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

Santorini via Mykonos & Milos.

Round-trip yacht charter from Santorini: Milos, Sifnos, Syros, Tinos, Mykonos, Amorgos, the Small Cyclades and Naxos across two weeks of Aegean sailing.

The route

Day-by-day route

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Day 1

Santorini (Vlychada Marina) → Folegandros

A 22-mile beat northwest into the Meltemi, landing at Folegandros where the Chora perches high above the little port of Karavostasi.

Distance

30 NM

Sailing

~6h 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

Santorini

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

Day 1

Santorini (Vlychada Marina) → Folegandros

Stock the boat at Vlychada first thing, because once you clear the breakwater the wind is on the nose and it stays there. Twenty-two miles of close-hauled sailing sets the tone: this itinerary front-loads the hard work so the second week runs downhill. Karavostasi is the only real harbour on Folegandros, a modest curve of quay tucked under the southeast cliffs. It holds up well when the wind sits in the north and turns nasty when it swings south, so read the forecast before you commit to the night. The village worth seeing is Chora, two hundred metres overhead, either a taxi ride or a sweaty half-hour up the old stone kalderimi. Break the passage with a swim at Katergo, a pale-pebble cove you can only reach from the water.

Things to do

Swim into Katergo cove by dinghy

Climb the kalderimi to Chora's clifftop

Try matsata pasta with goat in a courtyard

Walk out to Ano Meria's farmsteads

Mooring tip

Stern-to on Karavostasi quay runs €25-40 and fills fast; if there's no room, drop anchor east of the harbour on sand in 4-7 m. Clear out if a southerly is coming, the port has no protection from that quarter.

Day 2

Folegandros → Milos (Adamantas Port)

Another day hard on the wind, but the reward comes at the finish. Milos is really a drowned volcanic crater, and the entrance funnels you into a huge inner gulf where the sea flattens and the breeze fades to nothing. Adamas sits right at the top of that inlet and stays quiet whichever way the wind blows, which is why crews exhale here. Time the approach to pass Sarakiniko on the north coast: chalk-white rock scoured into ridges and hollows, more moonscape than beach. It only works as a swim stop in settled air, so grab it while the sea is flat. Ashore, the painted boathouses of Klima and the castle lookout at Plaka fill an easy afternoon once you have tied up.

Things to do

Swim the white ridges of Sarakiniko

Snorkel the Papafragas sea caves

Climb to Plaka Kastro for the view

Photograph the syrmata boathouses at Klima

Mooring tip

Tie stern-to along the Adamas town quay for roughly €30-50, with shelter from any direction you could ask for. Pollonia in the northeast costs less but takes the full force of a northerly Meltemi.

Day 3

Milos → Paros (Parikia)

The longest single day of the fortnight, so leave early. Vathi on the southwest corner of Sifnos makes the natural halfway halt, a near-landlocked bay with a little monastery on the sand and holding good enough for a lazy lunch swim. From there it is another eighteen miles up to Parikia. Naoussa gets all the postcards, but Parikia is the sensible overnight: the harbour is dredged, the stern-to is honest, and you are not fighting a dozen other boats for a slip at dusk. Wander into the old town after you have secured the boat and you will find the Ekatontapiliani, a squat Byzantine church going back to the fourth century, its courtyard cool even in August. The marble lanes behind it are worth an unhurried hour.

Things to do

Lunch swim in Sifnos's Vathi bay

Step inside the fourth-century Ekatontapiliani

Wander Parikia's marble old-town lanes

Dinner on the Parikia harbourfront

Mooring tip

Parikia's harbour takes stern-to at €30-50 and is far kinder than Naoussa when it comes to finding a berth. If you want the classic fishing-port scene, Naoussa is the trade-off, expect to arrive early and queue for space.

Day 4

Paros → Paros

No miles to log today, which frees the morning for the dull-but-necessary jobs: laundry, water, a proper provisioning run in Parikia. Once that is behind you, motor across the channel and drop the hook off the east side of Antiparos, a calm cove facing the strait with sand at four to seven metres. The swim to remember, though, is Kolymbithres, round the headland from Naoussa, where wind and salt have carved the granite into smooth grey lobes you can clamber over. Landlubbers in the crew can hire bikes and grind up to Lefkes, an old capital set back in the hills, its paved lanes some of the prettiest on the island. Come evening, swap the anchor for a berth in Parikia or Naoussa.

Things to do

Anchor for lunch off east Antiparos

Clamber the granite lobes at Kolymbithres

Cycle inland to Lefkes village

Taste Moraitis wine in Naoussa

Mooring tip

Anchoring off Antiparos is free, on sand in four to seven metres; hold there only for the day. For the night, take a stern-to slot in Parikia or Naoussa and switch berths before the light goes.

