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

Paros via Milos & Santorini.

Two weeks under sail from Paros: Naxos, the Small Cyclades, Santorini, Milos, Sifnos, Kythnos and Syros before the run home. A full Cyclades circuit.

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.

Naxos
Day 1

Paros → Naxos

A gentle six-mile warm-up east to Naxos, where the marble Portara frames the sunset and the town quay forgives beginners.

Distance

11 NM

Sailing

~2.2h 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
Naxos
1
Day 1

Paros → Naxos

Six miles is barely a passage, and that is the point on day one. You clear Paros, settle the crew into the winches, and Naxos town opens up before anyone has found their sea legs. The harbour holds you steady whatever the wind does, so this is the night to relax rather than fuss over ground tackle. Ashore, walk out to the Portara at dusk. It is a single marble doorway left standing from a temple to Apollo that was never finished, and the low sun behind it does the rest. With a spare morning, the climb up Mount Zas takes about four hours and lays the whole island out below you. Down in Halki, the old distilleries pour kitro, a citron liqueur you will not find bottled anywhere else.

Things to do

Watch sunset through the marble Portara

Climb Mount Zas, Zeus's birthplace (4h)

Taste kitro citron liqueur in Halki

Swim the sands at Agios Prokopios

Mooring tip

Stern-to on the Naxos town quay, roughly EUR 30-50 a night, and it shelters from every direction. Even in August you will usually find a slot without racing for it.

Donoussa
2
Day 2

Naxos → Donoussa

Twenty-four miles east-southeast puts real distance between you and the crowds. Donousa has around a hundred permanent residents, and once the afternoon ferry leaves, the island belongs to whoever stayed. Aim for the little quay at Stavros, but keep the anchor ready; slots are few, and dropping the hook in the bay outside is no hardship at all. Kedros Beach sits a short walk south of the village, the water shading from milk to deep blue over pale sand. Walkers can follow the track up to Kalotaritissa, a cluster of stone houses that looks unchanged in decades. For lunch, look for gouna, mackerel split and dried in the sun then grilled over coals at a beach shack. Simple, salty, exactly right after a passage.

Things to do

Long swim at Kedros Beach

Hike up to Kalotaritissa stone hamlet

Snorkel into the Cave of the Wall

Sun-dried gouna grilled at a beach shack

Mooring tip

Berthing stern-to at Stavros costs EUR 15-25, but the few slots fill fast; if you miss out, the bay just outside holds well on sand in 5-7 m. Either choice keeps the northerlies off you.

Amorgos
3
Day 3

Donoussa → Amorgos (Aegiali Harbor)

Amorgos earns its reputation the moment Hozoviotissa comes into view, an eight-storey monastery from 1088 pressed flat against a cliff that drops straight to the sea. Getting up there means around three hundred steps from the road, and the monks still hand visitors a shot of psimeni raki at the top. Wear something that covers knees and shoulders or you will be turned back. Aegiali, up on the north coast, gives good shelter when the Meltemi blows; if it swings south, run round to Katapola instead. Divers can drop onto the Olympia wreck off Liveros, the ship from the Besson film that made this island famous. Evenings belong to the hill village of Tholaria, where slow-cooked goat comes to the table without ceremony.

Things to do

Climb the 300 steps to Hozoviotissa

Dive to the Olympia wreck at Liveros

Goat and psimeni raki in Tholaria

Follow the ridge path above Aegiali

Mooring tip

Aegiali takes you stern-to for EUR 25-40 and shelters from the north. When the wind clocks into the south, shift to Katapola on the other side of the island.

Koufonissi
4
Day 4

Amorgos → Koufonissi

Koufonissi is small and knows its worth, so plan to arrive early. The village and quay sit on Pano Koufonissi; the sister islet across the strait, Kato Koufonissi, is empty apart from a chapel and a taverna that opens in season. Between them lies Pori, a shallow lagoon where the water turns an almost unreal turquoise over white sand. Anchor off it for a long lunchtime swim. The southeast coast is cut with low cliffs and sea caves worth exploring with a mask and fins. Back on the quay come evening, order astakomakaronada, lobster broken into a tangle of spaghetti, the dish every second table seems to be sharing. Walk it off through the whitewashed lanes before the night ferries reshuffle the harbour.

Things to do

Anchor and swim in Pori lagoon

Snorkel the southeast coast sea caves

Astakomakaronada lobster spaghetti for dinner

Wander Pano Koufonissi's whitewashed lanes

Mooring tip

Stern-to on the Pano Koufonissi quay costs EUR 25-40, but the slots are usually gone by 17:00. If it is full, anchor on sand at 4-7 m just east of the village.

