Europe Yachts
— Route · 7 days · one-way
Yacht charter route · Cyclades

Santorini
via Milos & Paros.

Sail a 7-day yacht charter from Santorini through Ios, Paros, Serifos, Sifnos and Milos and back. Southern + western Cyclades loop combining caldera + lunar volcanic islands.

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The route

Day-by-day route

Click any pin on the map or any day in the Route summary below to see the daily stop, narrative, and photos.

Ios
Day 1

Santorini (Vlychada Marina) → Ios

18 nm shake-down north to Ios — first leg out of Vlychada. Ormos harbour is sheltered. Mylopotas swim is daytime only. Highlights: Hike to the supposed tomb of Homer above Plakotos and Swim Manganari Bay (south coast).

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 · Sat – Sat
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, restaurants, and route notes for every leg of the week — written by sailors who've actually run this passage.

Day 1 / 7
Ios
1
Day 1

Santorini (Vlychada Marina) → Ios

18 nm shake-down north to Ios — first leg out of Vlychada. Ormos harbour at the south end of Ios is sheltered and stern-to is reliable. The new marina is undergoing expansion. Mylopotas Bay 1 nm south is the standard daytime swim anchorage but unsafe overnight in any Meltemi.

Things to do

Hike to the supposed tomb of Homer above Plakotos

Swim Manganari Bay (south coast)

Late-night Chora rembetika square

Sunset drinks above the windmills

Mooring tip

Ormos harbour stern-to, €25-40/night. Mylopotas anchorage daytime only — untenable overnight in Meltemi.

Paros
2
Day 2

Ios → Paros (Parikia Harbor)

28 nm north on Meltemi reach. Naxos-Sikinos channel is the breeziest stretch of the leg — port-tack reach with steady 22-30 knots. Reef early. Parikia harbour is dredged and easier mooring than Naoussa. The 4th-century Panagia Ekatontapiliani sits in the centre of the old town.

Things to do

Visit the 4th-century Ekatontapiliani church

Sunset off Kolymbithres lunar rocks

Wine tasting at a Marpissa vineyard

Walk Parikia old town marble lanes

Mooring tip

Stern-to in Parikia harbour, €30-50/night, easier mooring than Naoussa. Naoussa is the alternative for the photogenic fishing-harbour scene.

Serifos
3
Day 3

Paros → Serifos (Livadi)

32 nm west to Serifos — long beam-reach leg in standard Meltemi. Livadi Bay on the south coast funnels the Meltemi but holds well on sand. Drag is the most common Serifos charter incident — set anchor with long scope, dive to verify.

Things to do

Walk the donkey path up to Chora

Revithada chickpea stew in a kafeneio

Swim Psili Ammos beach (south coast)

Sunset at the windmills above Chora

Mooring tip

Anchor in Livadi Bay on sand at 5-8 m, long scope mandatory. Stern-to on town quay, €20-30/night. Drag risk above 22 kn — dive the anchor before going ashore.

Kamares
4
Day 4

Serifos → Sifnos (Kamares Harbor)

14 nm short hop south to Sifnos. Kamares Bay on the west coast is the obvious overnight — sheltered from N and NE but opens to W. Switch to Vathi south coast when wind clocks west. Sifnos is the gastronomy island of the Cyclades.

Things to do

Walk to cliffside Chrysopigi monastery at Faros

Mastelo lamb in clay pots at Artemonas

Pottery workshop visit in Vathy

Swim Vathi Bay (south coast, calmest)

Mooring tip

Anchor on sand at 5-8 m in Kamares Bay or stern-to on the small quay (€20-30/night). Switch to Vathi south coast when wind clocks west.

Milos
5
Day 5

Sifnos → Milos (Adamantas Port)

18 nm south to Milos. The long Milos inlet provides one of the most sheltered overnights in the western Cyclades. Sarakiniko bone-white volcanic moonscape on the way past is the unmissable swim stop, but exposed and only viable in calm wind. Klima fishermen syrmata photo walk ashore.

Things to do

Swim stop at lunar Sarakiniko cliffs

Snorkel Papafragas sea caves

Visit Plaka Castle for the panorama

Klima fishermen syrmata photo walk

Mooring tip

Stern-to in Adamas town quay, €30-50/night. Excellent shelter in any wind direction. Pollonia northeast is cheaper but exposed in N Meltemi.

Vlychada
6
Day 6

Milos → Santorini (Vlychada Marina)

38 nm long beam-reach southeast back to Santorini. Vlychada Marina arrival before 17:00 for handover-prep evening. Caldera entry deserves daylight; book ahead for the marina slot in peak season. Last evening: taxi to Oia for the cliff-top sunset. Plan to taxi to Oia for the cliff-top sunset, wine tasting at Santo Wines or Domaine Sigalas, swim Red Beach (south coast access).

Things to do

Taxi to Oia for the cliff-top sunset

Wine tasting at Santo Wines or Domaine Sigalas

Swim Red Beach (south coast access)

Crew dinner in caldera-edge Megalochori

Mooring tip

Vlychada Marina stern-to, €60-100/night. Book ahead in peak season. Confirm handover slot 24h ahead with the base.

Paros
7
Day 7

Paros → Santorini (Check Out)

Handover at Vlychada before 09:00. Boat inspection — deposit released within 7 days. Crew transfer to Santorini airport (JTR) is 25 minutes by road. Photo evidence of any noted damage before signing. Plan to final inspection with the base manager and last swim at Ammoudi Bay below Oia.

Things to do

Final inspection with the base manager

Last swim at Ammoudi Bay below Oia

Breakfast at a caldera-edge café

Airport transfer (25 min from Vlychada)

Mooring tip

Hand over at Vlychada before 09:00. Deposit released within 7 days post-inspection. Photo evidence of any noted damage before signing.

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