athens-mykonos-santorini-paros
Route · 14 days · round-tripYacht charter route · Cyclades

Athens via Mykonos & Santorini.

Sail a 14-day Cyclades loop from Athens through Mykonos, Paros and Santorini, back via Milos and Sifnos. Anchorages, mooring and wind, day by day.

The route

Day-by-day route

Click any pin on the map or any day in the route summary below to see that day's stop, story and photos.

Kea
Day 1

Athens (Alimos) → Kea (Vourkari)

A gentle 20-mile shake-down out of Alimos, rounding Cape Sounion before the easy hop across to Kea's sheltered Vourkari bay.

Distance

35 NM

Sailing

~7h 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

Athens

Sailing area

Cyclades

Route summary

Click any day to jump back to the map and see its photos, narrative and mooring tip.

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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

Athens (Alimos) → Kea (Vourkari)

Provisioning always runs long on the first morning, so we rarely clear Alimos before eleven. Once the trolleys are unloaded and the fridge is stocked, point the bow east-southeast and settle in. Within the hour the columns of Poseidon's temple stand up on the headland at Sounion, off to starboard, and they make a tidy mark for the channel out into open water. The rest is a twenty-mile reach across to Kea, riding whatever northerly the day has built. Vourkari sits on the island's northwest shoulder and does the job of a first night well: good cover from the prevailing Meltemi, a generous stern-to quay, and a run of little seafood ouzeris where the grilled octopus comes straight off the coals. Korissia, the ferry town next door, is the cheaper fallback when the wind stays soft.

Things to do

Climb to Ioulida's marble backstreets at dusk

Find the 6th-century BC Lion of Kea

Snorkel the Patris wreck off Koundouros

Grilled octopus at a Vourkari ouzeri

Mooring tip

Stern-to in Vourkari on lazy lines, roughly €25-35 a night for a 45-footer, with solid cover from the northerly. When the quay fills, drop the hook two miles east in Otzias, sand at 6-8 m.

Syros
2
Day 2

Kea → Syros (Ermoupoli)

Leave Vourkari not long after coffee. The morning air is usually still under twelve knots, and the Meltemi tends to hold off until the early afternoon, which gives you a soft start on the thirty-two-mile run down to Syros. When the wind does fill, the back half of the leg turns into a fast beam reach with a building sea, so tuck a reef in before you need it rather than after. Ermoupoli waits at the head of a deep, well-shaped harbour, its neoclassical old town stacked up the hillside in ochre and white. The town quay here is about as forgiving as stern-to mooring gets in these islands: sheltered whatever the wind is doing, plenty of room, and the capital's cafés a two-minute walk off the passerelle.

Things to do

Wander Ano Syros and its Catholic quarter

Taste loukoumi at a 19th-century sweet shop

Evening stroll across Miaouli marble square

Swim the rock ledges at Asteria

Mooring tip

Stern-to on Ermoupoli's town quay is free, but bring your own anchor as lazy lines are hit-and-miss. Shelter is excellent from any direction. For a serviced berth, Manna marina charges around €60-80 a night.

Tinos
3
Day 3

Syros → Tinos

The gap between Syros and Tinos is one of the windiest stretches in the group. The geography funnels the Meltemi, so a benign twenty-knot forecast can show twenty-five on the water by mid-afternoon, and late-July gusts run higher still. Take it on the beam and enjoy the pace, but have the boat tied up well before four, before the swell starts stacking at the harbour mouth. Tinos town has stern-to berths in the newer basin, though the holding is only fair; the smaller inner harbour, kept for charter and local boats, is the calmer bet when it blows hard. Ashore, the island is the marble-carving heart of the Aegean and the great Orthodox pilgrimage site, the church of Panagia Evangelistria drawing the faithful up its long marble-paved approach.

Things to do

Watch marble carvers at work in Pyrgos

Walk the dovecote trail above Falatados

Artichoke à la polita in a courtyard taverna

Sunset among the boulders at Volax

Mooring tip

Stern-to in the new harbour runs about €25-40; the bottom is moderate sand, so lay a long scope and set hard. If more than 25 knots of Meltemi is forecast, take the calmer inner small-craft harbour instead.

