Santorini
via Mykonos & Milos.
Catamaran charter Greece — 14-day Santorini, Mykonos & Milos Cyclades route. Volcanic islands, classic Mykonos & Delos, two-week loop.
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) → Folegandros
Cast off from Vlychada and run 14 nm WNW to Folegandros — easy beam reach in normal Meltemi. Pocket harbour at Karavostasi; dramatic cliffside chora reachable by 4 km zigzag road.
Distance
30 NM
Sailing
~6h at 5 kn
Route at a glance
Best season
May – October
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.
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) → Folegandros
Sail to the untamed beauty of Folegandros and forget about the volcanic drama of Santorini. Set sail for the hidden nook of Katergo Beach, where the pristine waters and pebble beach await. Eat matsata (hand-cut pasta) with wild goat ragù under strings of lamps after hiking the cliffside walk to Chora, a settlement that clings to the rocks like a seabird's nest.
Things to do
Anchor & swim at Katergo Beach
Climb the cliff walk to Chora
Dinner of matsata pasta in Chora
Sundowner at a cliff-edge bar
Coastal hike to Agali bay
Mooring tip
Stern-to in Karavostasi (lazy lines on the new mole, small fee) or anchor in the bay (5–8 m sand). Open to S — re-anchor or move in S–SW switch.
Folegandros → Milos (Adamantas Port)
Twenty-two nautical miles west-northwest from Folegandros onto Milos — ducking into the deep inner lagoon at Adamantas, the best Meltemi shelter in the western Cyclades. Adamantas sits inside a flooded volcanic caldera, one of the largest natural harbours in the Mediterranean — almost zero swell inside no matter what the wind does outside. Stern-to on the town quay (free, helpful local boatmen will take the lines) or anchor inside the inner bay at 4–6 m on soft mud — set the anchor well, the bottom is loose under the weight. Milos is volcanic and the colour palette around the coast is the headline: Sarakiniko on the north coast is the moonscape walk, white volcanic rock eroded into ridges and pools (day-stop only — the anchorage there is open to the N); Klima on the west has the rainbow syrmata row, fishermen's boat-house garages from the 19th century painted in solid primary colours. Snorkel through Papafragas sea caves on the east coast. Grilled octopus dinner at Mandrakia, the working fishing village 4 km north. Sundowner from Plaka village ridge.
Things to do
Sarakiniko white-rock anchor & swim
Snorkel Papafragas sea caves
Photograph Klima syrmata at golden hour
Grilled octopus dinner at Mandrakia
Sundowner from Plaka village ridge
Mooring tip
Stern-to on Adamantas town quay (free, helpful local boatmen) or anchor inside the inner bay (4–6 m, soft mud — set well). Sarakiniko anchorage open to N — day-stop only.
Milos → Paros (Parikia Harbor)
Early morning: sail to Sifnos's Kamares, then hike to the arched seafront Chrysopigi Monastery. Lunch at Artemonas on mastelo, or clay-pot lamb. Glide to Paros' Parikia afternoon, where the fourth-century Panagia Ekatontapiliani church guards whitewashed alleyways. Swimming in Kolymbithres' lunar rocks at sunset will cap the day.
Things to do
Hike Chrysopigi monastery cape
Lunch on mastelo at Artemonas
Visit Panagia Ekatontapiliani 4th-c. church
Swim Kolymbithres rock pools
Sundowner at Parikia waterfront
Mooring tip
Stern-to on Parikia main quay (free, busy with ferries — keep clear) or alongside the south mole. Anchor option: Krios bay just N of port (sand 5–8 m). Bypass Sifnos overnight.
Paros → Paros
Day off the helm on Paros — stay berthed at Parikia or short hop 8 nm round to Naoussa for a change of scene. The Naoussa small Venetian-fortress fishing harbour fills early; anchor in the bay at 5–7 m sand if the quay is full, with Krios bay just north of Parikia as the quiet alternative. Inland, Lefkes mountain village sits at 300 m on the central spine of the island — jasmine-scented alleys around the marble agora, a 17th-century Cretan-Venetian foundation, the easy 5 km Byzantine Road downhill walk to Prodromos for the afternoon. Marpissa winery on the east coast runs Assyrtiko tastings on the volcanic-soil vineyards (book ahead — small operation, family-run). Golden Beach further south is the Cycladic windsurfing championship venue; the Meltemi delivers a reliable 25-30 kn cross-shore most July afternoons. Octopus souvlaki on the Naoussa quay for dinner, then back to base for laundry and provisioning before the next leg.
