Crossroads of Civilisations: The Dodecanese

Sacred islands, layered history, and a more expansive Aegean journey

Introduction

The Dodecanese offers a journey through history and colour: medieval Rhodes, pastel-hued Symi, volcanic Nisiros, and tranquil isles where life moves slowly. This sailing adventure blends ancient legacies, vibrant harbours, and peaceful coves along Greece’s eastern frontier.

Start Your Journey

Itinerary Overview

Total Distance: 170 nm | Average Daily Sailing: 3-4 hrs

A coastal scene with white buildings on a hillside, a fortress on top, and a beach with umbrellas and people swimming in the water.

Day 1 - Rhodes

Begin in Rhodes, famed for its medieval Old Town, a UNESCO World Heritage site. Wander cobbled streets lined with knights’ palaces, enjoy shopping in lively markets, or relax at waterfront cafés before casting off from one of the Aegean’s great historic ports.

Colorful houses along a hillside next to a deep blue sea with boats docked at the shore, mountainous landscape in the background under a partly cloudy sky.

Day 2 - Symi

Symi is unforgettable with its neoclassical mansions cascading down to a dazzling harbour. Once known for sponge diving, today it charms with colourful houses, boutique shops, and harbourside tavernas. Its blend of elegance and intimacy makes it one of Greece’s most photogenic stops.

A coastal town with white buildings on a hillside, blue water in the foreground, and a sailboat on the water. A hill with some structures is in the background under a clear blue sky.

Day 3 - Nisiros

A volcanic gem, Nisiros is small but dramatic. The highlight is its steaming caldera, where paths wind across a lunar-like landscape. In Mandraki, narrow alleys, monasteries, and whitewashed houses evoke a traditional Greek island atmosphere far from the crowds.

A white castle-like building with a tower, palm trees, parked cars, and a stone wall along a beach with clear blue water and a bright sky.

Day 4 - Kos

Kos mixes sandy beaches with layers of history. Visit the ancient Asklepion healing sanctuary, cycle along palm-lined avenues, or relax in the island’s many beach clubs. Kos Town offers lively cafés, a medieval castle, and the energy of one of the Dodecanese’s main hubs.

A scenic harbor with several sailboats docked and white buildings with blue accents along the shoreline, set against a hilly, arid landscape under a clear blue sky.

Day 5 - Tilos

Peaceful and unspoiled, Tilos is an island of nature reserves and sleepy villages. Stroll quiet lanes in Megalo Chorio, swim in secluded coves, and discover its wild beauty. With little development, Tilos feels like a step back in time to a gentler Greece.

A coastal town with colorful houses, boats docked along the waterfront, and a white church with a tall steeple against a bright blue sky.

Day 6 - Halki

Halki enchants with pastel houses around a tranquil harbour. Smaller and quieter than neighbouring Rhodes, it’s perfect for leisurely walks, authentic tavernas, and dips in crystal-clear waters. Its calm rhythm and picturesque beauty make it an idyllic final island stop.

Medieval stone castle with illuminated walls and a bridge at dusk, clouds in the sky.

Day 7 - Rhodes (Return)

Return to Rhodes for a last stroll through its medieval streets or a visit to the Palace of the Grand Master. Reflect on a voyage of colourful harbours, volcanic landscapes, and timeless island life in this captivating corner of the Aegean.

Continue Your Journey

Explore our yachts that brings this itinerary to life, or view the sailing route in more detail.

See Our Yachts for This Itinerary
View Interactive Route on Google Maps

Optional Onshore Experiences

Enhance your voyage with hand-picked experiences ashore, blending the region’s rich culture with its celebrated cuisine.

A nighttime scene of a lively city square with a stone fountain in the center, surrounded by illuminated shops, cafes, and historic buildings, with people walking and sitting on the steps near the fountain.

Cultural Moments

  • Rhodes Old Town: Explore cobbled lanes, knights’ palaces, and the Palace of the Grand Master in one of Europe’s best-preserved medieval cities.

  • Nisiros Caldera: Walk across a steaming volcanic crater, where sulphur vents and lunar landscapes create one of the Aegean’s most dramatic sights.

  • Kos Asklepion: Discover Kos’ ancient sanctuary of Asklepion, once a centre of healing, set on a hillside with sweeping island views.

Colorful boats docked in a harbor with pastel buildings and hillside in the background under a clear blue sky.

Cuisine Journeys

  • Symi Seafood: Savour fresh fish and shrimp in colourful harbour tavernas, surrounded by neoclassical mansions and glittering waters.

  • Tilos Meze: Enjoy traditional meze in quiet village tavernas, where simple flavours and warm hospitality reflect the island’s timeless charm.

  • Kos Vineyards: Taste local wines from Kos, sampling varietals shaped by volcanic soils and centuries of island cultivation.

Elysian - Sailing Beyond Ordinary

Start Your Journey