Mykonos
4
Day 4

Tinos → Mykonos

A short leg, this one, barely eight miles across to Mykonos. Do not let the distance fool you: the straight-line course cuts through open channel where the wind sits a good five knots above the regional number, and the afternoon sea gets short and awkward. In July and August you really want a slot booked at Tourlos, the new marina north of town, twenty-four hours ahead online. The old town quay is free but wide open to swell and only worth it when the Meltemi is under eighteen knots. There is no rush to arrive, so break the passage with a swim at Ornos or Psarou before you moor. Mykonos earns its reputation after dark, but the quieter daytime pleasure is the boat across to Delos and its ruined marble avenues.

Things to do

Boat across to the ruins of Delos

Beach lunch at road-less Agios Sostis

Little Venice waterfront at sunset

Hike the Armenistis lighthouse loop

Mooring tip

Book a stern-to slot at Tourlos New Marina online for peak season; expect €70-110 a night. The free town quay is only safe below about eighteen knots of northerly, as swell builds quickly across the entrance.

Paros
5
Day 5

Mykonos → Paros (Naoussa)

This is the leg crews remember. Twenty-two miles southwest to Paros, the Meltemi settled on the quarter, and the boat surfing along on a broad reach for four or five hours of proper open-water sailing. Keep an eye out as you pass the Naxos channel, where gusts come down off the high ground harder than you expect. Naoussa waits on the north coast, an old Cycladic fishing port that has grown into a smart little harbour village without losing the boats that gave it its name; the octopus still hangs drying on lines by the water. If the northerly is pushing into the inner basin, there is easy anchoring in the bay just outside. Save the evening for a glass of ouzo at the fishermen's quay as the light goes.

Things to do

Snorkel the sculpted rocks at Kolymbithres

Wine tasting at a Marpissa vineyard

Ouzo on the Naoussa fishing quay

Walk Lefkes' marble lanes at dusk

Mooring tip

Naoussa's harbour is small and stern-to, €30-50 a night, and often full by five in the afternoon, so arrive early. If it's taken, anchor half a mile east in Plastira Bay, sand at 5-7 m and sheltered from the north.

Ios
6
Day 6

Paros → Ios

The Naxos-Sikinos channel is where the Meltemi shows its teeth. Unlike the downwind runs behind you, this twenty-eight-mile leg puts the wind forward of the beam, and through the channel itself you can expect a steady twenty-two to thirty knots on a hard port-tack reach. Reef down before you leave the lee of Paros and aim to have the anchor down inside Ormos well before four. The harbour there is sheltered and the marina is being enlarged; the old quay still works, though slots are few. A mile south, Mylopotas is the swimming bay of choice for the afternoon, a long sweep of sand that empties out once the day boats leave. Ios has a reputation as a party island, but the walk up to the windmills above Chora at sunset is a calmer pleasure.

Things to do

Hike to the reputed tomb of Homer

Swim the sands at Manganari Bay

Sunset drinks by the Chora windmills

Late rembetika in a Chora square

Mooring tip

Stern-to in Ormos harbour, €25-40 a night, with pre-bookable slots in the new marina when open. Mylopotas is a daytime anchorage only, sand at 5-8 m; it becomes untenable overnight once the Meltemi sets in.

Santorini
7
Day 7

Ios → Santorini

The mileage is nothing, but this leg wants a calm window and good daylight, because arriving at Santorini is no place to be rushed. The honest advice is to forget anchoring in the caldera. The water inside drops past two hundred metres a short way off the cliffs, so swinging on your own hook is simply not on; the only holding is off Thirasia at the cruise-ship buoys, and that is unreliable at best. Instead, aim for Vlychada on the south coast, a proper sheltered marina with road access for a crew change. Leave Ios at first light, be tied up by lunchtime, and put the afternoon into a taxi up to Oia. The sunset there is a cliché for a reason, but go early and claim a spot before the coach crowds arrive.

