— Route · 14 days · one-way

Yacht charter route · Cyclades

Santorini
via Mykonos & Milos.

Sail a 14-day yacht charter round-trip from Santorini through Mykonos, Amorgos, Naxos and Milos. Vlychada start avoids the Athens crossing — straight into the southern Cyclades.

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.

Day 1

Santorini (Vlychada Marina) → Folegandros

22 nm upwind northwest to Folegandros. Bear in mind the route starts upwind on day 1 — the long downwind leg is the back-half. Karavostasi sheltered N, exposed S.

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 · 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 / 14

Day 1

Santorini (Vlychada Marina) → Folegandros

Provisioning at Vlychada in the morning, lift lines after lunch. 22 nm northwest with the Meltemi on the bow — first day is also the first upwind work. Folegandros has only one practical port, Karavostasi, on the southeast coast. Sheltered from N, exposed S; check forecast for the second half of the week. Cliff-top Chora is 200 m above the harbour, accessed by taxi or a 30-minute climb up the kalderimi. Day-anchor at Katergo Bay (boat-only access) for a swim before mooring.

Things to do

Swim Katergo Bay (boat-only access)

Taxi to Chora for the cliff-edge Panagia church

Matsata pasta with goat ragù in a courtyard

Walk the kalderimi path to Ano Meria

Mooring tip

Karavostasi stern-to, €25-40/night, limited slots. Anchor in the bay east of port on sand at 4-7 m if full. Avoid in S winds — port fully exposed south.

Day 2

Folegandros → Milos (Adamantas Port)

20 nm northwest, second upwind day. Milos opens up at the long inlet entrance and the wind drops away once inside; Adamas at the head of the inlet is one of the most sheltered overnights in the western Cyclades and the stop where the crew gets the first relaxed evening. Sarakiniko on the way past is the unmissable swim stop — bone-white volcanic moonscape, but the anchorage is exposed and only viable in calm wind.

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.

Day 3

Milos → Paros (Parikia)

Long 35 nm leg via Sifnos. Lunch swim at Vathi Bay on Sifnos — sheltered and one of the calmest swim anchorages in the western Cyclades — then continue north 18 nm to Parikia on Paros. Parikia is bigger than Naoussa, less photogenic but easier mooring; the harbour is dredged and stern-to is straightforward. The 4th-century Panagia Ekatontapiliani (Church of a Hundred Doors) sits in the centre of the old town.

Things to do

Swim stop at Sifnos Vathi Bay

Visit the 4th-century Ekatontapiliani church

Sunset off Kolymbithres rocks

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; expect to compete for slot.

Day 4

Paros → Paros

Lay-day on Paros — no leg. Use the morning for laundry and provisioning at Parikia, then anchor at Antiparos for the afternoon (sheltered cove on the east side facing the channel). Kolymbithres lunar rocks are 2 nm round the corner from Naoussa for a swim. Bike rental is the standard way to see Lefkes village in the inland highlands; the marble paths there are some of the prettiest in the Cyclades.

Things to do

Anchor lunch at Antiparos east coast

Swim Kolymbithres lunar rocks

Bike to Lefkes marble village

Wine tasting at a Marpissa vineyard

Mooring tip

Free anchoring at Antiparos east coast on sand at 4-7 m. Stern-to in Parikia or Naoussa for the overnight; switch from morning anchor to evening berth.

Day 5

Paros → Syros

24 nm northwest to Syros — beam reach in Meltemi, one of the better sailing legs of the round trip. Ermoupoli town quay sits at the head of a deep harbour and is one of the most forgiving mooring positions in the entire Cyclades. The capital climbs the slope above in pastel neoclassical layers — Greek-orthodox Vrontado on one hill, Catholic Ano Syros on the other, the only Cycladic town where both communities are roughly equal in size.

Things to do

Climb Ano Syros for the Catholic quarter

Loukoumi tasting at a 19th-century confectionery

Walk Miaouli marble square at dusk

Swim the rock platforms at Asteria Beach

Mooring tip

Stern-to on Ermoupoli town quay (no fee, your own anchor). Excellent shelter in any wind direction. Manna marina slot for €60-80/night if quay is full.

Day 6

Syros → Tinos

14 nm hop east-southeast — the breeziest channel in the central Cyclades. Gap effect adds 5 knots to the regional forecast and 25-knot afternoons are normal in late July. Beam reach at speed but plan to be moored before 16:00. Tinos new harbour stern-to has moderate sand holding; the inner small craft harbour is the calmer alternative when Meltemi is forecast above 25 knots. Tinos is the marble-carving capital of the Aegean.

Things to do

Marble-carving workshop visit in Pyrgos

Walk the dovecote trail above Falatados

Artichoke à la polita lunch in a courtyard

Sunset at Volax granite-boulder field

Mooring tip

Stern-to in Tinos new harbour, €25-40/night. Holding moderate sand — set anchor with long scope. Inner craft harbour is calmer above 25 kn.

Day 7

Tinos → Mykonos (Tourlos Marina)

Short 8 nm leg east to Mykonos — Tinos-Mykonos channel reliably 5 knots stronger than the regional forecast, short choppy state in the afternoon. Pre-book a slot at Tourlos New Marina online 24 hours ahead in July-August. The older Mykonos town quay is free but very exposed to swell, only viable if Meltemi is forecast below 18 knots. Day-anchor at Ornos or Psarou for an afternoon swim before mooring.

