chrysopigi monastery near Faros

Eat mastelo lamb up in Artemonas

Visit a pottery workshop in Vathy

Swim the calm cove at Vathi

Mooring tip

Anchor on sand in 5-8 metres in Kamares Bay, or take the small quay for EUR 20-30 a night when a slot's free. Once the wind clocks into the west, move round to Platys Gialos on the south coast for a settled night.

Serifos
11
Day 11

Sifnos → Serifos (Livadi)

A gentle fourteen-mile hop on paper, but Serifos keeps you honest at the far end. Livadi Bay opens straight into the Meltemi and works like a funnel, and while the sandy bottom holds well in theory, the steady pull stretches out anchors and dragging is the classic Serifos mishap. Lay plenty of chain, dive down to check the hook is properly buried, and stay aboard for the first hour before anyone heads ashore. It pays off. Above the port, the Chora tumbles down the hillside in tiers of white, one of the most photogenic villages in the whole archipelago, reached on foot up the old donkey path or by taxi if legs are tired. The kafeneia in the little squares do a fine chickpea revithada, and the windmills above town catch the last of the light.

Things to do

Climb the donkey path up to Chora

Eat chickpea revithada in a kafeneio

Swim at south-coast Psili Ammos

Watch sunset from the Chora windmills

Mooring tip

Anchor in Livadi Bay on sand in 5-8 metres and lay out long scope, or go stern-to on the town quay for EUR 20-30 a night. Above 22 knots the drag risk climbs, so always dive the anchor before you leave the boat.

Kythnos
12
Day 12

Serifos → Kythnos (Merichas)

Fifteen miles north brings you to Kythnos, and the headline here is not the harbour but a beach you can only reach by boat. Merichas, the small ferry port on the west coast, is a fine enough fallback for a quiet night on the quay. The prize lies six miles further up the coast at Kolona, a slender two-hundred-metre ribbon of sand that ties the islet of Agios Loukas to Kythnos proper, with clear shallow water lapping both flanks of the spit. Anchor off, and the swimming becomes the whole point of the day; there's no village to walk to, no schedule to keep. We tend to drop the hook by mid-afternoon and stay put right through dinner, watching the light change over the sandbar. It's the kind of anchorage crews talk about for years.

Things to do

Anchor and swim off the Kolona sandbar

Soak in the hot springs at Loutra

Cycle the ridge road to Driopida

Sfougato cheese pie in a Driopida taverna

Mooring tip

Anchor for free on sand in 4-6 metres at Kolona, where the islet screens you from the northerly Meltemi. Merichas town quay runs EUR 20-30 a night, and Loutra has a few marina berths beside its natural hot springs.

Lavrion
13
Day 13

Kythnos → Lavrion

The run home is one of the gentler final legs in the Cyclades, and that's the quiet advantage of a Lavrion base: sitting east of Athens, it saves you the longer haul that an Alimos charter faces. Twenty-four miles northwest, with Cape Sounion rising off to starboard about halfway across, the columns of Poseidon's temple marking the last real landmark before the marina. In a fading evening Meltemi the leg can turn into a lazy downwind drift, sails goose-winged, no one in a hurry to arrive. Stop the boat under the temple for a farewell swim if the timing works. Top up at the fuel berth on the way in so the tanks are full for handover, then find the crew a table at a harbourside taverna. Bases here usually want the boat alongside by five the evening before.

Things to do

Swim below the temple at Cape Sounion

Refuel and rinse down at Lavrion

Crew dinner at a Lavrion harbour taverna

Browse the shops in Lavrion town

Mooring tip

Lavrion's Olympic Marina takes you stern-to with lazy lines for EUR 60-90 a night. Refuel at the fuel berth by the entrance before you moor, and confirm your handover slot with the base 24 hours ahead.

Lavrion
14
Day 14

Lavrion → Check-out

The last morning is straightforward. The base likes the boat handed back before nine, and the check-out goes quickest with the skipper aboard while the manager walks through the inspection. Assuming nothing is flagged, the security deposit comes back within about a week. One of the quieter perks of a Lavrion finish is the run to the airport: roughly fifty minutes by road, against the longer, more traffic-bound crawl from the marinas closer to Athens. There's usually time for one last frappe and a bite at a harbour kafeneio before the goodbyes, and the coffee here costs a fraction of what you'd pay down in Glyfada. Settle up, photograph anything that needs noting before you sign, and thank the dock crew who've looked after the lines all fortnight. Then it's transfers, and already talking about next year.

Things to do

Final walk-through with the base manager

Last frappe at a Lavrion kafeneio

Airport transfer, 50 minutes from Lavrion

Tip the dock crew for good service

Mooring tip

Hand the boat back before nine and expect the deposit within a week of a clean inspection. Photograph any existing marks and get them noted in writing before you sign the check-out sheet.

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