Mykonos - Naxos - Paros - Kea
Day 1
Mykonos (Tourlos Marina) - Naxos
Day 2
Naxos - Paros (Parikia Harbor)
Day 3
Paros - Milos (Adamantas Port)
Day 4
Milos - Sifnos (Kamares Harbor)
Day 5
Sifnos - Serifos
Day 6
Serifos - Serifos
Day 7
Serifos - Kythnos (Merichas Port)
Day 8
Kythnos - Kea (Korissia/Vourkari)
Day 9
Kea - Andros (Batsi Port)
Day 10
Andros - Tinos
Day 11
Tinos - Tinos
Day 12
Tinos - Syros (Ermoupoli Port)
Day 13
Syros - Mykonos (Tourlos Marina)
Day 14
Mykonos - Check-out
Detailed Itinerary by days
Day 1Mykonos (Tourlos Marina) - Naxos
Under the famous Portara, a marble entryway of Apollo's temple, sail from Mykonos' glitter to Naxos. Then eat kitro-glazed pork in a mountain taverna from Zeus's legendary birthplace, Mount Zas. Finish with a moonlit swim in Agios Prokopios, where the sand glistens like crushed diamonds.
Day 2Naxos - Paros (Parikia Harbor)
Sail to Parikia, the busy Parasian. Discover the Byzantine Panagia Ekatontapiliani then stroll across Naoussa's fashionable harbour for octopus souvlaki. Explore the lunar rock pools of Kolymbithres or taste Assyrtiko wine from a vineyard fashioned from old marble. Sailor tip: Anchor early; Paros fills quickly.
Day 3Paros - Milos (Adamantas Port)
Follow the horizon toward the volcanic paradise Milos. Duck in Klima's rainbow syrmata, kayak Sarakiniko's bone-white coves, and snorkel Papafragas' sea caves. Feast on grilled octopus at Mandrakia, where candy-like fishing cottages hang over the rocks.
Day 4Milos - Sifnos (Kamares Harbor)
The culinary queen of the Cyclades, Sifnos greets you with golden shores and clay-pot magic. Clutching a sea-split rock, hike to the Chrysopigi Monastery and then have mastelo (lamb slow-cooked in red wine) in Artemonas. Don't miss hillside taverna's chicken croquettes.
Day 5Sifnos - Serifos
Swap Sifnos' shine for Serifos' rough beauty. Anchor in Livadi, a stretch of golden sand, and walk the zigzag path to Chora, a cluster of whitewashed cube houses. Revithada (lemon chickpea stew) for lunch with views of the cliffs—this is Greece at its most basic.
Day 6Serifos - Serifos
Free day to enjoy secrets of Serifos. Snorkel Vagia Beach, swim in Psili Ammos, or climb to the abandoned mines owned by Mega Livadi. Dine at a cliffside kafeneio, where residents argue politics over bitter coffee while the Aegean is gold painted by the sunset.
Day 7Serifos - Kythnos (Merichas Port)
Sail to Kythnos; there simplicity rules. Soak in Loutra's thermal springs (the preferred choice of Byzantine emperors) or sliver of beach separating twin bays Kolona Beach. Dinner is here. Under a sky studded with stars, grilled sfougato, or cheese pie, tastes great.
Day 8Kythnos - Kea (Korissia/Vourkari)
Kea says wild beauty. After hiking to the Lion of Kea from the sixth century, dive the WWII wreck Brittany at night. Anchor at V ourkari for beachfront restaurants offering lobster smothered in garlicky butter. Local secret: To soothe the soul is Rakomelo, honey-spiced brandy.
Day 9Kea - Andros (Batsi Port)
The rich outlier of the Cyclades, Andros welcomes you with stone arches and waterfalls. After hiking to Pithara Falls, stray Chora's marble alleyways where modern art galleries collide with medieval structures. Feast at a beachside kafeneio on froutalia, a herb-packed omelette.
Day 10Andros - Tinos
Sail to Tinos where workmanship meets spirituality. Pilgrims crawl to the Panagia Evangelistria, although Pyrgos village has marble marvels for hunting. Lunch in a patio shaded by bougainvillea on artichokes à la polita.
Day 11Tinos - Tinos
Free day to search Tinos' soul. The boulder-strewn terrain of Trek V olax, surf Kolymbithra Beach, or sip ouzo in hilltop vineyards Falatados. Finish at sunset in Agios Fokas, as the sea reflects the vivid color of the sky.
Day 12Tinos - Syros (Ermoupoli Port)
Syros dances with the neoclassical grandeur of Ermoupoli. Wander marble-paved lanes to Miaouli Square, humming with shops and rosewater loukoumi smell. After seeing sunset, climb Ano Syros and then sink into a gritty rembetiko pub for deep Greek blues.
Day 13Syros - Mykonos (Tourlos Marina)
Go back to Mykonos and pass by Delos' holy sites. By 17:00, then squeeze in a last swim at Agios Ioannis where the sea blues pink at sunset. Little Venice's lobster pasta will help you toast your voyage under windmills until dawn.
Day 14Mykonos - Check-out
Get off the boat with salty hair, a heart full of Cycladic light, and a promise to the horizon: 'This isn't goodbye.' After one last espresso at Klimataria Taverna, the taste of excitement is still on your tongue.