Welcome to the top of the “twelve islands”, an archipelago revered for its storied past, secret bays and sense of discovery. Director and founder of Sailing Collective charters, Dayyan Armstrong shares the local intel.

The far eastern islands of Greece lean toward Turkey, so close in places that only a few short tacks separate them. Here, in the Dodecanese Archipelago, the Greek islands take on a different personality entirely – distinct from the widely known Cyclades to the west. Grand peaks rise sharply against the horizon, their barren slopes brushed with a warmer, earthier hue than the familiar blue-and-white palette of the Aegean.

Their history is layered and complex. Byzantine kingdoms once thrived here, only to cede control to the Ottomans, then the Italians, the modern Turkish state, and finally, Greece itself. This shifting sovereignty left an indelible mark on the architecture, cuisine and culture. Cut off from mainland Greece and bypassed by the tourist crowds that flood the Cyclades, the northern Dodecanese remain a frontier for yacht charters – a place where the waypoints are few, the hidden bays many and the journey still feels like an act of exploration.

Kos

Kos is the second-largest island in the Dodecanese Archipelago and the primary hub for the northern islands. Located just 12 nautical miles from the Turkish city of Bodrum with daily ferry service, Kos serves as the main resource port and jumping-off point for the rest of the island cluster. Ashore, there are ample provisioning opportunities for yachts of all classes. The main port lies along the east coast, while an international airport on the opposite side of the island makes Kos an obvious choice for both entry and disembarkation for charters. Superyachts can anchor off the town, and Kos Marina offers transient berths for both charter boats and private yachts.

Kalymnos

Kalymnos lies north of Kos and is a common departure point for sailors heading in that direction. It’s large, with rustic villages. Off the west coast, the small island of Telendos sits just across from the village of Masouri, separated by a narrow channel. Along Telendos’s coast, a small village clings to the shoreline, maintaining a timeless feel. Anchor along the channel and spend an afternoon taking in the superb view of both the colourful village and mountain range along Kalymnos.

North of the channel is a wide bay that includes Arginonta to Emporios. The coastline is largely uninhabited with a handful of monasteries perched along the sloping peaks. These western-facing cliffs catch the soft light of the setting sun in the early evenings, creating a dramatic and serene landscape. Yachts can easily find secluded areas to anchor here.

Further north, Palionnisos Bay offers a spacious and sheltered anchorage with a sparsely populated shoreline. Approximately 20 moorings are available for vessels up to 20 metres long, while larger yachts can anchor in deeper water farther out. On the north side of the bay, Taverna Ilias provides an attractive stop ashore, serving simple, authentic foods in a traditional setting.

Leros

In recent years, Leros has become increasingly popular, offering a strong challenge to the renowned Patmos as the area’s premier island. Located north of Kalymnos and with major historical significance, the town of Lakki was renovated by Mussolini during the first quarter of the 20th century, during the Italian occupation (1912–1943) of the Dodecanese Islands. The architectural style of Lakki reflected the vision for an Italian-run Mediterranean, marked by imposing symmetry and austere grandeur. Today, Lakki is home to one of the largest protected bays in Greece.

Opposite Lakki, on the east coast of Leros, several scenic coastal towns line protected bays. Panteli is one of the key destinations for yachts; the cove is large and deep, allowing Superyachts to anchor offshore while sailing yachts and motor yachts up to 40 metres long can anchor stern-to along the coast. The town is filled with classic Greek character including many windmills perched on high. The citadel towers overhead, located at the island’s highest point. Panteli is also dense with shops, cafés and restaurants worth trying. There are several moorings in the bay that accommodate vessels up to 20 metres long, and smaller yachts can anchor south of town, off Vromolithos Beach.

Nearby Alinda is a large and peaceful anchorage. Upscale beachfront hotels and houses lie along the water’s edge, along with Mylos By The Sea, a long-time and well-loved restaurant located on the southern shore. Yachts can anchor in the southern bay between Mylos and the town quay, maintaining distance from the designated swimming beach.

Patmos

Continuing onward from Leros, the northernmost island of the Dodecanese is renowned among owners accustomed to elegance and late-night gatherings. Limin Skala Patmos is the main port of Patmos and the island’s hub. The quay extends along the town and can accommodate a wide range of vessels up to 40 metres long. Primarily sailboats and catamarans dot the docks, along with gulets, sailing yachts and mid-sized motor yachts stern-to. Larger yachts can anchor in the bay.

Similar to the rest of the Dodecanese Archipelago, Patmos holds notable Roman and Byzantine significance. It is famously the site where St. John the Apostle, also referred to as John of Patmos, wrote the Book of Revelation, inspired by visions he received while on the island. Patmos served as a penal colony for the Romans; John was banished there in 95 AD by Emperor Domitian for his religious beliefs. Later, Patmos became an important Byzantine military base, characterised by the imposing Monastery of Saint John the Theologian, perched like a crown atop the hill of Chora – the tallest peak on the island – visible from miles away.

Ormos Grikou lies two miles south of Skala and offers a quieter anchorage away from the thriving port. Protected by an island at the head of the bay, Grikou is surrounded by stunning architecture and prominent homes. The Patmos Aktis, a Luxury Collection Resort & Spa, is a five-star hotel located along the beachfront of Grikou Bay, with a dinghy dock situated in front. It offers fine dining as well as a private beachside pool, with easy access to taxis for exploring the rest of the island.

Chora, a lively town located around the Holy Monastery of Saint John the Theologian, comes alive at night. The imposing walls of the monastery are illuminated and can be seen from anchorages all across Patmos. The ancient village thrives with restaurants scattered throughout the resilient citadel.

Lipsi

Finally, Lipsi lies just 10 nautical miles east of Patmos. Small and rustic, the island offers a quieter, more authentic experience with numerous calm bays hugging its southern coast. Only 8 kilometres in length and home to approximately 800 residents, Lipsi feels like a refreshing retreat for yachters seeking to check out the less-travelled waypoints of the Dodecanese Archipelago. Although it’s just a short sail from Patmos, the island is remote. A network of trails weaves through the village, which can be discovered either on foot or by guided horseback rides. Olive groves and vineyards speckle the landscape, and visitors can find a small winery nestled in the hills near the honey farm and the Philip Hill Art Gallery.

The main port of Lipsi features a jetty that accommodates yachts up to 30 metres long. Moorings are available in the southern harbour, while bigger vessels may choose to anchor in the main bay or nearby Sokora. Prevailing winds come from the northwest, with occasional gusts from the north.

Ormos Kouloura, a large, secluded bay east of the main port, offers a great anchorage for those seeking quiet and protected waters. There’s a beach and the single, much celebrated Dilaila Restaurant, a family-run taverna that serves fresh seafood and provisions sourced from the island at lunchtime (it’s closed for dinner), known for its creative takes on local dishes. Limited moorings are available, and the location’s depth comfortably accommodates yachts of all sizes. While Ormos Kouloura offers good shelter from the strong meltemi winds, it remains open to the south.