Paros
via Siros & Milos.
Catamaran charter Greece — 14-day Mykonos, Syros, Milos & Ios route. Volcanic Sarakiniko, Ios old town, Sifnos & Folegandros across two weeks.
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.
Paros → Sifnos (Kamares Harbor)
Cast off from Paros and angle southwest with a beam reach to Sifnos — about 28 nm to Kamares Bay, sheltered from the prevailing N–NE Meltemi behind a steep granite headland. Easy first leg, arrive by lunch.
Distance
22 NM
Sailing
~4.4h at 5 kn
Route at a glance
Best season
May – October
Duration
14 days · Sat – Sat
Departure
Paros
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.
Paros → Sifnos (Kamares Harbor)
Start your trip in Paros and sail southwest to Sifnos' Kamares Harbor, which has a golden arc of sand set by blue waves. Take a walk to the Chrysopigi Monastery and see how the stone arches there resist the pull of the sea. In Artemonas village, eat mastelo, which is clay-pot lamb with red wine. Tip for sailors: Set your anchor early, because this bay gets full by noon.
Things to do
Hike the path to Chrysopigi Monastery
Lunch on mastelo at Artemonas village
Pottery-studio visit (Sifnos clay tradition)
Snorkel the rocky shore north of Kamares
Sunset stroll along Apollonia ridge
Mooring tip
Anchor west side of Kamares Bay (5–8 m sand, decent holding) or stern-to on the small ferry quay if free. Bay fills by noon in August — drop hook early. Open to W swell when wind backs.
Sifnos → Serifos (Livadi)
It's better to trade Sifnos' polish for Serifos' rough Cycladic beauty. Land your boat in Livadi, a crescent of golden sand, and walk along the zigzag path to Chora, a cluster of pale cube houses that clings to a volcanic peak. At a taverna on a cliff, we ate lunch of revithada (lemon chickpea stew) while looking out over the Aegean Sea.
Things to do
Zigzag walk up to Chora
Lunch revithada at a cliffside taverna
Swim Livadakia & Karavi beaches
Visit the abandoned Serifos iron mines
Sundowner on the chora ridge
Mooring tip
Stern-to on Livadi town quay (free, lazy lines on inner side) or anchor in 5–6 m sand off the beach. Bay open to E swell — fine in normal Meltemi N flow.
Serifos → Kythnos (Loutra)
Sail to the Loutra of Kythnos, where hot springs bubble like a spa in nature. Then swim Kolona Beach, a sliver of beach separating twin turquoise bays, in mineral-rich waters formerly treasured by Byzantine emperors. Meals? Under a sky studded with stars, grilled sfougato, or cheese pie, tastes great.
Things to do
Soak in the Loutra thermal springs
Anchor & swim at Kolona double-bay
Walk up to Chora & Driopida villages
Try sfougato (cheese pie) for dinner
Sunset paddle from the boat to Apokrousi
Mooring tip
Stern-to on Loutra quay (small marina on NE coast, lazy lines, fee). Best Meltemi shelter on Kythnos. Kolona bay anchor only in light winds — exposed to N.
Kythnos → Syros
Glide into Syros' Ermoupoli, a neoclassical jewel with marble-paved streets and pastel homes. Climb Ano Syros at nightfall, bouzouki music wafting from blue-door tavernas, and munch rosewater loukoumi from a 19th-century confectionary. Nightcap: Ouzo in a bar serving gritty rembetiko.
Things to do
Wander marble-paved Ermoupoli waterfront
Climb Ano Syros for sunset over Tinos
Buy rosewater loukoumi in 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). Foulkrod side good for ferries — keep clear. True weather refuge of the Cyclades.
Syros → Mykonos (Tourlos Marina)
Dock in the elegant Tourlos Marina of Mykonos, where fishing boats and superyachts take front stage. From the DJ sounds of Paradise, beach-hop from Agios Sostis's hidden peace Eat lobster pasta in Little Venice, then dance until morning under the direction of wind mills. Pro tip: Book marina spaces several weeks ahead.
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 → Naxos
Twenty-two nautical miles southeast under spinnaker if the Meltemi is steady — a tradewind reach in 18–22 kn from the N that asks for the gennaker on the second half of the leg. 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 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 — the marble streets are still cleaned with seawater on Sunday mornings. Kitro-glazed pork at any mountain taverna; sundown swim at Agios Prokopios south of town.
Things to do
Photograph the Portara temple gate at sunset
Drive up to Apiranthos marble-street village
Taste kitro-glazed pork in a highland taverna
Swim Agios Prokopios long sand beach
Hike Mount Zas (highest peak in Cyclades)
Mooring tip
Naxos Marina (south of town) — lazy lines, fees, water/power available, very busy in season. Reserve in advance. Town quay also possible but tight for catamarans.
Naxos → Ios
Sixteen nautical miles south onto Ios — easy beam reach in the steady Meltemi, often spinnaker-friendly when the wind clocks NW. 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; 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 panorama back across the Aegean from the broken-marble grave is the photogenic sundown stop. 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)
Sixteen nautical miles southeast 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 or weeks 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 — keep clear of the dredged channel on approach. 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; vineyard tasting of the volcanic-soil Assyrtiko white in Pyrgos.
Things to do
Kayak the Red Beach rust-hued cliffs
Sunset taverna on the caldera edge in Oia
Tour Akrotiri Bronze-Age archaeological site
Vineyard tasting of crisp Assyrtiko
Walk Fira-to-Oia caldera trail
Mooring tip
Vlychada Marina (south coast) — small, lazy lines, fee, full services. Book days/weeks ahead in summer. NO caldera anchorage (too deep). Ferry boat moves fast — keep clear.