Things to do

Taxi up to Oia for the sunset

Wine tasting at Santo Wines or Sigalas

Swim below the cliffs at Red Beach

Fava with capers in Megalochori

Mooring tip

Vlychada Marina is stern-to at roughly €60-100 a night and needs booking ahead in peak season. Treat the Thirasia cruise buoys as a last resort only; the caldera's depth rules out free anchoring almost everywhere.

Folegandros
8
Day 8

Santorini → Folegandros

From here the trip turns for home, and home means working back up against the Meltemi in shorter, more manageable hops. Folegandros lies twenty-two miles northwest and is the smallest of the big-name Cyclades stops, all the better for it. Karavostasi is the only real port, a modest place open to the south but well tucked in when the wind holds its usual northerly slot. You'll either take a stern-to berth or anchor off, depending on what's free when you arrive. The Chora sits high on a clifftop above the harbour, reached by taxi or a stiff half-hour climb, and it is worth every step of it: a lantern-lit maze of squares that feels a world away from Santorini's crowds. Dinner up there, with the drop to the sea below, is the evening's reward.

Things to do

Climb to the cliff-edge Panagia church

Swim the boat-only cove at Katergo

Matsata pasta with goat ragù

Walk the kalderimi to Ano Meria

Mooring tip

Karavostasi is stern-to at €25-40 with only a handful of slots; when full, anchor just east of the port in sand at 4-7 m. Stay clear if any southerly is forecast, as the harbour is fully open that way.

Milos
9
Day 9

Folegandros → Milos (Adamas)

Another twenty miles of beating northwest, the Meltemi square on the bow, so plan on a couple of long tacks and a slower average than the downwind days gave you. The payoff is Adamas, tucked right at the head of Milos's deep natural inlet. Once you're inside the bay the wind falls away and the shelter is about as complete as you'll find anywhere in the western Cyclades. Break the passage with a stop at Sarakiniko if the day is quiet; the white volcanic rock there looks like something off another planet, though the anchorage is exposed and only sensible in light air. Milos rewards a slower look than one night allows, but Adamas puts you within easy reach of Plaka's castle hill and the painted boathouses at Klima for a first taste.

Things to do

Swim beneath the lunar cliffs of Sarakiniko

Snorkel the Papafragas sea caves

Up to Plaka Castle for the view

Photo walk the Klima boathouses

Mooring tip

Stern-to on Adamas town quay, €30-50 a night, with reliable shelter from every direction. Pollonia in the northeast is cheaper but lies open to the northerly Meltemi, so save it for settled spells.

Kamares
10
Day 10

Milos → Sifnos (Kamares)

An easy eighteen miles north brings you to Sifnos, and Kamares on the west coast is the natural place to stop. The bay shelters you nicely from the north and northeast, but it does open to the west, so in late-summer spells when the Meltemi carries a westerly slant a swell can work its way in and make the night rolly. That's your cue to shift round to Platys Gialos on the south coast. Sifnos is, by common agreement, the eating island of the Cyclades: chickpea revithada baked slow overnight in a wood oven, lamb mastelo sealed in clay pots, a whole cooking tradition traced back to a local nineteenth-century chef. Come hungry. The clifftop monastery at Chrysopigi, out past Faros, is the walk to earn your dinner.

Things to do

Walk to Chrysopigi monastery past Faros

Lamb mastelo in clay pots at Artemonas

Visit a working pottery in Vathy

Swim the calm water at Vathi Bay

Mooring tip

Anchor on sand at 5-8 m in Kamares, or take one of the few stern-to slots on the small quay for €20-30. When the wind clocks into the west, move round to Platys Gialos on the south side.

