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.
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.
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
Route at a glance
Route summary
Click any day to jump back to the map and see its photos, narrative, and mooring tip.
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.
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.
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.
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.
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.
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.
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 → 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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