Kos - 14 days
Day 1
Kos Marina - Kalymnos
Day 2
Kalymnos - Leros
Day 3
Leros - Patmos
Day 4
Patmos - Fourni
Day 5
Fourni - Lipsi
Day 6
Lipsi - Levitha
Day 7
Levitha - Astypalaia
Day 8
Astypalaia - Nisyros
Day 9
Nisyros - Tilos
Day 10
Tilos - Chalki
Day 11
Chalki - Rhodes
Day 12
Rhodes - Symi
Day 13
Symi - Kos
Day 14
Kos - Check-out
Detailed Itinerary by days
Day 1Kos Marina - Kalymnos
Starting your journey in Kos Marina, where contemporary yachting meets historic ruins, Sail to Kalymnos, the "Sponge Diver's Island," whose sharp cliffs call for mountaineers. Explore the Byzantine remnants of Hrysocheria Castle or plunge into Vathy Bay's turquoise seas. Feast in Pothia's harbour on mououri, or stuffed squid. To find secret beaches like Kandouni, rent a scooter.
Day 2Kalymnos - Leros
From WWII, glide to Leros, a time capsule. Kayak to Lakki's Art Deco submarine station; then, climb to Panagia Castle for sunset across Agia Marina's pastel port. Dine at a beachfront taverna on pitaroudia, or chicken fritters. Secret spot: Zero crowd blue seas at Xerokambos Beach.
Day 3Leros - Patmos
See Patmos, the "Island of Revelation." See St. John writing the last chapter of the Bible descending into the Cave of the Apocalypse. Swim in the golden sands of Psili Ammos, then drink mastiha cocktails in Chora's winding lanes. Must-try Melisses farm's Patmian honey.
Day 4Patmos - Fourni
Anchor at Fourni, a rough archipelago once used for pirate hide-out. Then eat astakomakaronada (lobster pasta) in Kambi's fishing village after hiking to Christos Chapel for panoramic Aegean views. Local gem: See a Fourni craftsmen for hand-carved wooden boats.
Day 5Fourni - Lipsi
Drift to Lipsi, an eight-islet quiet jewel. After the shipwreck of Snorkel Aspronissi Bay, savor lipsiako cheese sloshily topped with thyme honey. If timed well, folks dance till dawn at the Panagia tou Harou event. For sunrise, visit Church of Panagia on a single rock.
Day 6Lipsi - Levitha
On Levitha, the population is 6. Unplug here. Help herders herd goats, then enter the crystal seclusion of Ammoudi Bay. Live beneath a Milky Way so brilliant it creates shadows. Pack cash; there are no ATMs; just stars and simplicity.
Day 7Levitha - Astypalaia
Sail to Astypalaia fashioned like a butterfly. Wander Chora's Venetian castle then swim at the pebbled coves of Vatses Beach. Feast at Kaminakia Taverna on ladenia, or tomato pie. Readers of history: Search close to Mesa Nisi for Roman mosaics.
Day 8Astypalaia - Nisyros
Rising to Nisyros, the ground still boils. Trek the Stefanos Volcano; its sulfur vents hissing like dragons; then relax in Loutra's thermal springs. Not missing are the black-pebble mosaics and caper vendors from Nikia Village.
Day 9Nisyros - Tilos
Anchor at the first zero-waste island in Greece, Tilos After wild peacocks wander Agios Panteleimonas Monastery, eat at the ghost village taverna run by Mikro Chorio. Eco-win: Drink organic wine from solar-powered vineyards run by Tilos.
Day 10Tilos - Chalki
Sail to Chalki free of cars, where cobbles are dominated by donkeys. After seeing the colorful fish at Snorkel Pontamos Cove, ascend Knights' Castle for a sunset over Turkey. Must-eat at Taverna Giorgos is Pougia, sun-dried octopus.
Day 11Chalki - Rhodes
Go back to Rhodes, where mysteries of the Old Town are guarded by mediaeval walls. Walk the Street of the Knights then dive into Anthony Quinn Bay. Cocktails in the secret courtyard at Socratous Garden last night.
Day 12Rhodes - Symi
Hop to the pastel paradise Symi. Trekking to Panormitis Monastery, then swim at Nanou Beach Feast on symian shrimp in Gialos Harbor. Tip: Yiannis dives for sponges himself; buy them from his store.
Day 13Symi - Kos
Tracing the Anatolian coast, sail back to Kos. Cycle the old paths of the Asklepion then relax at the hot springs of Therma Beach. Under the 2,400-year-old plane tree of Kos Town, Kleftiko lamb sits final feast .
Day 14Kos - Check-out
Say goodbye with koulouria, which are sesame rings from a bakery on Kos. The salty, sun-drenched, and unchanging magic of the Dodecanese stays with you like a siren's song. Have a great day until next time!