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Route · 14 days · one-wayYacht charter route · Cyclades

Paros via Siros & Milos.

A 14-day round-trip from Paros through Sifnos, Syros, Mykonos, Naxos, Ios, Santorini, Folegandros and Milos: the full Cyclades grand tour.

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.

Kamares
Day 1

Paros → Sifnos (Kamares Harbor)

The first leg runs southwest to Sifnos, a 20-mile settling-in sail to the island Greeks rate above all others for its cooking.

Distance

22 NM

Sailing

~4.4h 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

Paros

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
Kamares
1
Day 1

Paros → Sifnos (Kamares Harbor)

Sifnos sits about twenty miles off the bow, and the passage down gives everyone a chance to find their feet before the harder legs later in the trip. Kamares, the ferry port on the west side, is the natural place to spend the night. It tucks in well against the northerlies but stays open to the west, so keep an eye on any afternoon shift. Ashore, this is the island that taught Greece to cook. The inland villages of Apollonia and Artemonas are a short bus ride up, and the slow-baked meat in clay pots is worth the trip. We usually leave the boat by mid-morning to have the light for the walk out to Chrysopigi. Book nothing; just anchor and swim.

Things to do

Slow-baked lamb in clay pots at Artemonas

Walk to Chrysopigi monastery above Faros

Coffee in the Apollonia lanes at dusk

Swim the sandy bay at Platis Gialos

Mooring tip

Sand holds well in 5-8 m across Kamares Bay; the small quay takes a stern-to line for roughly 20-30 euros a night. Should the breeze swing west and roll swell in, move round to Vathi.

Serifos
2
Day 2

Sifnos → Serifos (Livadi)

Serifos is a short jump, so there's time for a lazy morning on Sifnos before slipping the lines. Livadi Bay opens to the southeast and can accelerate the Meltemi straight down its throat, which makes the holding your main concern rather than the sail in. Set plenty of chain, then dive on the anchor before you relax; boats drag here more than most crews expect. The reward is the town overhead. Chora stacks white cubes up the ridge, and the old stone path climbing to it takes about half an hour on foot. Up top there are windmills, a couple of quiet kafeneia, and a view back down over the whole bay. Order the chickpea stew if the kitchen has it going that day.

Things to do

Climb the old stone path to Chora

Revithada chickpea stew at a kafeneio

Sunset by the windmills above town

Swim the fine sand at Psili Ammos

Mooring tip

Anchor in Livadi Bay on sand in 5-8 m and lay out long scope; the town quay takes stern-to lines for 20-30 euros. Once it blows past the low twenties the bay gets nervous, so dive the anchor before heading ashore.

Kythnos
3
Day 3

Serifos → Kythnos (Loutra)

Break the leg north with a stop at Kolona, the thin ribbon of sand that joins Kythnos to the Agios Loukas islet. It shelves gently on both sides and gives cover from the north, so it makes a fine lunch anchorage and swim before you carry on. Loutra itself sits a few miles further up the coast. The thermal water that surfaces near the harbour has drawn people here since antiquity, and you can still feel the warm current where it meets the shallows. Stern-to in the harbour is straightforward with the laid lines. Inland, the linked villages of Chora and Dryopida reward an afternoon on a bike or in a hire car, with narrow lanes and a good taverna or two for the local cheese pie.

Things to do

Soak where the springs meet the sea at Loutra

Swim the double-bay sandbar at Kolona

Cycle the ridge between Chora and Dryopida

Sfougato cheese pie in a Dryopida taverna

Mooring tip

Take a stern-to berth in Loutra harbour on the laid lines, around 25-40 euros; it covers you from the north. When the wind has any south in it, Merichas on the west coast is the better bet.

Syros
4
Day 4

Kythnos → Syros

The run over to Syros is the longest so far, usually a comfortable beam reach in the standard summer northerly. Ermoupoli comes as a surprise after the smaller islands. It was the busiest port in Greece in the nineteenth century, and the money built an opera house, a marble town square, and tiers of pastel mansions rising up two hills. The waterfront berth is one of the easier ones in the islands to lie against, with good protection whichever way the wind sits. Give yourself the evening ashore. Climb the stepped lanes into Ano Syros, the old Catholic quarter, for the view and a bite; back down at sea level, the confectioners still turn out loukoumi and nougat by hand. Miaouli Square fills up pleasantly once the heat drops.

Things to do

Climb into Ano Syros, the Catholic quarter

Taste hand-made loukoumi at an old confectioner

Evening stroll across Miaouli marble square

Swim off Foinikas on the south coast

Mooring tip

Lie stern-to along the Ermoupoli waterfront on your own anchor at no charge, with shelter from every direction. If the quay is packed in high season, Manna marina nearby has berths for 60-80 euros.