Santorini → Santorini
Free day on Santorini — stay berthed at Vlychada (second night already paid) and the day is a rest off the helm. The volcanic caldera looks like an obvious day-sail, but the gusts that funnel between Thira and Therasia are vicious and unpredictable; only attempt the loop in confirmed light-wind forecast (under 12 kn) and stay in the lee of the southern crater wall. Better day-options ashore: Akrotiri Bronze Age archaeological site (the Minoan town buried by the 1646 BC eruption, preserved under 60 m of pumice ash, opened to visitors in 2012 after a 7-year roof-rebuild) is the morning headline, with the Museum of Prehistoric Thira at Fira holding the recovered frescoes. Vineyard lunch in Pyrgos with Assyrtiko tasting — the kouloura basket-vines are trained as low spiral hoops to protect grapes from the Meltemi. Black-sand swim at Perissa Beach for the afternoon. Sundowner above Ammoudi Bay below Oia for the postcard glow.
Things to do
Akrotiri Bronze-Age archaeological tour
Vineyard lunch with Assyrtiko tasting
Sundowner above Ammoudi Bay
Caldera day-sail (light winds only)
Black-sand swim at Perissa Beach
Mooring tip
Stay overnight in Vlychada — second night already paid is the easiest plan. Avoid moving north into the caldera unless light wind forecast; gusts off the volcano are vicious.
Santorini → Folegandros
See the wild beauty of Folegandros. Swim in the pebbled privacy of Katergo Beach, then climb the cliff path to Panagia Church, the Aegean expanse below. Feast on matsata, hand-cut pasta, in a courtyard lighted by lanterns with wild goat ragù.
Things to do
Climb the path to Panagia Church
Swim & snorkel at Katergo Beach
Dinner of matsata pasta in Chora
Coastal hike along the eastern cliffs
Sundowner at a Chora cliff-edge bar
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 leave if S–SW switch forecast.
Folegandros → Milos (Port Adamantas)
Milos is mesmerized by the snow-white coves of Sarakiniko and the colorful syrmata of Klima. Explore the sea caves of Papafragas and then eat grilled octopus in the fishing huts of Mandrakia. Sunset? As Plaka's town turns gold, raise a glass and toast.
Things to do
Sarakiniko white-rock anchor & swim
Snorkel through Papafragas sea caves
Photograph syrmata fishing houses at Klima
Grilled octopus dinner in Mandrakia
Sundowner at 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 anchor well). Sarakiniko anchorage open to N — day-stop only.
Milos → Sifnos (Vathi Port)
Go back to Sifnos and stop in Vathi's bay that looks like a fjord. You can kayak to Chrysopigi's abbey that is split in two by the sea and then eat chickpea fritters at a tavern by the water. A local secret is that the bay is as quiet as the sky is at dawn.
Things to do
Kayak to Chrysopigi sea-cleft monastery
Long sandy swim across the inner bay
Lunch revithada at a beach taverna
Walk inland to the potters of Apollonia
Sunset paddle to the small cape
Mooring tip
Drop hook in Vathi (5–8 m sand, very good holding) or alongside the small inner quay (limited space). Best Meltemi shelter on Sifnos. Watch the chartered cats raft up after 17:00.
Sifnos → Paros
Twenty-eight nautical miles east-northeast back to Paros — comfortable beam reach with the Meltemi on the port quarter, the textbook end-of-week passage. Plan an early start (07:00 cast-off) to clear the harbour before the breeze hardens above 25 kn in the early afternoon. Naoussa small fishing harbour on the north coast is the headline arrival — the small inner port fills early in season; stern-to on the outer mole or anchor in the bay at 5–7 m sand. Parikia main port on the west coast is the alternative if Naoussa is full or the wind is hard from the N. Kolymbithres on the way into Naoussa is the morning swim — granite rock pools eroded into surreal lunar bowls between the headlands. Walk the old Naoussa fishing harbour at sundown — the cluster of seafood tavernas around the small Venetian fortress runs octopus souvlaki and seafood saganaki as the local plates. Final farewell ouzo on the quay with a side of crisp Paros-island Monemvasia white.
Things to do
Last swim at Kolymbithres rock pools
Stroll Naoussa's old fishing harbour
Goodbye seafood saganaki on the quay
Photograph the Antiparos sound at sunset
Parikia ouzo & old-town lanes
Mooring tip
Naoussa small harbour fills early — stern-to on the outer mole or anchor in the bay (5–7 m sand). Parikia main port is the alternative if Naoussa is full or wind is hard from N.
Paros → Paros
Final morning at the Paros 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. Parikia harbour has full fuel and water at the south mole; the on-quay marina shop handles the technical exit checklist (bottom reading, electronics test, gear inventory). Walk Parikia old town one last time — the Panagia Ekatontapiliani Byzantine basilica two blocks inland is one of the oldest standing churches in Greece, founded in the 4th century and rebuilt under Justinian; the marble baptismal font is the original 5th-century basin. Ferries to Athens (Piraeus) run hourly through the day — the high-speed Seajet does the trip in 3 hours, the conventional ferry in 5. Paros JTR airport for direct flights to Athens (35 min) is a 10-minute taxi from the harbour. Disembark with sea-stiff hair and the long memory of a Meltemi day on the beam.
Things to do
Final breakfast of koulouri & coffee
Pack and sweep cabins
Refuel at base before hand-back
Technical hand-over with charter company
Walk Parikia old town one last time
Mooring tip
Return to base by 17:00 the day before for the agreed hand-back; sleep aboard the final night, disembark by 09:00. Parikia harbour has full fuel & water at the south mole.
Sail this route — we'll match a catamaran to it.
Send dates, group size and preferred catamaran style. A broker replies with a tailored quote within hours.