Schoinousa
5
Day 5

Koufonissi → Schoinousa

Barely five miles separate Schoinousa from Koufonissi, but they feel like different decades. Two hundred people live here, most of them up in Chora, the single hilltop village reached by a short climb from the harbour at Mersini. There is no rush to anything. Tsigouri Beach lies just around from the port, tucked in enough to stay calm when the north wind is up, and the swimming is easy over sand. In the village, find a taverna table under a tamarisk and order tomato keftedes, fritters of grated tomato, onion and herbs fried until the edges catch. Walkers with an afternoon to spare can follow the path out to the little mountain church of Panagia for a view that takes in half the archipelago.

Things to do

Swim sheltered Tsigouri Beach near the port

Climb to Chora on the ridge

Tomato keftedes at a village taverna

Walk out to the Panagia church

Mooring tip

Mersini takes you stern-to for EUR 15-25, though the slots are limited. Failing that, anchor on sand at 4-6 m just east of the harbour, well sheltered from the north.

Irakleia
6
Day 6

Schoinousa → Irakleia

If you want to know what the Cyclades felt like fifty years ago, Irakleia is the answer. A hundred people, one road, one taverna doing dinner, and a pace that slows you down whether you planned it or not. Most crews drop the hook in Agios Georgios bay rather than fight for the short quay. Livadi beach, a walk from the harbour, holds water so clear the anchor chain reads like it is hanging in air. Give yourself half a day for the hike to the Blue Cave, roughly thirty minutes from the village and worth the scramble when the light comes through the entrance. Up above, the ruined kastro from the pirate years is a quiet place to watch the sun go down.

Things to do

Hike thirty minutes to the Blue Cave

Swim the clear water at Livadi

Grilled gouna at the island's one taverna

Walk up to the pirate-era kastro

Mooring tip

For the quietest night, drop the hook on sand in Agios Georgios bay at 5-7 m, where the northerlies can't reach. Quay berths are scarce, EUR 15-25 with no lazy lines, so pack a pair of good long stern warps.

Vlychada
7
Day 7

Irakleia → Santorini (Vlychada Marina)

This is the biggest day of the fortnight, thirty-two miles south down the channel with the Meltemi usually giving you a fast, steady reach. Break it with a swim at Manganari on the south coast of Ios if the timing works. Aim to raise Santorini with plenty of light left, because the caldera is far too deep to anchor and the marina at Vlychada is the only sensible berth. Get in before five and you have the evening for the island. A taxi up to Oia buys you the famous cliff-edge sunset, though the crowds are real; the wineries are the quieter pleasure. Santo Wines and Domaine Sigalas both pour the crisp, mineral Assyrtiko the volcanic soil produces. Order fava with capers somewhere in Megalochori.

Things to do

Sunset from the cliffs at Oia

Assyrtiko tasting at Santo Wines or Sigalas

Swim the volcanic Red Beach

Order fava with capers in Megalochori

Mooring tip

Vlychada Marina is stern-to at EUR 60-100 a night and must be booked ahead in high season. The caldera runs over 300 m deep, so anchoring off the towns is simply not an option.

Folegandros
8
Day 8

Santorini → Folegandros

Folegandros is where the wind turns honest. Twenty-two miles northwest with the Meltemi on the nose means a proper beat, so leave early and be ready to tack. The reward is one of the finest Choras in the islands, perched on a cliff edge two hundred metres above the port and reached by a stiff half-hour up the old kalderimi. Karavostasi, the harbour, shelters well from the north but turns nasty in a southerly, so read the forecast before committing. Katergo, a strip of shingle reachable only by boat or a long walk, is the swim of the day. Come evening, look for matsata, hand-rolled pasta under a goat ragu, served in one of the vine-shaded courtyards up in Chora.

Things to do

Climb the kalderimi to cliff-top Chora

Swim the shingle at Katergo cove

Hand-rolled matsata with goat ragu

Walk the old path to Ano Meria

Mooring tip

Karavostasi is stern-to at EUR 25-40 with limited slots, and it only works in northerlies; avoid it altogether when the wind is in the south. If the quay fills, anchor east of the port on sand at 4-7 m.

Milos
9
Day 9

Folegandros → Milos

Another twenty miles to windward, and then Milos rewards the effort. The long inlet leading to Adamas gives you the best-protected overnight anywhere in the western Cyclades, which matters when the Meltemi is running hard outside. Tuck up at the town quay and let the crew off to explore. Sarakiniko is the sight everyone comes for, a headland of wind-smoothed white rock that could pass for the surface of the moon; swim there only when the wind lies down, as it is wide open. Snorkel the Papafragas caves, then climb to Plaka Castle late in the day for a view down the whole gulf. Down at Klima, the fishermen's syrmata, boat garages painted every colour, make the best photo on the island.

Things to do

Swim the white moonscape at Sarakiniko

Snorkel the Papafragas sea caves

Climb Plaka Castle for the panorama

Photograph the Klima syrmata boat garages

Mooring tip

Stern-to on the Adamas town quay costs EUR 30-50 and holds you steady in any wind. Pollonia on the northeast coast is cheaper but lies exposed when the Meltemi blows from the north.