Things to do
Bike to Lefkes's jasmine alleys
Stroll Naoussa's old fishing harbour
Lunch on octopus souvlaki
Windy beach session at Golden Beach
Marpissa winery Assyrtiko tasting
Mooring tip
Stay overnight in Parikia or motor up to Naoussa (8 nm). Naoussa small harbour fills early — anchor in the bay (5–7 m sand) if quay is full. Krios bay is the quiet alternative.
Paros → Syros
The neoclassical city of Ermoupoli on Syros is a sight to behold, with its pastel houses and marble streets. While perusing the rosewater loukoumi at a shop that dates back 150 years, ascend Ano Syros to take in the sunset views. Final drink: Ouzo at a seedy rembetiko establishment.
Things to do
Wander marble-paved Ermoupoli waterfront
Climb Ano Syros for sunset over Tinos
Buy rosewater loukoumi at the old confectionary
Lunch at Vaporia neighbourhood seafront
Late ouzo in a rembetiko taverna
Mooring tip
Stern-to on Ermoupoli main quay (free, plenty of length, secure even in 30 kn Meltemi). True weather refuge of the Cyclades. Foulkrod side keep clear of ferries.
Syros → Tinos
Twelve nautical miles east onto Tinos — short hop on a comfortable beam reach, but the channel between Syros and Tinos can funnel the Meltemi to 30 kn and above; reef the main early. Tinos main port can be choppy in fresh Meltemi — use the inner mole or pull across to the Mykonos lee if the forecast looks gnarly. Stern-to inside the harbour (lazy lines, ferries close — keep clear of their working berth); Panormos on the north coast is the alternative anchorage on 5–8 m sand. Tinos is the pilgrim island of Greek Orthodoxy — the icon of the Annunciation at Panagia Evangelistria above the port draws 500,000 pilgrims every August 15, many crawling the carpet up from the quay on their knees. Pyrgos in the marble interior is the sculpture village — Greek sculptors have been trained there for 300 years and a working studio is open to visitors. Lunch on artichokes à la polita in a Tinos courtyard. Kolymbithra Beach on the north coast is the surf school and afternoon swim; Exomvourgo crusader ruins on the central peak is the inland walk if the legs allow.
Things to do
Visit Panagia Evangelistria pilgrim church
Drive up to Pyrgos marble-sculptor village
Lunch on artichokes à la polita
Explore Exomvourgo crusader ruins
Surf Kolymbithra windswept waves
Mooring tip
Stern-to inside Tinos main port (lazy lines, ferries close — keep clear). Open to N gusts. Anchor option: Panormos on the north coast (sand 5–8 m).
Tinos → Mykonos (Tourlos Marina)
Eight nautical miles southeast onto Mykonos — short comfortable hop, often spinnaker-friendly in the standard Meltemi N flow. Tourlos New Marina 2 km north of Mykonos Old Port is the only safe overnight option; book a berth weeks ahead for July or August arrivals (lazy lines, full marina services, fee). The old port still works for ferries but is exposed to the N Meltemi and is not viable for charter overnight. There is no safe anchorage on Mykonos in N winds — the entire island sits in the wind shadow of nothing. Mykonos Town below the famous Kato Mili windmills earns its loud reputation: Little Venice (the row of 16th-century houses with balconies built directly onto the rocks at the waterline) for sundowner cocktails before the night kicks off; Paradise and Super Paradise for the day-club beach scene; Agios Sostis on the north coast for the quiet swim if the day-club thump is not what the crew wants. Lobster spaghetti at any Little Venice taverna for dinner. Late dance under the windmills.
Things to do
Beach-hop Paradise & Super Paradise
Sundowner cocktail at Little Venice
Photograph the windmills at twilight
Day-trip ferry to Delos archaeological site
Dinner of lobster spaghetti in Chora
Mooring tip
Tourlos (New Marina) only — book weeks ahead in season, lazy lines, full marina services, fee. Old port exposed to Meltemi. No safe anchorage on Mykonos in N winds.
Mykonos → Mykonos
I am free to enjoy today! Discover the old remains of Delos, peruse the lanes of Mykonos Town for linens, and relax on Super Paradise Beach. At Scorpios, you must have a sunset cocktail while you watch the Aegean turn golden.
