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The saying "Life is about the journey, not the destination" often applies to self-help and mindfulness. However, after a 10-night Dodecanese island-hopping familiarisation trip, I can confidently say it's about both. My journey involved several ferries, and each boarding was filled with eager anticipation. I shared the decks with other tourists, locals laden with produce, and even a few canine companions, making for a vibrant microcosm of life sailing towards numerous island destinations.
My island hopping adventure began in Rhodes, exploring the impeccably preserved medieval Rhodes Town. Its captivating contrast to the coastal village of Lindos, my next stop on the island's southeastern coast, was striking. Lindos, a historic gem, offers awe-inspiring vistas of St. Paul's Harbour, making it an ideal starting point before venturing down its charming cobblestone alleyways, adorned with flower-laden courtyards and quaint tavernas.
Next, I discovered Tilos, a hidden treasure among the Greek islands and one of the lesser-visited gems. It offers exceptional opportunities for scenic walks and enchanting seascapes. My island-hopping journey then led me to Symi, renowned for its stunning Monastery of Panormitis. Symi's harbour, a vibrant spectacle of colours, proudly stands as one of the most picturesque and visually appealing island within the entire archipelago.
Just an hour from Rhodes lies Halki, often called the "Island of Peace." This gorgeous island remains untouched by mass tourism, with very few cars, ensuring that tranquility reigns supreme during any stay.
For the final four islands of my trip Lipsi, Kalymnos & Telendos and Leros, I boarded a ferry from the port of Rhodes. The four-hour sailing to Lipsi was made pleasant by the comfortable, air-conditioned cabin, complete with a snack bar and outdoor seating area, making the journey feel much quicker.
Lipsi is a tiny island, only 8 kilometres long and sparsely populated, with just 800 residents concentrated in the single village at the port of arrival. With few cars in circulation, the island can be explored on foot, or by water taxi to reach its most beautiful beaches.
Kalymnos boasts a rich maritime heritage, with its history as a hub for sponge diving deeply woven into its identity. Its turquoise bays and charming harbours are a testament to its enduring connection with the sea. A mere ten-minute boat crossing away, the car-free islet of Telendos beckons with its serene ambiance, making it an ideal spot for a day trip or a longer stay.
The last island on my trip was Leros, one of the most underrated islands. It is quite small and has remarkably retained its unique character. Its Italian influence has endowed the island with a wonderful personality, and a visit to the island's war museum proved to be a surprisingly emotional highlight before I returned to Rhodes, completing a truly memorable journey through the Dodecanese islands.
Rhodes is the largest and most popular island of the Dodecanese. It is located in the south eastern edge of Europe between the Aegean Sea and the coast of Turkey. It is an island of many contrasts and a combination of tradition and contemporary aesthetics, blending ancient and medieval monuments with modern architecture.
Tilos combines nature with tradition and an ancient past. The beautiful natural scenery and the tranquil island vibes captivate every visitor. This is an island with green hills, fertile valleys with clear springs and a variety of flowers and birds. The whole island is an open eco-park. It has picturesque villages and magnificent, tranquil beaches.
At the edge of the Aegean Sea, between Rhodes and the Turkish coastline, lies a small island that will enchant you with its glamour and grace, Symi. Many call it the 'jewel of the Dodecanese'. Its beauty captivates every visitor at first sight. The colourful traditional restored houses that spread amphitheatrically up to the top of the hill in combination with the deep blue of the sea, creates a unique and unforgettable landscape.
One of the smallest islands of the Dodecanese, Halki is located between Rhodes and Tilos. It is an island full of charm and hidden treasures. Once you reach the port, you will be greeted with a beautiful, picturesque scene, straight from a postcard. The absence of vehicles, the calmness and the romantic atmosphere this island radiates, are all the essentials for a relaxing holiday.
Located between Patmos and Leros, Lipsi (or Leipsoi) is a small island of the Dodecanese. Its remote location and small size have caused the island to remain relatively unnoticed by mass tourism, preserving its unspoiled natural landscape, unspoiled seashores and traditional character of its main town. Hiking, swimming or simply relaxing on the seashore are your go-to activities when visiting Lipsi.
Kalymnos is an island that combines the charm of steep mountain peaks with the beautiful coastline and crystal clear waters. Here the art of sponge-diving flourished while today it offers both peaceful and adventurous holidays by climbing towering cliffs or diving in a sea bed of ancient shipwrecks. The distinctive island of Telendos, lying just a kilometre off the mid- western shore, is a step back in time. Easily reached from Myrties in just ten minutes by water-taxi, there is one tiny fishing hamlet and a number of sand-shingle beaches.
Leros is a picturesque and charming island, offering a unique blend of serenity, beauty, and traditional life. Its stunning landscapes, characterised by low hills and flatlands that meet the sea, create a relaxing paradise. This tranquil setting stands in stark contrast to the island's past during the Second World War. Visitors can explore the impressive War Museum of Leros, housed in a former wartime tunnel, which showcases a variety of historical artefacts.
12th August 2025
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