Greece · 13 - 19 June 2026
Dodecanese Islands Cruise
Sail the Magical Dodecanese Islands along the Turkish Coast, these Jewels of the Aegean are an amazing groups of Islands to discover
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Overview
Sail the magical Dodecanese Islands along the Turkish coast, where the jewels of the Aegean await discovery. We offer a carefully selected range of sailing yachts and motor yachts to suit your style, group size, and budget, though our recommendation is a comfortable catamaran for the ultimate way to experience the stunning waters of the Northern or Southern Dodecanese. Cruise through enchanting islands and hidden bays, exploring destinations such as Rhodes, Symi, Kastellorizo, Chalki, Samos, Kos, Lipsi, Marathi, Patmos, Leros, and Kalymnos. Each island offers its own unique charm, from iconic harbours and authentic Greek villages to crystal-clear anchorages, rich culture, and unforgettable local flavours. Every journey is tailor-made around the interests of our guests. Whether you are seeking a sailing-intensive adventure, a holistic escape, a cultural and culinary discovery, a party-style charter, or a blend of everything, we will design the ideal itinerary for you. This route perfectly balances remote bays, authentic island life, beautiful anchorages, and the magic of the Aegean. We can also incorporate local events and festivals taking place during your charter week to make the experience even more special. Your yacht charter includes an experienced skipper, and a chef/stewardess can also be added to create a seamless and luxurious onboard experience. THE EXPERIENCE Luxury Catamarans, Sailing Yachts & Motor Yachts Swim in secluded turquoise bays Wander authentic Greek villages Sunset dinners in iconic harbours Dive into culture, cuisine & island life TAILOR-MADE FOR YOU Design your perfect charter: 🌊 Sailing Intensive 🧘 Holistic Escape 🍷 Cultural & Culinary Journey 🎉 Party Charter ⚖️ Or the perfect blend of everything ONBOARD LUXURY Experienced Skipper included Optional Private Chef & Stewardess Fully customised itinerary & experiences Access to local events & festivals
Highlights
KOS - Gateway to the Dodecanese
Kos is where your Aegean adventure begins—a vibrant island that perfectly blends ancient history, crystal-clear waters, and effortless island lifestyle. Known as the birthplace of Hippocrates, the father of medicine, Kos offers a rich cultural backdrop alongside stunning beaches and lively harbour energy. Wander through the charming streets of Kos Town, explore ancient ruins and medieval castles, or relax along golden coastlines where the Aegean sparkles in every shade of blue. From laid-back beach clubs to authentic tavernas serving fresh seafood and local flavours, Kos delivers the perfect balance of energy and escape. As a sailing hub, Kos is the ideal launch point into the Northern Dodecanese—offering easy access to untouched islands, hidden bays, and unforgettable journeys at sea.
Rhodos – Where History Meets the Aegean
Rhodos is a captivating blend of ancient power, medieval grandeur, and vibrant island life—one of the most iconic destinations in the Dodecanese. From the moment you arrive, you’re immersed in a world where history and beauty collide. Explore the UNESCO-listed Old Town of Rhodos, a living medieval masterpiece of cobbled streets, grand fortifications, and timeless atmosphere. Beyond the walls, discover golden beaches, crystal-clear bays like Anthony Quinn Bay, and the whitewashed elegance of nearby villages such as Lindos. Rhodos offers more than just history—it’s alive with energy, culture, and unforgettable experiences. From sunset dinners by the sea to exploring ancient ruins and hidden coves, every moment feels cinematic.
Symi – The Jewel of the Dodecanese
Symi is pure magic—an island of colour, elegance, and timeless charm. As you sail into its iconic harbour, you’re greeted by cascading neoclassical mansions in soft pastel hues, creating one of the most beautiful arrivals in all of Greece. Life here moves slower. Days are spent swimming in crystal-clear bays, exploring hidden coves, and wandering narrow stone pathways that reveal breathtaking views at every turn. From the lively atmosphere of Gialos Harbour to the peaceful spirituality of Panormitis Monastery, Symi offers a perfect balance of energy and serenity. Long lunches by the water, fresh seafood, local honey, and warm Greek hospitality define the experience—simple, authentic, and unforgettable.
Lindos – Iconic Beauty, Timeless Greece
Lindos is one of the most breathtaking destinations in Greece—a perfect blend of ancient history, whitewashed charm, and crystal-clear waters. Set beneath its dramatic Acropolis, this postcard-perfect village feels both cinematic and timeless. Wander through narrow cobbled streets lined with bright white houses, discover hidden courtyards and rooftop terraces, and soak in panoramic views over the Aegean. Below, swim in the turquoise waters of St. Paul’s Bay, one of the most stunning natural anchorages in the Greek islands. From sunrise explorations to sunset dining overlooking the sea, Lindos delivers a seamless mix of culture, beauty, and unforgettable moments.