Mykonos
5
Day 5

Syros → Mykonos (Tourlos Marina)

Mykonos lies a straightforward twenty-two miles east. If the crew is up for it, break the passage at Delos, the uninhabited island that was one of the great sanctuaries of the ancient world; you can day-anchor off it and walk the ruins, but the site shuts around sunset and no one stays the night. Push on to Tourlos, the newer marina just north of the main town, and put a booking in a day ahead when July and August fill it. The town needs no introduction. Away from the crowded lanes there's a quieter side worth finding: the fishing houses of Little Venice at dusk, the row of windmills above them, and empty sand at Agios Sostis on the north shore, which has no road down to it.

Things to do

Day-anchor off Delos and walk the ruins

Lunch on the sand at Agios Sostis

Little Venice waterfront as the sun drops

Walk the loop to Armenistis lighthouse

Mooring tip

Book a stern-to berth in Tourlos New Marina online, especially for July and August; reckon on 70-110 euros at peak. The old town quay only holds in light northerlies under about 18 knots.

Naxos
6
Day 6

Mykonos → Naxos

Naxos is an easy reach south, and the town harbour is one of the more dependable stern-to berths on the route, tucked behind its mole and sheltered from most angles. The island earns a full day. It grows its own food, makes its own cheese and citron liqueur, and rises to Mount Zas, the highest peak in the Cyclades and, if you believe the old stories, the cave where Zeus grew up; the walk up takes the better part of four hours. Down in the old town, lanes wind up through the Venetian kastro. The set-piece is the Portara, a great marble doorframe standing alone on the islet at the harbour entrance, left over from a temple that was never finished. Walk out to it as the light goes.

Things to do

Sunset through the Portara marble doorway

Climb Mount Zas, the peak of the Cyclades

Kitron citron liqueur tasting at Halki

Swim the long sand at Agios Prokopios

Mooring tip

Naxos town harbour is a reliable stern-to at 30-50 euros and holds up well whatever the wind does. There's usually room, so you rarely need to arrive early.

Ios
7
Day 7

Naxos → Ios

The reach down to Ios is short enough to build in a stop. Manganari, a string of sandy bays on the south coast, is the obvious one: sheltered from the north and made for an anchor lunch and a long swim. Round to Ormos afterwards for the night. Ios carries two reputations that rarely meet. By day it is farm tracks, empty beaches, and a windmill-topped Chora you can climb to on foot; up on the northern tip, tradition puts the grave of Homer at Plakotos, and there's a marked path out to it. After dark the same Chora turns into the loudest square in the Cyclades, and it doesn't get going until around eleven. Pick which version you want, or take both.

Things to do

Anchor and swim off Manganari on the south coast

Walk to Homer's supposed grave at Plakotos

Late-night music in the Chora square

Sundowners by the windmills above town

Mooring tip

Take a stern-to berth in Ormos harbour, 25-40 euros; use the Mylopotas anchorage for daytime only. Manganari gives good cover from the north for the lunch stop.

Vlychada
8
Day 8

Ios → Santorini (Vlychada Marina)

Leave Ios at first light. Santorini is only eighteen miles off, but the caldera deserves to be entered in good daylight, and the marina you're aiming for is the sole practical overnight. The bay is a drowned volcanic crater, hundreds of metres deep almost to the cliff foot, so dropping the hook is out of the question; Vlychada, on the south coast, is where the boat stays. Book it well ahead in season. With the lines on, the island opens up above you. A taxi up to Oia gets you the famous cliff-edge sunset without fighting for a berth in the caldera, and the wineries inland pour a bone-dry Assyrtiko grown in low baskets against the wind. The volcanic soil shows up on the plate too, in the fava and the little tomato fritters.

Things to do

Taxi up to Oia for the cliff-top sunset

Assyrtiko tasting at Santo Wines or Sigalas

Fava and tomato fritters in Megalochori

Swim below the cliffs at Red Beach

Mooring tip

Vlychada on the south coast is effectively the only overnight; take a stern-to berth for 60-100 euros and book it well ahead in high season. The caldera itself is too deep to anchor.

Santorini
9
Day 9

Santorini → Santorini

Keep the boat at Vlychada and give the island a day on its own. The obvious anchor for the morning is Akrotiri, the town that a volcanic eruption sealed under ash around 1600 BC and left almost intact, streets, drains and painted walls and all. It's the reason people call this the Cycladic Pompeii. In the afternoon, take the tender out into the caldera and cross to little Thirasia, the quiet island on the far rim, for lunch away from the crowds. Save the evening for the wine. The cliff-edge estates line up their Assyrtiko and sweet Vinsanto against a view that does half the work; Ammoudi Bay, down the steps below Oia, is the place for grilled fish once the sunset crowds thin out.

Things to do

Walk the ash-buried streets of Akrotiri

Tender across the caldera to Thirasia

Assyrtiko and Vinsanto at a cliff-edge estate

Grilled fish down at Ammoudi Bay

Mooring tip

Stay put at Vlychada for a second night rather than chasing an anchorage. The cruise-boat buoys over at Thirasia aren't dependable for a charter yacht.