Day 5

Paros → Syros

If the Meltemi behaves, this is the leg you will talk about afterwards. Twenty-four miles with the wind on the beam, the boat heeled and settled, Syros lifting out of the haze ahead. Ermoupoli's quay sits deep inside the harbour and makes an easy stern-to, a relief after a spirited crossing. The town itself is unlike anywhere else in the group. Once the shipping capital of Greece, it climbs the hillsides in tiers of faded marble and pastel plaster, with the Orthodox quarter on one crest and the Catholic town of Ano Syros on the other. Walk up Miaouli Square as the cafés fill, buy a box of the local loukoumi, and you understand why islanders here never quite left for Athens.

Things to do

Climb to Catholic Ano Syros

Buy loukoumi from an old confectioner

Take an evening coffee on Miaouli Square

Swim off the Asteria rock platforms

Mooring tip

The Ermoupoli town quay is free and you lie to your own anchor, with shelter that holds in almost any blow. If it is packed, the Manna marina nearby has serviced berths at €60-80.

Day 6

Syros → Tinos

Short does not mean gentle. The gap between Syros and Tinos squeezes the northerly and adds a good five knots to whatever the forecast promised, so a twenty-five-knot afternoon in high summer is routine rather than remarkable. Sail it fast on a beam reach, but plan to have lines ashore by four, before the swell stacks up at the harbour mouth. Tinos new port takes a stern-to on middling sand holding, so lay plenty of chain; when it really pipes up, the inner basin is calmer. Beyond the pilgrimage church, this is a quiet, workaday island of dovecotes and stonemasons. Drive up to Pyrgos, where marble has been carved for generations, then loop back through the boulder fields around Volax.

Things to do

Watch marble carving in Pyrgos

Wander the boulder field at Volax

Follow the dovecote trail near Tarabados

Order Tinos artichokes in a village taverna

Mooring tip

Stern-to in the new harbour costs €25-40, but the sand is only fair, so set the anchor hard and give it scope. When the Meltemi tops twenty-five knots, move into the inner small-craft basin.

Day 7

Tinos → Mykonos (Tourlos Marina)

A hop of eight miles, and half of it spent bracing. The Tinos-Mykonos channel runs a reliable few knots above the regional wind and kicks up a short, hard chop by early afternoon, so it pays to be moving early. In July and August, reserve a slot at Tourlos New Marina the day before; the old town quay is free but lies wide open to swell and only makes sense when the northerly stays under eighteen knots. With the boat settled, the day is yours. Anchor off Ornos or Psarou for a swim, then leave the boat and go find whatever version of Mykonos suits the crew, the Little Venice waterfront at sunset for some, the Armenistis lighthouse walk for others.

Things to do

Anchor-swim at Ornos or Psarou

Stroll Little Venice at sunset

Walk out to Armenistis lighthouse

Beach lunch at road-free Agios Sostis

Mooring tip

Tourlos New Marina runs €70-110 a night in season and needs booking online a day ahead. The free town quay is only safe below about eighteen knots of northerly, otherwise the swell makes it miserable.

Day 8

Mykonos → Mykonos

Give the engine a rest and let the day belong to Delos. The little island three miles west is one of the great archaeological sites of the Mediterranean, an entire sacred city left to the lizards, and you can sail across, anchor off the south side in five to eight metres, and be walking among the marble lions inside the hour. Three or four hours ashore covers the Apollo sanctuary, the mosaic floors and the theatre. Wardens clear everyone off by sundown, so there is no lingering. Back aboard, point the bow at the south coast and work along Paradise, Elia and Agrari as the mood takes you, winding up at Scorpios for a drink as the light drops.

Things to do

Day-anchor and tour ancient Delos

Find the Terrace of the Lions

Beach-hop Paradise, Elia and Agrari

Sunset drink at Scorpios

Mooring tip

Spend the night back at Tourlos as before. At Delos, anchor off the south shore in five to eight metres of sand, keep it a daytime stop only, and be off before the wardens close the site at dusk.

Day 9

Mykonos → Amorgos (Aegiali Harbor)

The longest reach of the second week, and the one that changes the mood of the trip. You leave the marquee islands astern and cross open water toward Amorgos, a long spine of rock at the eastern edge of the Cyclades where charter boats thin out and the anchorages go still. Aegiali on the north coast is the safer berth when the Meltemi blows from the north; Katapola, round on the south, is the fallback. The reason everyone comes is Hozoviotissa, a white monastery glued to a sheer ochre cliff a few miles south, reached by three hundred steps up from the road. Climb it in the cool of the evening. The divers among you will know Amorgos as the backdrop to a certain film about the deep.

Things to do

Climb the 300 steps to Hozoviotissa

Dive the Olympia wreck off Liveros

Hike the ridge to Tholaria village

Try psimeni raki in a Langada taverna

Mooring tip

Aegiali gives stern-to at €25-40 with cover from the north; if the wind swings south, cross to Katapola instead. Amorgos has few charter berths, so call ahead in July and August to be sure of a spot.