Patmos – The Sacred Island of the Aegean
Patmos is a place of spiritual depth, timeless beauty, and understated luxury—an island where history, serenity, and natural elegance come together. Known as the island where St. John wrote the Book of Revelation, it carries a unique energy that sets it apart from the rest of the Dodecanese. At its heart lies the UNESCO-listed Monastery of St. John, towering above the whitewashed village of Chora, with winding alleys, hidden courtyards, and panoramic views across the Aegean. Below, a collection of pristine bays and beaches offer crystal-clear waters perfect for swimming, anchoring, and pure relaxation. Patmos is not about crowds or noise—it’s about atmosphere, authenticity, and quiet sophistication. Long lunches by the sea, sunset moments in peaceful harbours, and a sense of calm that stays with you long after you leave.
Kastellorizo – Greece at the Edge of the Aegean
Kastellorizo is one of Greece’s most remote and enchanting islands—a place of raw beauty, vibrant colour, and true escape. Sitting on the edge of the Aegean near the Turkish coast, it feels like a world of its own. Arriving into its tiny harbour is unforgettable, with a perfect line of colourful waterfront houses reflected in crystal-clear water. Life here is slow, simple, and deeply authentic—where long lunches stretch into sunset and the rhythm of the sea sets the pace. Swim in some of the clearest waters in Greece, explore hidden sea caves like the famous Blue Grotto, and experience an island untouched by mass tourism. Kastellorizo is not about variety—it’s about purity, tranquility, and connection.
Chalki – Quiet Elegance of the Aegean
Chalki is a hidden gem of the Dodecanese—an island of simplicity, elegance, and untouched charm. Just a short sail from Rhodes, it feels a world away, where life slows down and the beauty lies in its peaceful rhythm. The island’s picturesque harbour, Nimborio, is lined with pastel neoclassical houses, calm waters, and a handful of authentic tavernas right on the sea. With no crowds and minimal development, Chalki offers a rare sense of privacy and tranquility. Days are spent swimming in crystal-clear bays, walking quiet coastal paths, and enjoying long, relaxed meals by the water. There are no distractions here—just pure island living at its finest.
Lipsi – The Essence of Simple Island Life
Lipsi is where the Aegean slows down—a small, unspoiled island defined by crystal-clear waters, quiet charm, and pure authenticity. It’s not about sights or crowds, but about feeling completely in the moment. Arriving by boat, you’re welcomed by a peaceful harbour, friendly locals, and a laid-back atmosphere that instantly shifts your pace. Spend your days swimming in some of the clearest turquoise bays in Greece, anchoring off hidden beaches, and exploring nearby islets like Arki and Marathi. Evenings are all about long, relaxed dinners by the water—fresh seafood, local wine, and simple Greek flavours that taste better in this setting than anywhere else.
Kalymnos – Raw Energy of the Aegean
Kalymnos is an island of character, adventure, and authentic Greek spirit—where rugged landscapes meet deep-rooted tradition. Known worldwide for its sponge-diving heritage and dramatic cliffs, it offers a more raw and energetic side of the Dodecanese. The coastline is dotted with striking bays and crystal-clear waters, perfect for swimming and anchoring, while inland, steep mountains and winding roads reveal incredible views and a sense of untamed beauty. The island has become a global hotspot for rock climbing, attracting adventurers from around the world. Beyond the action, Kalymnos remains deeply authentic. Bustling tavernas, lively harbour life, and warm local hospitality create an atmosphere that’s vibrant yet grounded in tradition.
Leros – Undiscovered Charm of the Aegean
Leros is one of the Dodecanese’s best-kept secrets—an island of authentic charm, layered history, and relaxed coastal beauty. Often overlooked, it offers a more genuine glimpse into Greek island life, untouched by mass tourism. Scattered with sheltered bays and natural harbours, Leros is perfect for slow exploration. From the elegant waterfront of Agia Marina to the tranquil anchorages of Panteli and Vromolithos, every corner feels peaceful and inviting. Above it all sits the striking medieval castle of Pandeli, offering panoramic views across the island and sea. Leros carries a unique character shaped by its past, blending Italian architecture, naval history, and traditional Greek culture into one fascinating destination.
Samos – Lush, Wild & Timeless
Samos is one of the Aegean’s most diverse islands—where lush green mountains, crystal-clear waters, and deep history come together in a truly unique way. Rich in nature and culture, it offers a different energy to the typical Greek island experience. Explore picturesque harbours and traditional villages, wander through vineyards that produce the island’s famous sweet wine, and discover ancient landmarks like the Temple of Hera and the remarkable Tunnel of Eupalinos. Along the coast, hidden bays and long beaches provide perfect anchorages for swimming and relaxation. Samos feels alive and untamed—an island where you can move from mountain landscapes to turquoise seas in a single day, all while experiencing authentic Greek life.
Hosts
Crafting a Team together that combines Experience, Creativity, Energy who are experts in their specialty are the key factor to making your experience a next level success. Great Destinations, Great Moments are enhanced & memorable with a Great Team....