Serifos
11
Day 11

Sifnos → Serifos

A gentle fourteen miles separates Sifnos from Serifos, but the anchorage asks for more care than the passage. Livadi Bay faces straight into the Meltemi and works like a funnel, and while the sand holds well, the wind can stretch out even a well-set anchor. Dragging is the classic Serifos mishap. Lay plenty of scope, dive the anchor to see it dug in properly, and don't wander off ashore in the first hour until you're sure it's holding. Above the port, the Chora ranks among the prettiest hill towns in the islands, a white cascade of houses climbing to a ruined castle. Get up there on the old donkey path or by road taxi and time it for sunset, when the windmills on the ridge catch the last of the light.

Things to do

Walk the donkey path up to Chora

Chickpea revithada in a village kafeneio

Swim at Psili Ammos beach

Sunset by the ridge-top windmills

Mooring tip

Two choices at Livadi: let the hook go on sand in 5-8 m with plenty of scope, or take the town quay stern-to for €20-30. Once it's blowing past 22 knots, dragging becomes a genuine worry, so free-dive the anchor before you leave the boat.

Serifos
12
Day 12

Serifos → Kythnos (Merichas)

Kythnos flies under the radar next to its famous neighbours, which is exactly its charm. Fifteen miles north of Serifos, it has none of the crowds and one genuinely special spot: Kolona, a couple of miles up the coast from the little ferry port at Merichas. A narrow ribbon of sand, maybe two hundred metres of it, links the islet of Agios Loukas to the main island, so you get a beach with sea on both sides and shallow, clear swimming whichever way you look. This is a place to drop the hook and stay put. Anchor off, swim until the light softens, and let dinner happen aboard as the day boats thin out. If the legs want stretching, the ridge road up to Dryopida makes a good cycle, and Loutra has thermal springs to soak tired shoulders.

Things to do

Anchor and swim at the Kolona sandbar

Soak in the Loutra hot springs

Cycle the ridge road to Dryopida

Sfougato cheese pie in a Dryopida taverna

Mooring tip

Anchoring at Kolona is free, on sand at 4-6 m, and the islet screens you from the northerly Meltemi. Merichas town quay is the paid stern-to fallback at €20-30, and Loutra has both thermal springs and a few marina berths.

Alimos
13
Day 13

Kythnos → Athens (Alimos)

The last real sailing day is the biggest single hop of the fortnight, thirty-five miles west-northwest back across the open Saronic. Get away early. With the Meltemi behind the beam it can be a glorious downwind run, but the wind is fickler out here than in the islands, and on a soft day you'll be motor-sailing to make a sensible arrival by late afternoon. Cape Sounion lifts over the bow about halfway across, the temple columns marking the turn in toward Athens, and after a fortnight in the Cyclades it feels like the gate closing behind you. Duck in at the fuel berth to top up the tanks before you take your berth at Alimos, so the boat is fuelled and ready for the base come morning. Save the last night for a long crew dinner in Glyfada.

Things to do

A last swim below the Sounion temple

Refuel and rinse down at Alimos

Crew dinner in a Glyfada taverna

Souvenir stop on the Faliro promenade

Mooring tip

Take a stern-to berth on lazy lines at Alimos Marina, €70-100 a night, and refuel at the entrance fuel berth before you moor. Confirm your handover slot with the base 24 hours ahead.

Athens
14
Day 14

Athens (Alimos) → Athens (Check Out)

The last morning is a gentle one. Have the boat cleared and ready for handover before nine, when someone from the base will walk round it with you, checking her over while you're there to answer for anything. Assuming nothing is flagged, the security deposit comes back to you within a week or so. The airport is only twenty-five minutes up the road from Alimos, though on a Friday it pays to allow a full hour for the traffic. There's no need to rush the goodbyes. Grab a last frappé and a plate of something on the Glyfada seafront while the bags are loaded, and settle up with the dock hands if they looked after you well. Two weeks and a good stretch of the Cyclades behind you, it's a fine place to finish.

Things to do

Final walk-round with the base manager

Frappé on the Glyfada promenade

Transfer to the airport, 25 minutes

Tip the dock crew for good service

Mooring tip

Hand the boat over at Alimos before nine. The deposit is normally released within seven days of the inspection; photograph and agree any damage notes before you sign anything off.

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