Paros - Siros - Milos - Ios (14 days)
Day 1
Paros - Sifnos (Kamares Harbor)
Day 2
Sifnos - Serifos (Livadi)
Day 3
Serifos - Kythnos (Loutra)
Day 4
Kythnos - Syros
Day 5
Syros - Mykonos (Tourlos Marina)
Day 6
Mykonos - Naxos
Day 7
Naxos - Ios
Day 8
Ios - Santorini (Vlychada Marina)
Day 9
Santorini - Santorini
Day 10
Santorini - Folegandros
Day 11
Folegandros - Milos (Port Adamantas)
Day 12
Milos - Sifnos (Vathi Port)
Day 13
Sifnos - Paros
Day 14
Paros - Check-out
Detailed Itinerary by days
Day 1Paros - 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.
Day 2Sifnos - 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.
Day 3Serifos - 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.
Day 4Kythnos - 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.
Day 5Syros - 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.
Day 6Mykonos - Naxos
Under the famous marble gateway to Apollo's temple, Portara, sail to Naxos. Visit Apiranthos, a highland town with marble-paved streets, then have pig (citrus liquor from nearby lemons) kitro-glazed. Finish the day at Agios Prokopios swimming under the moon.
Day 7Naxos - Ios
Track the horizon toward Ios, where golden dunes meet all-night celebration. From the turquoise coves of Snorkel Manganari Beach, climb to Homer's Tomb for sunset panoramas, then plunge into Chora's electric alleys—ouzo shots, rembetika sounds, starlit anarchy.
Day 8Ios - Santorini (Vlychada Marina)
From Vlychada, a lunar marina with black-sand beaches, arrive at Santorini. After kayaking the rust-hued cliffs of Red Beach, have sunset fava with capers at a caldera-edge restaurant. The white domes of Oia sparkle like dusk pearls.
Day 9Santorini - Santorini
Free day to explore! Discover the Bronze Age remnants of Akrotiri, sail the volcanic caldera, or sip Assyrtiko in a vineyard along a cliff. Finish on Ammoudi Bay, where flaming heavens meet azure waves.
Day 10Santorini - 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.
Day 11Folegandros - 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.
Day 12Milos - 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.
Day 13Sifnos - Paros
Returning to Paros, explore Naoussa's elegant waterfront for octopus souvlaki and people-watching. Final swim in the moon rock pools of Kolymbithres, then a goodbye feast of xinomavro wine and seafood saganaki.
Day 14Paros - Check-out
Greek coffee in Parikia's lanes and last breakfast of koulouri, sesame bread. Disembark with whispered vows: "Till next time, Aegean," a camera roll of Cycladic enchantment, and salt-streaked hair.
