Set sail across the sun-drenched waters of the southeastern Aegean and explore the Dodecanese. A constellation of islands where time-honored traditions, dramatic landscapes, and layers of history come vividly to life. From walking inside the heart of a steaming volcano to wandering the cobbled lanes of medieval towns, each stop reveals something different: a sense of time slowed, a window into sacred heritage, or simply the beauty of sailing through some of Greece’s most storied seas.
Day 1: Kos → Nisyros (~20 NM)
Anchor at: Mandraki Harbor
Highlights: Volcano hiking | Crater walk | Cliffside monastery dinner
Your journey begins with a sail to the island of Nisyros, one of the Aegean's youngest and most fascinating volcanic formations. Disembark and descend into the Stefanos crater, where a surreal, lunar landscape awaits, alive with steam vents and the scent of sulfur. Afterwards, visit Panagia Spiliani, a serene monastery perched above Mandraki. Evening finds you sipping ouzo at a tavern overlooking the caldera, where volcanic power meets island stillness.
Day 2: Nisyros → Tilos (~18 NM)
Anchor at: Livadia Bay
Highlights: Monastery hike | Mikro Chorio ruins | Quiet harbors
A tranquil morning sail leads you to Tilos, an island where nature and heritage blend harmoniously. Explore the abandoned village of Mikro Chorio, where crumbling stone homes echo with stories of the past. Or hike up to the Monastery of Agios Panteleimonas, surrounded by pine trees and peace. The pace is unhurried, the harbors uncrowded, and the night skies brilliantly clear.
Day 3: Tilos → Chalki (~15 NM)
Anchor at: Nimborio Harbor
Highlights: Ftenagia Beach | Seaside dining | Neoclassical charm
Short in distance but rich in beauty, the sail to Chalki is a feast for the eyes. The island’s neoclassical harbor glows in soft pastels, welcoming you to its slow rhythms. Spend your day swimming at Ftenagia Beach, followed by a lobster dinner beneath the medieval clocktower, with music from the tavernas drifting on the breeze.
Day 4: Chalki → Alimia (swim stop) → Rhodes (~22 NM)
Anchor at: Rhodes Old Town Marina
Highlights: Ghost island swim | UNESCO heritage | Medieval discovery
Begin with a swim stop at Alimia, a deserted island perfect for snorkeling. Then cruise onward to Rhodes, where past and present collide beautifully. Explore the Palace of the Grand Master, medieval alleyways, and Ottoman minarets inside the UNESCO-listed Old Town. It’s one of the best-preserved medieval cities in the world and it feels like stepping into a living history book.
Day 5: Rhodes → Symi (~24 NM)
Anchor at: Gialos Harbor
Highlights: Neoclassical facades | Panormitis Monastery | Hidden beaches
Sail into the colorful wonder of Symi, where 19th-century mansions climb up from the sea in a dramatic cascade. Visit the revered Panormitis Monastery, known for its beautiful iconography, or discover quiet coves like Nanou Bay, ideal for a dip and a dose of sun-soaked serenity. The island’s elegance and spirit are timeless.
Day 6: Symi → Kalymnos (via Gyali) (~32 NM)
Anchor at: Pothia Harbor
Highlights: Climbing capital | Gyali swim | Sponge diving history
A longer sail includes a volcanic swim stop at Gyali before arriving in Kalymnos, famed for both sponge diving heritage and its global reputation as a climber’s paradise. From the limestone cliffs of Masouri to the island’s labyrinth of walking trails, adventure awaits on land and sea alike. Evenings in Pothia are filled with local color, culture, and delicious meze.
Day 7: Kalymnos → Kos (~18 NM)
Swim Stop: Pserimos Bay
Return: Kos Marina
Highlights: Farewell swim | Kos Old Town stroll | Final Aegean sunset
Sail back toward Kos, pausing for one last swim at Pserimos. Celebrate the end of your voyage with lunch at a seaside tavern and optional stroll through Kos Old Town, where ancient ruins and harbor lights mark your journey’s end.
Chart Your Dodecanese Story
From volcanic heartlands and monastic strongholds to medieval ports and pastel-painted harbors, the Dodecanese islands offer a sailing experience like no other. Adventure, serenity, and discovery converge across every nautical mile.
Your Dodecanese story begins here. Are you ready to live it?
