Dodecanese Sailing Explorer

Arrive in Rhodes and make your way to the marina to begin our sailing journey. This storied island blends history, culture and coastal charm. We board our gulet after 16:00 and settle into our cabins, meeting the crew and fellow guests as we prepare for the voyage ahead. If you arrive early, you can wander Rhodes Harbour – with traditional tavernas, markets and local shops – for a lively first taste of island life. You might also stroll through Rhodes Old Town, a UNESCO World Heritage Site of medieval streets and evocative architecture. We gather back on board for a relaxed welcome dinner that sets the tone for the days to come.

Departing Rhodes, we set sail for Symi, with sweeping Aegean views easing us into island life. Our first stop is Nanou Bay – a secluded cove of crystal-clear water – where we drop anchor for an unhurried swim and a spot of snorkelling. Refreshed, we continue to Symi Port, gliding into a picturesque harbour framed by tiers of colourful neoclassical houses. Once ashore, you can wander the waterfront at your own pace and choose a local taverna for dinner, soaking up the relaxed evening atmosphere.

We follow Symi’s rugged coastline towards St George Bay, the cliffs rising dramatically above the sea. Here we swim and snorkel in clear water beneath towering rock faces – a remote, memorable stop. We then continue to Panormitis Bay, arriving to a peaceful setting, and we visit the Monastery of the Archangel Michael Panormitis, an important Greek Orthodox site reflecting deep-rooted tradition.

Leaving Symi, we set a course for Akrogiali Bay, savouring open-sea views as the Dodecanese unfold around us. We drop anchor in the clear, quiet waters near Tilos for a leisurely midday swim and a relaxed pause. We then continue to Tilos Harbour at Livadia, where a calm island atmosphere awaits. You have time to explore the small harbour and local streets at your own pace for a gentle glimpse of authentic island life.

We depart Tilos across the open Aegean towards Chalki, with an early start if conditions require it. We anchor in Trakhia Bay to enjoy crystal-clear waters and a peaceful setting – you can swim and unwind before we continue. Later we sail into Chalki Port (Nimporio), where colourful buildings and a scenic backdrop offer a charming welcome.

We turn back towards Rhodes, tracing the coastline as we go. We pause at Anthony Quinn Bay, where turquoise water and a dramatic shoreline live up to the bay’s celebrated name. Keeping close to the coast, we continue towards Kalithea, passing pretty coves and striking rocky inlets. At Kalithea Beach we drop anchor – you can swim in the clear water or simply relax by the sea and take in the area’s natural beauty and sense of history. As evening falls, we gather on board near Rhodes for a special farewell dinner – a fitting finale to our days afloat.

We return to Rhodes New Marina, completing our sailing loop. We step ashore to explore Rhodes Old Town – a UNESCO World Heritage Site – where medieval streets and historic architecture offer a vivid glimpse into the island’s past.

We savour a final breakfast on board in Rhodes, taking in the marina views – a gentle close to our time at sea. We disembark from the gulet at 09:00, bidding farewell to the crew and fellow guests as the journey comes to a close.