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Route · 7 days · one-wayYacht charter route · Cyclades

Santorini via Milos & Paros.

Sail a week from Santorini through Ios, Paros, Serifos, Sifnos and Milos, then home. A southern-Cyclades loop of caldera cliffs and volcanic bays.

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.

Ios
Day 1

Santorini (Vlychada Marina) → Ios

An easy 18-mile warm-up north from Vlychada to Ios, where Ormos gives calm stern-to mooring and the whitewashed Chora rewards a climb at dusk.

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

7 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 / 7
Ios
1
Day 1

Santorini (Vlychada Marina) → Ios

Your first leg is a gentle one, eighteen miles of open water while the crew finds its feet and someone remembers where the winch handles live. Clear Vlychada, point the bow north, and Ios rises within a few hours. We usually aim for Ormos, the harbour tucked into the island's southwest corner, where stern-to holding is dependable and the ferry wash settles by evening. Mylopotas, a mile south, is the swim stop everyone photographs, though it turns rolly the moment the Meltemi fills in, so treat it as a lunchtime call rather than a berth. Ashore, the port stays sleepy until the switchbacks up to Chora deliver you into a maze of chapels and bars. Climb before sunset. The light off the windmills is worth the sweat, and the square only wakes later.

Things to do

Hike to Homer's tomb above Plakotos

Swim the sandy coves at Manganari

Climb to Chora's windmills at sunset

Lunch anchor off Mylopotas beach

Mooring tip

Berth stern-to at Ormos, roughly 25-40 euros a night, with good holding once the ferry traffic thins after dark. Use Mylopotas only by day; it becomes untenable overnight once the Meltemi sets in.

Paros
2
Day 2

Ios → Paros (Parikia Harbor)

This is the leg that reminds you the Meltemi has teeth. The channel between Naxos and Sikinos accelerates the northerly, and most days you will see the low twenties building to thirty as you cross it, so shorten sail before you commit rather than wrestling it later. Once past, the wind eases under Paros and Parikia opens up ahead. We prefer it to Naoussa for an overnight; the harbour has been dredged, berthing is calmer, and you are a short walk from the old town. Wander the marble lanes to the Ekatontapiliani, the fourth-century church at the heart of Parikia, then find a table for grilled fish as the ferries come and go. Save Naoussa for a lunchtime run if the crew wants the fishing-harbour postcard.

Things to do

Tour the 4th-century Ekatontapiliani church

Walk Parikia's marble old-town lanes

Anchor off Kolymbithres granite rocks

Wine tasting at a Naoussa cellar

Mooring tip

Go stern-to in Parikia, around 30-50 euros a night; the dredged basin makes it an easier berth than Naoussa in a fresh Meltemi. If you want Naoussa's harbour instead, arrive early, since its handful of quay spots fill fast in July and August.

Serifos
3
Day 3

Paros → Serifos (Livadi)

Thirty-two miles of beam reach in a settled Meltemi make this the big mileage day, so leave the berth early and let the boat do the work. Serifos sits low and dry on the horizon until Livadi opens on the south coast. The bay accelerates the wind coming over the ridge, but the sand underneath holds well if you give it scope. This is the leg where crews most often drag, usually from laying too little chain, so set the hook properly and swim down to check it before anyone heads ashore. Above the port, the Chora clings to its rock like something from a film set. Walk the old mule steps up rather than taking the bus; the view back over the anchored fleet at dusk is the reward. Down at sea level, Psili Ammos is a fine afternoon swim.

Things to do

Climb the mule steps to Chora

Swim Psili Ammos on the east coast

Chickpea revithada in a Livadi kafeneio

Sunset by the ruined Chora windmills

Mooring tip

Anchor on sand in Livadi Bay at 5-8 metres and lay plenty of scope; the wind funnels down the valley and holding turns marginal above 20 knots, so dive the anchor before leaving the boat. The town quay takes a few stern-to boats at 20-30 euros a night if you would rather tie up.

