Paros - Milos - Santorini - Syros (14 days)
Day 1
Paros - Naxos
Day 2
Naxos - Donoussa
Day 3
Donoussa - Amorgos (Aegiali Harbor)
Day 4
Amorgos - Koufonissi
Day 5
Koufonissi - Schoinousa
Day 6
Schoinousa - Irakleia
Day 7
Irakleia - Santorini (Vlychada Marina)
Day 8
Santorini - Folegandros
Day 9
Folegandros - Milos
Day 10
Milos - Sifnos
Day 11
Sifnos - Serifos
Day 12
Serifos - Kythnos
Day 13
Kythnos - Paros
Day 14
Paros - Check-out
Detailed Itinerary by days
Day 1Paros - Naxos
Starting in Paros and sailing to Naxos under the wary eye of the Portara, a marble doorway to Apollo's old temple, After eating kitro-glazed pork in a rural taverna, hike Mount Zas, the legendary birthplace of Zeus. Finish your swim under the moon in Agios Prokopios, where the beach glows like stardust.
Day 2Naxos - Donoussa
Get away to Donoussa, a little treasure in the Small Cyclades. She is asleep. Anchor at Kedros Beach, hiking to Kalotaritissa's wildflower-choked ruins or snorkelling its azure seas. Dine at a beach shack on gouna, sun-dried mackerel, toes in the sand, stars overhead.
Day 3Donoussa - Amorgos (Aegiali Harbor)
Sail to Amorgos, where the Monastery of Hozoviotissa is cliff-clinging under protection. Under a sky ablaze with stars, dive the crystal waters of the Olympia shipwreck and then toast with psimeni raki, honey-spiced spirit.
Day 4Amorgos - Koufonissi
Koufonissi says simplicity in a whisper. Boat to Kato Koufonissi's lonely coves after swimming at the powdered sugar beaches at Pori Beach. Breakfast at a harborside taverna on astakomakaronada, or lobster pasta, the catch hauled in at daybreak.
Day 5Koufonissi - Schoinousa
Drop Anchor at Mirsini Harbor of Schoinousa. After the gradient blues of Snorkel Tsigouri, climb to Panagia Church for 360° Aegean views. Dinner is coming. Under a Milky Way chandelier, tomato keftedes and crisp white wine taste great.
Day 6Schoinousa - Irakleia
Find Irakleia, swimming the shimmering depths of the Blue Cave. Wander olive gardens toward the pirate-haunted ruins at Kastro. If timing is perfect, dance at a panigiri celebration while carrying hand-held honey-drenched loukoumades.
Day 7Irakleia - Santorini (Vlychada Marina)
Race to Ios for a fast swim at Mylopotas Beach, then sail to the volcanic drama of Santorini. Eat fava with capers while Oia's domes radiate in the dusk; dock in Vlychada, kayak Red Beach's rust-hued shoreline.
Day 8Santorini - Folegandros
Trade people for the peace of Folegandros' cliffside. Trek to Panagia Church, the Aegean expanse below, then eat matsata pasta in a courtyard illuminated by lanterns with wild goat ragù.
Day 9Folegandros - Milos
Milos dazzles with rainbow harbours and moon bays. In Plaka's pastel hamlet, kayak Sarakiniko's bone- white cliffs, swim Papafragas' caverns, and toast the day with sunset cocktails.
Day 10Milos - Sifnos
The gastronomic champion of the Cyclades, Sifnos invites you to Vathi's fjord-like bay. Trek to Chrysopigi Monastery, then in Artemonas feast on mastelo (clay-pot lamb). Not missed are pottery classes creating eternal masterpieces.
Day 11Sifnos - Serifos
Hiking Chora's whitewashed hive for revithada stew views, sail to Serifos. Still Kythnos, relaxing in the thermal springs of Loutra. Eat under a star-dusted sky sfougato, or cheese pie.
Day 12Serifos - Kythnos
Go back to Syros' neoclassical grace. Walk the marble streets of Stroll Ermoupoli, nibble rosewater loukoumi, then cruise to Paros. Toast your journey with xinomavro wine in Naoussa's elegant harbour.
Day 13Kythnos - Paros
One last swim at Kolymbithres' moonlike bays, then a languid brunch of koulouri in Parikia's lanes. Let the Portara temple bid you goodbye over the strait.
Day 14Paros - Check-out
"The sea always calls you back," you whisper as you disembark with salt-streaked hair and a heart full of Aegean sunshine.