Things to do

Day-trip across to ancient Delos

Beach lunch at Agios Sostis (no road access)

Walk the Little Venice waterfront at sunset

Hike the Armenistis lighthouse loop

Mooring tip

Stern-to in Tourlos New Marina, €70-110/night peak. Pre-book online for July-August. Mykonos town quay only safe under 18 kn N.

Day 8

Mykonos → Mykonos

Lay-day on Mykonos. The unmissable activity is the day-trip across to ancient Delos — UNESCO archaeological site on the small uninhabited island 3 nm west, sailable as a day-anchor. Marble lions, Apollo sanctuary, mosaic floors, all visible in 3-4 hours ashore. Anchor off the south side in 5-8 m on sand. Otherwise: beach-hop the south coast (Paradise, Super Paradise, Elia, Agrari) and end the day at Scorpios for sunset.

Things to do

Day-anchor at Delos archaeological site

Walk the Apollo sanctuary and lion terrace

Beach lunch at Agios Sostis

Sunset at Scorpios beach club

Mooring tip

Tourlos Marina overnight as the day before. Day-anchor at Delos south side on sand at 5-8 m, no overnight allowed (closes sundown). Return to Tourlos by 19:00.

Day 9

Mykonos → Amorgos (Aegiali Harbor)

Long 35 nm passage southeast to Amorgos. The leg crosses open water away from the headline Cyclades and into the Small Cyclades zone — fewer charter boats, quieter anchorages. Aegiali on the north coast is the safer overnight in N Meltemi (Katapola on the south is the alternative). The cliff-clinging Hozoviotissa Monastery 6 nm south is the headline excursion: 300 steps up the cliff face from the road, brilliant white walls against ochre rock.

Things to do

Climb to cliff-clinging Hozoviotissa monastery

Dive the Olympia shipwreck off Liveros

Psimeni raki and goat in a Tholaria taverna

Hike the Aegiali-Tholaria ridge path

Mooring tip

Aegiali stern-to, €25-40/night, sheltered from N. Katapola is the south-coast alternative for wind from the south. Confirm slot in peak season — Amorgos has limited charter capacity.

Day 10

Amorgos → Irakleia

18 nm west into the Small Cyclades cluster. Irakleia is the smallest of the four populated Small Cyclades islands (Donousa, Schinoussa, Koufonisia and Irakleia) — population 100, one taverna at Agios Georgios harbour, a single road, and the Blue Cave 30 minutes hike from the village. This is where Cyclades cruising goes quiet: the headline tourist crowd never reaches the Small Cyclades.

Things to do

Hike to the Blue Cave (30 min from village)

Beach swim at Livadi (best swim water in the Small Cyclades)

Grilled gouna sun-dried mackerel at the harbour taverna

Walk the kastro pirate-era ruins

Mooring tip

Anchor in Agios Georgios bay on sand at 5-7 m. Sheltered from N Meltemi. Small quay slots for €15-25/night, lazy lines absent.

Day 11

Irakleia → Naxos

20 nm northwest to Naxos — the largest Cycladic island, fertile interior, mountains over 1000 m. Naxos town harbour is well-protected and stern-to is reliable. The Portara — a single marble doorway from the unfinished 6th-century BC Apollo temple — sits on the small islet at the harbour entrance and is the headline sunset spot. Inland, Mount Zas (1004 m) is the Cyclades highest peak and a 4-hour hike from Filoti village.

Things to do

Sunset at the Portara marble doorway

Hike Mount Zas (Zeus birthplace, 4 h)

Kitro citron liqueur tasting at Halki

Swim Agios Prokopios Beach

Mooring tip

Stern-to in Naxos town harbour, €30-50/night. Well-protected from any wind direction. Plenty of slot capacity even in peak season.

Day 12

Naxos → Ios

20 nm south through the Naxos-Sikinos channel — Meltemi reach. Plan a swim stop at Manganari Bay on the south coast of Ios, then back round to Ormos for the overnight. Ios is the late-night party island of the central Cyclades: Chora square fills with crowds from 23:00, and the small alleys turn into open-air clubs through the summer months.

Things to do

Swim stop at Manganari Beach

Hike to the supposed tomb of Homer above Plakotos

Chora rembetika square late-night

Sunset drinks above the windmills

Mooring tip

Ormos harbour stern-to, €25-40/night. Mylopotas anchorage is daytime only — untenable overnight in Meltemi. Manganari is sheltered from N for swim stop.

Day 13

Ios → Santorini (Vlychada Marina)

Last leg back to Santorini — 18 nm south. Plan a swim stop at Thirasia (the small inhabited island on the west side of the caldera) before rounding the south coast to Vlychada Marina. The caldera entry is dramatic but anchoring is impossible (300+ m); the cruise-ship buoys off Thirasia are not reliable for charter. End the trip with a taxi to Oia for the cliff-top sunset before the morning handover.

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.

Day 14

Santorini → Check-out

Handover at Vlychada before 09:00. Boat inspection with the skipper present — deposit released within 7 days. Crew transfer to Santorini airport (JTR) is 25 minutes by road. Last morning swim at Ammoudi Bay below Oia (taxi from Vlychada) and breakfast at a caldera-edge café is the standard last-day routine.

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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Santorini via Mykonos & Milos.

Day-by-day route

Santorini (Vlychada Marina) → Folegandros

Route at a glance

Route summary