Folegandros
10
Day 10

Santorini → Folegandros

Turning north again means putting the Meltemi on the nose, so this can be a wet, close-hauled slog of twenty-two miles; pick a lighter day for it if the forecast lets you. Karavostasi, the little port, gives fair shelter from the north but nothing from the south, so watch the wind direction before committing to the night. What you come for sits high above the harbour. Folegandros Chora runs along a cliff edge with a sheer drop to the water, and the church of the Panagia crowns the hill above it, reached by a zigzag of steps. The island stays gentler than its neighbours: a courtyard plate of matsata, the local hand-rolled pasta, under the plane trees, and a boat or a hard walk out to Katergo beach.

Things to do

Climb the steps to the Panagia church

Courtyard matsata pasta under the plane trees

Swim the pale pebbles at Katergo

Walk the old path out to Ano Meria

Mooring tip

Karavostasi has only a handful of stern-to slots at 25-40 euros; if it's full, anchor on sand in 4-7 m in the bay just east. Steer clear of the whole place in any southerly.

Milos
11
Day 11

Folegandros → Milos (Port Adamantas)

Another leg into the wind brings you to Milos, and the payoff is the anchorage. Adamas sits at the head of a huge bay that was once a volcano's crater, and it may be the most sheltered water anywhere in the western Cyclades; whatever the Meltemi is doing outside, it's usually calm in here. The island is the strange one of the group. Sarakiniko, on the north coast, is a field of wind-smoothed white rock that looks more like the moon than a beach, best visited by tender on a still day. Further round there are half-drowned sea caves at Papafragas and the pirate hideout of Kleftiko to the southwest. Ashore, climb to the castle at Plaka for the long view, and find the painted boat-garage doors down at Klima.

Things to do

Tender to the white rock at Sarakiniko

Snorkel the sea caves at Papafragas

Climb to Plaka castle for the panorama

Photograph the syrmata boat doors at Klima

Mooring tip

Lie stern-to on the Adamas town quay for 30-50 euros, where the shelter holds from every direction. Pollonia on the northeast is cheaper but exposed to the north, so keep it for calm nights.

Vathi
12
Day 12

Milos → Sifnos (Vathi Port)

Back to Sifnos, but a different corner of it. Vathi is a nearly enclosed bay on the southwest, with a sandy bottom that holds an anchor beautifully and almost no swell to speak of; after the exposed legs of the past few days, it's a relief to arrive somewhere this quiet. The village behind the beach has made pots for generations, and a couple of workshops still fire their kilns by the water, so there's usually something to watch and something to carry home. Spend the afternoon in the shallows and eat at one of the handful of tavernas along the sand. If the wind swings and the anchorage loses its charm, Kamares round the coast has a proper paid quay to fall back on.

Things to do

Watch a potter fire the kiln at Vathi

Swim the flat calm of Vathi Bay

Taverna lunch on the sand at Vathi

Taxi over to the Chrysopigi monastery

Mooring tip

Anchor on sand in 4-6 m in Vathi, where you're shut in from just about everything. If you'd rather a quay, Kamares up the coast takes a stern-to line for 20-30 euros, though it opens to the west.

Paros
13
Day 13

Sifnos → Paros

The last real sailing day is a kinder one, twenty miles northeast with the wind on the beam rather than the bow. Aim for Naoussa on the north coast, where a small fishing harbour with the stub of a Venetian fort in the water makes about as pretty a final berth as the Cyclades offers; Parikia, the capital, is the simpler option if you'd rather an easy tie-up. Naoussa is the place for a proper last supper. Fishermen still land the catch at the quay, the tavernas grill octopus that's been drying on a line all afternoon, and the lanes fill up slowly after dark. Earlier on, there's time for a swim among the sculpted granite of Kolymbithres, a short hop across the bay.

Things to do

Swim the sculpted granite at Kolymbithres

Grilled octopus on the Naoussa quay

Wine tasting at a Marpissa vineyard

Dusk walk on the Lefkes marble lanes

Mooring tip

Naoussa's harbour takes stern-to lines for 30-50 euros but often fills by late afternoon, so aim to be in by five. Plastira Bay half a mile east anchors on sand in 5-7 m; Parikia is the roomier fallback.

Mykanos
14
Day 14

Paros → Check-out

Handover is usually before nine, so there's little to do but tidy the boat and be ready when the base manager comes aboard. The inspection runs through the hull, the engine hours and the inventory; assuming all is well, the security deposit comes back to your card within about a week. Paros airport sits down near Alyki in the south, only a quarter of an hour from Parikia, which makes the getaway painless. If the flights are later in the day, there's no rush. Take a slow breakfast on the Parikia waterfront while the ferries come and go, and if the timing works, drive across for one last swim on the long sandy stretch at Golden Beach before the transfer. Two weeks and the whole of the Cyclades behind you.

Things to do

Final walk-through with the base manager

Last swim on the sand at Golden Beach

Slow breakfast on the Parikia waterfront

Fifteen-minute transfer to Paros airport

Mooring tip

Have the boat alongside and cleared before nine for the handover. Once the inspection is signed off, the deposit is released back to your card inside a week.

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