Rhodes - 14 days
Day 1
Rhodes - Symi
Day 2
Symi - Nisyros (Pali)
Day 3
Nisyros - Kos
Day 4
Kos - Leros
Day 5
Leros - Patmos
Day 6
Patmos - Lipsi
Day 7
Lipsi - Levitha
Day 8
Levitha - Kalymnos
Day 9
Kalymnos - Astypalaia
Day 10
Astypalaia - Tilos
Day 11
Tilos - Chalki
Day 12
Chalki - Lindos (Rhodes)
Day 13
Lindos - Rhodes Town
Day 14
Rhodes - Check-out
Detailed Itinerary by days
Day 1Rhodes - Symi
Starting your journey in Rhodes, where mediaeval walls murmur stories of knights, Sail to Symi, a jewel-box harbor of neoclassical homes set against ochre and peach. Climb 500 steps to the Panormitis Monastery, its bells ringing above turquoise seas, then eat symian shrimp in a riverside taverna as evening gilds the bay. Arriving early will help you to avoid the monastery's noon throngs.
Day 2Symi - Nisyros (Pali)
Glide to Nisyros, where the ground still breaths. Trekking the Stefanos crater, its sulfur vents hissing underfoot, you meander around Mandraki's cobblestone paths surrounded by cobalt-domed churches. Then sip soumada (almond drink) beneath a village pergola after soaking in hot springs at Loutra. Local capers famed from volcanic soil are not missed!
Day 3Nisyros - Kos
Sail to Kos, the Hippocrates birthplace. Wander over the ancient Asklepion remains, then chill off at the thermal springs at Therma Beach. Join neighbors on Platia Platanou for kleftiko, slow-cooked lamb, under a 2,400-year-old plane tree by night. Pro tip: Hire an e-bike to investigate secret beach paths.
Day 4Kos - Leros
Park your boat at Leros, the Aegean's Art Deco masterpiece. Paddle a kayak to the WWII seaplane hangars and then go to the Byzantine paintings at the Castle of Panagia. Enjoy pitaroudia, a type of chickpea fritters, while watching the fishing boats bobbing around in the pastel harbor of Agia Marina. The spectral submarine facility in Lakki is a secret location.
Day 5Leros - Patmos
Patmos, the island of revelation, is your destination. St. John foretold the end of the world in the Cave of the Apocalypse; after you swim on the golden sands of Psili Ammos, you may descend into the cave. Savor mastiha cocktails as the sun sets in Chora's white maze, painting the sky a beautiful shade of pink. Peruse the patmian honey selection at the family-run Melisses, a hidden treasure in the area.
Day 6Patmos - Lipsi
Sail to Lipsi, a slumbering archipelago where goat numbers exceed human count. Anchors in Aspronissi Bay snorkel over seabeds covered with amphorae. If time works, feast on lipsiako cheese smeared with thyme honey then dance at Panagia tou Harou's summer festival. Not missed is the little Chapel of Panagia on a single rock.
Day 7Lipsi - Levitha
On Levitha, population 6. Unplug totally. Help shepherds gather goats, then explore the crystal seclusion of Ammoudi Bay. Under a Milky Way so brilliant it throws shadows, dine on astakomakaronada, or lobster pasta. Bring cash; no ATMs; simply stars and simplicity.
Day 8Levitha - Kalymnos
Rush into Kalymnos, where cliffs resist gravity. See sponge divers carry riches from the deep or scale the limestone "Grande Grotta." In Pothia, eat mououri—stuffed squid—after toast with foustalini liquor. Rent equipment at "Greek Kalymnos" store to find climbers' nirvana.
Day 9Kalymnos - Astypalaia
Sail to Astypalaia fashioned like a butterfly. Wander Chora's Venetian castle, the flag flying over whitewashed cubes. swim at Vatses Beach, then feast at Kaminakia Taverna on ladenia, or tomato pie. History buffs: The old "kastro" on the island reveals Roman mosaics.
Day 10Astypalaia - Tilos
Anchor at the lush haven amid the parched Dodecanese, Tilos Trekking the Monastery of Agios Panteleimonas, the bells resound over wild peacock region. At the ghost town taverna of Mikro Chorio, eat mizithra cheese. Eco-tip: Tilos runs entirely on renewable energy—sip organic wine guilt-free.
Day 11Tilos - Chalki
Drift to Chalki without cars, where donkeys still run the port. After seeing the technicolour fish at Snorkel Pontamos Cove, ascend the Knights' Castle for a sunset above Asia Minor. Must-try at Taverna Giorgos pougia, sun-dried octopus.
Day 12Chalki - Lindos (Rhodes)
See Rhodes again via Lindos, its city shining like a marble crown. Trek the donkey road to the old columns, then drop into St. Paul's Bay. Dine on melekouni (sesame-honey bars), atop a rooftop taverna, the Aegean breeze dancing through your hair. Steer clear of throngs; see the city at sunrise.
Day 13Lindos - Rhodes Town
Love the medieval grandeur of Rhodes. Walk the Street of the Knights, then negotiate for amber in the bazaar in Old Town. At Marco Polo Café, where Byzantine walls meet bohemian ideas, cap the journey with pitaroudia, or chickpea snacks. Cocktails in the secret patio of Socratous Garden last-night splurge.
Day 14Rhodes - Check-out
Set sail as the dawn over Rhodes paints the waves with the heritage of the Colossus. Get your last koulouria (sesame rings) from a street vendor; they're sweet, salty, and inextricably linked to the enchantment of the Dodecanese. Until we meet again, farewell!