Vathi
10
Day 10

Milos → Sifnos

Sifnos is the kitchen of the Cyclades, the home island of the cookbook writer Nikolaos Tselementes, and you eat well here without trying. Anchor decisions come down to wind: Vathi on the south coast is the calmest hole to swing in, while Kamares on the west gives you a bigger paid quay. If the breeze clocks round to the west, move to Vathi and sleep easy. The signature dish is mastelo, lamb or goat slow-baked with wine and dill in a sealed clay pot, best eaten up in Artemonas. Walk out to Chrysopigi, the small monastery on its own rocky spit by Faros, at the golden hour. Vathi still keeps a couple of working potteries turning out the local clay.

Things to do

Mastelo clay-pot lamb in Artemonas

Sunset at Chrysopigi monastery, Faros

Visit a working pottery in Vathi

Swim the calm water of Vathi Bay

Mooring tip

Vathi gives good holding on sand at 4-6 m and stays calm; alternatively the Kamares quay is stern-to at EUR 20-30. When the wind backs into the west, Vathi is the safer bet.

Kythnos
11
Day 11

Sifnos → Kythnos (Loutra)

This is a working day, thirty-two miles north into the wind, so plan on two long port tacks and get away early. Break the leg at Serifos if you can, dropping anchor off Vagia for a lunch swim while the beach stays sheltered from the south. Then push on to Kythnos. The prize at Loutra is unusual: natural thermal springs that surface right at the harbour and warm the shallows where they meet the sea. Soak after the day's sailing. With extra time, the Kolona sandbar on the northwest tip is a short detour to one of the loveliest anchorages in the group, a tombolo of sand joining two islands. Inland, the old capital Driopida hides tavernas doing sfougato, a baked cheese pie.

Things to do

Soak in the Loutra thermal springs

Lunch swim off Serifos at Vagia

Detour to the Kolona tombolo swim

Baked sfougato cheese pie in Driopida

Mooring tip

Loutra takes you stern-to for EUR 25-40 with lazy lines and shelters from the north. If it is full, Merichas on the west coast is the fallback.

Paros
12
Day 12

Kythnos → Syros

Syros comes as a surprise after two weeks of small islands. Ermoupoli was the great port of Greece in the nineteenth century, and its wealth still shows in the marble, the opera house and the neoclassical facades stacked up the two hills behind the harbour. The town quay is about the easiest stern-to berth you will find in the Cyclades, so even in a blow this is a relaxed arrival. Climb to Ano Syros, the medieval Catholic quarter on the higher hill, for lanes barely wide enough for a donkey and a long view over the roofs. The island is famous for loukoumi, so buy a box from one of the old confectioners. End the day on Plateia Miaouli, the marble square, as the cafes fill.

Things to do

Climb to the Ano Syros Catholic quarter

Taste loukoumi at an old confectioner

Sit on Miaouli marble square at dusk

Swim the rock platforms at Asteria

Mooring tip

The Ermoupoli town quay is free and needs your own anchor, and it shelters well from any direction. If it fills up, the Manna marina charges EUR 60-80 a night.

Paros
13
Day 13

Syros → Paros

The last real sailing day brings you back to Paros on a comfortable beam reach, twenty-four miles southeast. You have a choice of ends: Naoussa, the small fishing harbour on the north coast that fills every camera on the island, or Parikia, easier to get into if the crew is tired. Most people pick Naoussa for the last night. Save an hour for Kolymbithres, where wind and sea have carved the granite into smooth grey outcrops you can snorkel around. In the evening, take a table on the Naoussa pier where the boats still land octopus and hang it on a line to dry before it goes on the grill. If there is time, the marble lanes of Lefkes make a quiet inland detour.

Things to do

Snorkel the wind-carved rocks at Kolymbithres

Grilled octopus on the Naoussa pier

Wine tasting at a Marpissa vineyard

Walk the marble lanes of Lefkes

Mooring tip

Naoussa is stern-to at EUR 30-50 but often full by 17:00, so plan to arrive by mid-afternoon. Plastira Bay half a mile east gives good holding on sand at 5-7 m, and Parikia is the larger fallback.

Paros
14
Day 14

Paros → Check-out

Handover is the unglamorous end to a fine fortnight. Bring the boat alongside at Parikia or Naoussa before nine, have the tanks full and the gear stowed, and walk the base manager through her while the crew packs. Do it cleanly and the deposit comes back within about a week. There is usually still time for a proper breakfast on the Parikia waterfront before anyone thinks about transfers. If the flight is later in the day, a taxi out to Golden Beach on the east coast buys one last swim, the long sweep of sand that windsurfers favour for its steady afternoon breeze. Paros airport is barely fifteen minutes from Parikia, so nobody needs to rush.

Things to do

Walk the handover with the base manager

One final swim at Golden Beach

Breakfast on the Parikia waterfront

Fifteen-minute transfer to Paros airport

Mooring tip

Be alongside at Parikia or Naoussa before 09:00 for the inspection. Leave the boat clean and fuelled and the deposit is usually released within seven days.

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