Kamares
4
Day 4

Serifos → Sifnos (Kamares Harbor)

After yesterday's slog, fourteen miles feels like a rest day. Roll south under a steady northerly and you will be anchored in time for a long lunch. Kamares, the ferry port on the west side, is the usual overnight and sits well protected from the north and northeast, though it opens up if the breeze backs into the west. When that happens, up anchor and run round to Vathi on the south coast, a near-landlocked sandy bay that stays calm in almost anything. Sifnos is where you eat properly. This is the island of clay-pot cooking: revithada baked overnight, chickpea soup, slow lamb in the mastelo pot, and honey-almond sweets. Book a table up in Artemonas or Apollonia, hire a scooter if you have the afternoon, and don't skip the walk out to the Chrysopigi monastery on its rock at Faros.

Things to do

Clay-pot revithada in Artemonas

Walk to Chrysopigi monastery at Faros

Anchor overnight in sheltered Vathi bay

Browse the potters' studios in Vathi

Mooring tip

Drop the hook on sand at 5-8 metres in Kamares, or take one of the few stern-to spots on the small quay for 20-30 euros a night. If the wind clocks into the west and Kamares starts to roll, move to Vathi on the south coast, which holds calm through most conditions.

Milos
5
Day 5

Sifnos → Milos (Adamantas Port)

Milos earns its place on this loop for two reasons: the swimming and the shelter. The run down from Sifnos is short and usually kind, which leaves the afternoon free. Weather permitting, ghost past Sarakiniko on the north coast for a swim, the white pumice folded into shapes that look poured rather than eroded. It is fully exposed, so only stop when the sea is flat. From there, the long inlet reaches deep into the island toward Adamas, one of the most protected harbours in these waters, calm whatever the Meltemi is doing outside. Tie up, then get ashore. Take a taxi or scooter up to Plaka for the castle view, and wander down to Klima, where the fishermen's boat garages line the shore in blocks of painted colour beneath the cliff.

Things to do

Swim the white cliffs of Sarakiniko

Snorkel the Papafragas sea caves

Climb to Plaka Castle for the view

Photograph the painted syrmata at Klima

Mooring tip

Berth stern-to on the Adamas town quay for around 30-50 euros a night; shelter here is excellent from every direction. Pollonia in the northeast is quieter and a little cheaper, but it sits open to a northerly Meltemi, so leave it for settled spells.

Vlychada
6
Day 6

Milos → Santorini (Vlychada Marina)

The final passage is the second-biggest of the week, thirty-eight miles southeast across open water, usually a comfortable beam reach in the prevailing northerly. Point at Santorini early and keep an eye on the clock. You want to be inside Vlychada before five, both to leave the evening free and because the marina berth is worth arriving to in daylight. Call ahead in peak season; the slots go quickly and you don't want to be circling at dusk. With the boat secure, hand the lines to someone and take a taxi north to Oia. The sunset there draws a crowd for good reason, and the walk down to Ammoudi afterwards puts you at a fish taverna by the water. If you would rather dodge the crush, the vineyards at Santo Wines or Domaine Sigalas pour a fine Assyrtiko.

Things to do

Taxi to Oia for the caldera sunset

Assyrtiko tasting at Santo Wines

Fish dinner down at Ammoudi Bay

Swim off the Red Beach cliffs

Mooring tip

Reserve a Vlychada berth well ahead in July and August; stern-to here runs 60-100 euros a night and the marina fills in peak weeks. Aim to be alongside by mid-afternoon, and confirm your handover slot with the base 24 hours out.

Paros
7
Day 7

Paros → Santorini (Check Out)

Last morning, and it's the tidy one. Have the boat back at Vlychada and cleared out before nine so the handover runs to schedule. Walk the inspection with the base manager rather than leaving them to it, and photograph anything already marked on the sheet before you sign; deposits usually clear within a week of a clean check-out. Once the paperwork is done, you have a little time before the transfer. The airport at Santorini sits about twenty-five minutes up the road, so there's room for a slow breakfast on the caldera rim or a final swim at Ammoudi Bay beneath Oia, where the water is deep and cool off the rocks. Then it's bags on the dock and the drive to JTR. A tight, satisfying loop of the southern and western Cyclades, done.

Things to do

Walk the check-out with the base manager

Final swim at Ammoudi Bay below Oia

Breakfast on the caldera rim

Transfer to Santorini airport (JTR)

Mooring tip

Have the boat alongside at Vlychada before nine for the handover; the deposit is typically released within seven days once the inspection is clean. Photograph any pre-noted damage before you sign, so nothing is disputed later.

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