Things to do
Day-trip ferry to Delos archaeological site
Linen-shop Mykonos Town's lanes
Beach lounge at Super Paradise
Sundowner cocktail at Scorpios
Late dinner in Little Venice
Mooring tip
Stay overnight in Tourlos (already booked). Old port still no-go in Meltemi. Restock at the marina supermarket — limited fresh produce options on the south beaches.
Mykonos → Amorgos (Aegiali Harbor)
Thirty-eight nautical miles southeast from Mykonos onto Amorgos — long day at sea, beam-to-broad reach in the classic Meltemi N flow, sometimes spinnaker-friendly when the wind clocks NW. Cast off by 07:00 to clear the open water before the afternoon breeze hardens above 25 kn. Aegiali on the north coast is the morning destination; the bay opens to the NE, so if the forecast tops 25 kn, shift round to Katapola on the south coast for the better lee. Stern-to on the small Aegiali quay (lazy lines, fee, 12 boats) or anchor in 5–8 m sand off the village. The headline ashore is the Hozoviotissa Monastery — the white cliffside chapel built directly into the limestone face above Agia Anna in 1088, reached by 300 marble steps from the road, the most photographed building in the Cyclades after the Oia caldera. Dive the Olympia wreck off the south coast in the shallow water — the 1980 cargo ship that the 1988 Luc Besson film The Big Blue used as the underwater set is still there at 25 m. Late raki at a harbour kafeneio on psimeni raki — honey-spiced spirit, the Amorgos local.
Things to do
Hike up to Hozoviotissa Monastery
Dive the Olympia wreck shallows
Stroll Aegiali whitewashed lanes
Late raki at a harbour kafeneio
Walk the southern coast path
Mooring tip
Aegiali Bay anchor in 5–8 m sand or stern-to on the small quay (lazy lines, fee). Open to NE — Katapola on the south coast is the better Meltemi alternative.
Amorgos → Irakleia
Twenty nautical miles west-southwest from Amorgos onto Irakleia — last and least-developed of the Small Cyclades, fewer than 150 year-round residents, one village (Panagia) up the hill, a single ferry per week from Naxos. There is no real marina; anchor in Agios Georgios Bay (the harbour cove on the north coast, 4–6 m sand, holding good) or in the smaller Livadi cove on the south, with the tiny inner quay taking only 1–2 boats. Open to the N — pick a south-facing bay if a fresh Meltemi is forecast. The headline ashore is the Kastro hilltop ruins above Panagia village — a 17th-century Venetian-era pirate refuge built on a Hellenistic foundation, reached by a 40-minute walk through the olive groves from the harbour. The Blue Cave on the south coast is the snorkel ride, a sea-cleft chamber that lights up at noon. Lunch at a beach shack on grilled gouna — sun-dried mackerel, the small-island preservation method that turns the catch into chewy fish-jerky cut into strips. Sunset walk on the western cape closes the day.
Things to do
Snorkel the Blue Cave entrance
Hike to Kastro hilltop ruins
Lunch grilled gouna at a beach shack
Swim Livadi long sand beach
Sunset walk on the western cape
Mooring tip
Anchor in Agios Georgios bay (sand 4–6 m) or the small Livadi cove. Tiny inner quay only takes 1–2 boats. Open to N — pick a south-facing bay in fresh Meltemi.
Irakleia → Naxos
Fourteen nautical miles north-west from Irakleia onto Naxos — comfortable beam reach, often spinnaker-friendly when the wind clocks west of north. Naxos opens up at the marble Portara on the harbour entrance, the surviving lintel of an unfinished 6th-century BC Apollo temple that was abandoned when Samos took the local stone-quarrying contract. The marble frame catches the sunset on every west-facing approach. Naxos Marina south of town is the largest in the central Cyclades — lazy lines, fees, water and power, marina office on VHF 09 — and books out hard in July and August; reserve weeks ahead. The town quay is the second option but gets tight for catamarans. Drive inland to Apiranthos, the marble-streeted highland village settled by Cretans who fled Ottoman raids in the 17th century, then up Mount Zas (the highest peak in the Cyclades at 1004 m, the cave near the summit was the Bronze Age cult site of Zeus's birthplace). Kitro-glazed pork at any mountain taverna; sundown swim at Agios Prokopios south of town.