Day 10

Amorgos → Irakleia

This is the emptiest corner of the whole route. Irakleia is the smallest of the four inhabited Small Cyclades, and it wears its size plainly: a hundred or so residents, a single road, a scatter of tavernas around the harbour at Agios Georgios. The big-island crowds simply never make it out here. Anchor in the bay on good sand and let the pace slow to match the place. The one set outing is the Cave of Agios Ioannis, half an hour on foot above the village of Panagia, a proper limestone chamber you scramble down into with a torch. Otherwise the day is for swimming off Livadi, the best strip of sand in the group, and eating grilled fish where the boats come in.

Things to do

Hike to the Cave of Agios Ioannis

Swim off Livadi beach

Eat grilled fish at the harbour

Walk up to the old kastro

Mooring tip

Drop anchor in Agios Georgios bay on sand in five to seven metres, tucked out of the northerly. The few quay slots go for €15-25 but have no lazy lines, so be ready to lay your own.

Day 11

Irakleia → Naxos

Naxos is the outlier in this crowd of arid rocks: big, fertile, mountainous, with peaks over a thousand metres and valleys full of olive and citrus. The town harbour is well sheltered and takes a stern-to without drama, and there is usually room even at the height of summer. On the islet guarding the entrance stands the Portara, a lone marble doorway left over from a temple to Apollo that was never finished, and it is the spot the whole town walks out to at sunset. If you have the legs for it, Mount Zas behind Filoti is the highest point in the Cyclades and a four-hour climb. If you would rather taste than trudge, the Tragaea villages pour a citron liqueur found nowhere else.

Things to do

Watch sunset through the Portara

Hike Mount Zas above Filoti

Taste kitron liqueur at Halki

Swim the sands of Agios Prokopios

Mooring tip

Naxos town harbour takes stern-to at €30-50 and holds well in any wind, with more spare capacity than most stops on the route. No need to book, but arriving mid-afternoon secures the better berths.

Day 12

Naxos → Ios

Twenty miles south on a Meltemi reach, threading the channel below Naxos. Break the run at Manganari, a set of sandy bays on the south coast of Ios that stay sheltered when the north wind is up, then work back round to Ormos for the night. Ios has one reputation, and it earns it after dark: the Chora, strung along the ridge above the port, empties into its own alleys around eleven and turns into an open-air party that runs till dawn through the summer. It is not for everyone, and you can sit it out at anchor in the bay. But climb up for the sunset by the windmills at least once, when the crowds are still warming up and the light is on the water.

Things to do

Swim the bays at Manganari

Watch sunset by the Chora windmills

Climb to the reputed tomb of Homer

Wander the Chora's whitewashed lanes

Mooring tip

Take a stern-to slot in Ormos harbour at €25-40; the big Mylopotas beach is fine for a daytime anchor but untenable overnight in the Meltemi. Manganari gives good north-wind shelter for a lunch stop.

Day 13

Ios → Santorini (Vlychada Marina)

Eighteen miles closes the loop back to where it started. Break the passage at Thirasia, the small inhabited island on the western rim of the caldera, for a last proper swim in deep blue water. The caldera itself is a sight but not a berth: it drops away to more than three hundred metres almost at the cliff foot, so anchoring is out and the mooring buoys off Thirasia are not to be trusted with a charter boat overnight. Vlychada on the south coast is the only sensible place to lie, and it is where you hand back the boat in the morning. Book a taxi up to Oia for the cliff-edge sunset, and toast a fortnight that ran the full arc of the Cyclades.

Things to do

Swim the caldera edge off Thirasia

Taxi to Oia for the sunset

Taste Assyrtiko at Santo Wines

Crew dinner in cliff-top Megalochori

Mooring tip

Vlychada Marina takes stern-to at €60-100 and should be booked well ahead in peak season. Confirm your handover time with the base a day out, and get in before the afternoon swell sets into the entrance.

Day 14

Santorini → Check-out

Last morning, and it runs to a familiar script. Have the boat cleared and ready by nine for the handover, walk the inspection with the base manager aboard, and expect the deposit back within a week once everything checks out. Photograph anything that gets noted before you sign, just so there is no argument later. The airport at Santorini is a twenty-five-minute drive from Vlychada, which leaves time for one last ritual if your flight is not too early: a taxi over to Ammoudi, the little fishing cove below Oia, for a cold-water swim off the rocks and a plate of something grilled at a waterside table before you point yourselves home.

Things to do

Walk the handover inspection with the base

Photograph any noted damage before signing

Last swim at Ammoudi below Oia

Grilled lunch at an Ammoudi taverna

Mooring tip

Hand the boat back at Vlychada before nine, cleared and fuelled to the terms of your contract. Photograph any damage the manager records before you sign, and the deposit should clear within seven days.

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Santorini via Mykonos & Milos.

Day-by-day route

Santorini (Vlychada Marina) → Folegandros

Route at a glance

Route summary