Athens - Mykonos - Santorini - Paros
Day 1
Athens - Kea (Vourkari)
Day 2
Kea - Syros (Ermoupolis)
Day 3
Syros - Tinos
Day 4
Tinos - Mykonos
Day 5
Mykanos - Paros (Naousa)
Day 6
Paros - Ios
Day 7
Ios - Santorini
Day 8
Santorini - Folegandros
Day 9
Folegandros - Milos (Adhamas)
Day 10
Milos - Sifnos (Kamares)
Day 11
Sifnos - Serifos
Day 12
Serifos - Kithnos (Merihas)
Day 13
Kithnos - Athens
Day 14
Checkout
Detailed Itinerary by days
Day 1Athens - Kea (Vourkari)
Starting your journey in Athens, where the Acropolis guards over a city humming with espresso-fueled activity, Go northeast; the Aegean stretches ahead like a sapphire promise. Anchor at Kea's Vourkari Bay—a crescent of blue edged with tamarisk trees. Explore the WWII wreck Brittany at twilight, then feast on octopus carpaccio at a riverfront bar; the harbor lights flickering like fireflies
Day 2Kea - Syros (Ermoupolis)
Let the Meltemi winds guide you into Syros, where neoclassical homes slink down Ermoupolis's hill sides like a pastel waterfall. Wander marble-paved lanes to Miaouli Square, where great cafes buzz with rumors. Climb the labyrinthine stairs of Ano Syros at sunset while bouzouki music floats from blue-door bars. Not missed is a slice of century-old confectionary loukoumi, or rosewater Turkish pleasure.
Day 3Syros - Tinos
Sail to Tinos, the heart of the Cyclades spiritually. Dock under the famous Church of Panagia Evangelistria, its pilgrims on knees. Escape to Volax village, where the terrain is sculpted like old monuments by massive granite rocks. Lunch on artichokes a la polita in a farm-to-- table courtyard; then, search Pyrgos for marble crafts—the mysteries of the island carved in stone.
Day 4Tinos - Mykonos
Trade peace for sizzle as the windmills of Mykonos rise on the horizon. Beach-hop from the DJ rhythms of Paradise to Agios Sostis' secret peace. Get lost in the maze of designer boutiques and blue-domed chapels that is Mykonos Town. Dine on lobster pasta in Little Venice, the waters lapping at your feet, then dance until morning under a sky peppered with stars.
Day 5Mykanos - Paros (Naousa)
Sail to Paros' Naousa, a postcard-perfect fishing harbor where boats sparkle next worn-out kaikia and octopuses dry on ropes. swim on the moon-rock beaches of Kolymbithres, then sip Assyrtiko wine from a vineyard built on old marble quarries. Join the vibe at a seaside cocktail bar as evening falls—the air heavy with jasmine and music.
Day 6Paros - Ios
Allow the waves to bring you to Ios, where all-night celebration meets beautiful beaches. Claim a sunbed in Mylopotas, then climb to Homer's legendary tomb for breath-stealing sunset vues. By midnight the hamlet square bursts in rembeka music and clinking ouzo glasses. Pro tip: All sins are healed at Magganari Beach by morning dips.
Day 7Ios - Santorini
Get to Santorini in afternoon light, the calera ablaze. Swim in volcanic hot springs from Thirasia, the gentler twin of the volcano. After sailing to Oia for the sunset—the sky melting into colors of apricot and rose—then savor fava with capers in a cliffside cave restaurant. Night sleep? Overly praised.
Day 8Santorini - Folegandros
Leave the throngs behind and find Chora's whitewashed village clinging to cliffs like a seabird's nest in Folegandros. Trekking the zigzag road to Panagia church, the Aegean stretches out like a blue silk sheet. Dinner is here. In a courtyard illuminated by lanterns, matsata (hand-cut pasta) with wild goat ragù. Perfection does not call for neon.
Day 9Folegandros - Milos (Adhamas)
Milos shows up, a rainbow of volcanic colors. Then sail into Klima's candy-colored syrmata (fishermen's homes), kayak Sarakiniko's bone-white moonscape. Explore the sea caves of Papafragas and celebrate the day on a boat deck with a sunset cocktail reflecting Adhamas's crystal harbor.
Day 10Milos - Sifnos (Kamares)
Chart Sifnos, the gastronomic master of the Cyclades. At Kamares, where cerulean waves kiss a golden arc of sand, dock. Trek to the thin rock cleft by the sea, the Chrysopigi monastery, then feast on mastelo—lamb roasted in clay pots—at a hillside taverna. Secret: The croquettes made from chickpeas here destroy everything else.
Day 11Sifnos - Serifos
The untamed beauty of Serifos emerges—a jagged form against the horizon. Anchor in Livadi's horseshoe bay, then climb the donkey path to Chora, a white cube house swarm. Lunch at a cliffside kafeneio on revithada, lemony chickpea stew, with a cat dozing at your feet. Greece stripped naked, raw and brilliant is what this is.
Day 12Serifos - Kithnos (Merihas)
Ship to Kithnos, where simplicity rules. Swim in the sliver of sand separating twin bays at Kolona Beach or relax in Loutra's hot springs, heated by the pulse of the earth. At a harbour taverna, dine on grilled sfoungato (cheese pie), the stars so near you will swear you could grab them from the heavens.
Day 13Kithnos - Athens
Allow the Saronic Gulf to lead you home; dolphins chasing your bow as Athens' skyline rises. Stop for one last swim at the temple of Poseidon at Cape Sounion. Return to Piraeus and celebrate your journey with ouzo and spicy taramasalata, the Acropolis glittering golden far away. "Next year," the sea murmurs.
Day 14Checkout
Set sail with the wind in your hair, a memory card full with sunsets, and a soul burdened by the enchantment of the Aegean. While enjoying a breakfast of honey-drenched yogurt, you can't help but fantasize about going back to these islands. Not flings, but lovers.