Things to do
Photograph Portara at sunset
Hike Mount Zas summit trail
Lunch on kitro-glazed pork
Swim Agios Prokopios long sand
Wander old chora marble streets
Mooring tip
Naxos Marina (south of town) — lazy lines, fees, water/power available, busy in season. Reserve in advance. Town quay also possible but tight for catamarans.
Naxos → Ios
Sixteen nautical miles south from Naxos onto Ios — easy beam reach, often spinnaker-friendly in the standard Meltemi N flow. The town quay below the Chora is the headline berth (free, fills early in summer); if it tops out by mid-afternoon, anchor in Manganari Bay on the south coast (5–8 m sand, well sheltered from the prevailing N) and tender into town for the evening. Manganari is also the day-anchor swim — a wide sandy crescent backed by low pumice cliffs that the south-east lee keeps calm. Above the port, the whitewashed Chora climbs the cliffs in a tight maze of stairs and white-cubic houses; the Homer's Tomb walk on the northern cape is a 25-minute climb (Ios tradition holds the poet was buried here on his way back from Samos), and the broken-marble grave gives the photogenic sundown view back across the Aegean. Snorkel Mylopotas Beach turquoise shallows in the morning. Late dinner in the back lanes — Ios runs the loudest summer nightlife in the Cyclades after Mykonos, with ouzo shots and rembetika in the alleys until 03:00.
Things to do
Anchor & swim at Manganari Bay
Climb to Homer's Tomb for sunset
Walk Chora's whitewashed alleys after dark
Snorkel Mylopotas turquoise shallows
Late-night cocktail in Ios old town
Mooring tip
Stern-to on Ios town quay (free, fills early in summer) or anchor in Manganari Bay (south coast, 5–8 m sand, well-sheltered from Meltemi). Town port exposed to N gusts.
Ios → Santorini (Vlychada Marina)
Eighteen nautical miles southeast from Ios back onto Santorini — Vlychada Marina on the south coast is the only viable sailing-yacht overnight on the island. The famous caldera looks dramatic on the chart but is too deep to anchor (300+ m water, sheer volcanic walls); always book Vlychada days ahead in summer (small marina, lazy lines, fee, full services on the quay). Ferry boats between Athinios port and the islands move through the marina entrance fast — plan arrival before dark, the entrance is narrow and unlit. The headline above water is the caldera itself — a 12 by 7 km flooded volcanic crater that took its current shape in the 1646 BC Minoan eruption that buried the Bronze Age city of Akrotiri (the Pompeii-style site is a 10-minute drive from Vlychada and worth the half-day). Kayak the rust-coloured Red Beach cliffs at the south coast for the morning. Sundown fava and capers at any Oia caldera-edge taverna; sundown over the white-and-blue domes for the cliché last-night photograph the trip earns.
Things to do
Kayak the Red Beach rust-hued cliffs
Sundowner at an Oia caldera-edge taverna
Akrotiri Bronze-Age site visit
Fava with capers at a quay taverna
Walk Fira-to-Oia caldera trail
Mooring tip
Vlychada Marina (south coast) — small, lazy lines, fee, full services. Book days ahead in summer. NO caldera anchorage. Plan arrival before dark — entrance is narrow.
Santorini → Santorini
Final morning at the Santorini Vlychada base — the technical hand-back is straightforward when fuel was sorted at the Friday 18:00 briefing. Boat back by 09:00 Saturday for the marineros' inspection, papers signed at reception. Vlychada has fuel and water at the inner mole. If the morning frees up before the airport transfer, the run up to Ammoudi Bay below Oia is the last swim — a small horseshoe of black volcanic sand and pebble at the foot of the 200-step caldera-edge stairs, where a row of seafront tavernas serves the catch from the morning fishing boat. Breakfast at a cliffside Fira café on Greek coffee and spanakopita with the caldera 300 m below. Santorini JTR airport is a 25-minute taxi from Vlychada; book the transfer the evening before in August peak. Pick up volcanic-rock soap and a bottle of Vinsanto sweet wine on the way out — the post-fermentation Vinsanto from the local Assyrtiko grape is the indigenous dessert wine. Disembark with sea-stiff hair and the long memory of a black-cliff sundown.
Things to do
Last dip at Ammoudi Bay
Breakfast spanakopita at a cliff café
Pack and sweep cabins
Refuel before hand-back
Technical hand-over with company
Mooring tip
Return to Vlychada by 17:00 the day before for the agreed hand-back; sleep aboard the final night, disembark by 09:00. Vlychada has fuel & water at the inner mole.
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