Yannis
Traveling the World with a Passion for Cultures, Destinations, Adventures & Culinary Delights our Award Winning Event & Entertainment Director provides a platform to share incredible experiences. Yannis is a natural storyteller who guides & enchants the guest the ultimate experience....
An Experienced Skipper having sailed in destinations around the planet.
Yannis is a Greek Australian & family origins are in the Dodecanese Islands so you are in great local experienced hands.
Languages: English, German, Greek, French & Italian
Schedule
We offer multiple Itineraries & Styles of Adventures
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Northern Dodecanese Itinerary
Set sail on a journey through the Northern Dodecanese, one of Greece’s most authentic and untouched sailing regions. This route blends remote island charm, crystal-clear waters, and rich cultural heritage, creating a truly immersive Aegean adventure.
Departing from Kos, your voyage begins with a magical moonlight sail to Samos, setting the tone for a week of exploration and freedom. Discover the laid-back beauty of Lipsi, where time slows down, and life revolves around simple pleasures—swimming in turquoise bays, wandering quiet villages, and enjoying fresh local cuisine.
Venture further off the beaten path to the hidden gems of Tiganakia Bay, Arki, and Marathi, where secluded anchorages and untouched landscapes offer some of the most pristine waters in the Aegean. These are the moments that define true sailing—quiet, raw, and unforgettable.
Continue to the spiritual and historic island of Patmos, home to the legendary Cave of the Apocalypse and a stunning hilltop monastery, before heading to Leros, a character-filled island rich in history, charm, and authentic Greek life.
Your journey flows into Kalymnos, famous for its sponge-diving heritage and dramatic landscapes, before returning to Kos for a final taste of island life and reflection on an extraordinary week at sea.
Southern Dodecanese Itinerary
Discover the soul of the Aegean on an unforgettable journey through the Southern Dodecanese, where dramatic coastlines, crystal-clear waters, and timeless Greek culture come together in perfect harmony. Sailing from Rhodos to Symi and beyond, this itinerary blends iconic destinations with hidden gems, offering a truly immersive island-hopping experience.
From the colourful neoclassical harbour of Symi to the turquoise serenity of Agia Emilianos, each stop reveals a new layer of beauty. Swim through the mystical Seal Cave, explore the spiritual calm of Panormitis Monastery, and anchor in breathtaking bays like St. George Bay, where towering cliffs meet electric blue waters.
This journey is not just about sailing—it’s about living the Greek island lifestyle. Enjoy long waterfront lunches, beach BBQs under the sun, and unforgettable evenings in charming harbours like Symi Yialos, including a signature dining experience at Nicki’s Cookhouse. Step back in time in Lindos, wander ancient pathways beneath the Acropolis, and dive into the iconic waters of Anthony Quinn Bay.
Your week concludes in the historic heart of Rhodos Old Town, where medieval streets, vibrant culture, and a sense of history provide the perfect finale to your adventure.
Accommodation
Catanoo, Lagoon 39
Base: Kos / Marina Kos, Greece Length: 39 ft Berths: 10 Cabins: 6 (4 +2) WC / Shower: 4
FROM$1,081.89 /pp
Thetis, Lagoon 450F
The Thetis is a 2020 Lagoon 450 F catamaran available for charter in Rhodes/Kos, Greece, accommodating up to 10-12 guests. This 4-cabin, 4-head vessel (plus crew cabins) features a flybridge, air conditioning, generator, solar panels, and electric toilets, making it a comfortable choice for sailing
FROM$1,322.31 /pp
Excess 11 Geva Mare X, Model 2022
8 guests / 4 cabins / 2+1 wc
FROM$1,021.78 /pp
Fountaine Pajot Elba 45 "Fugu II", Model 2025
The Fountaine Pajot Elba 45 Owner’s Version is a unique cruising catamaran with a spacious owner’s suite (cabin), two additional double cabins and generous living areas, combining light-filled interiors with excellent sailing performance.
FROM$2,103.68 /pp
Jeanneau Sun Odyssey 479 Aurelia, Model 2018
This 15-metre sailboat, available with four cabins, offers the perfect balance between performance, on-board comfort and ease of handling.
FROM$1,021.78 /pp
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You'll Be Staying Here
Share Cabin - Thetis Lagoon 450F
We have 4 x Matrimonial Cabins with Ensuite. The Accommodation is share setup.
Share Cabin - Fugu 2 Fountaine Pajot ELBA 45
We have 2 x Matrimonial Cabins with Ensuite. And an incredible large Owners Cabin. The Accommodation is share setup.
Share Cabin - Jeanneau Sun Odyssey 479 Aurelia, Model 2018
We have 4 x Matrimonial Cabins with Ensuite. The Accommodation is share setup.
Share Cabin - Excess 11 Geva Mare X, Model 2022
We have 4 x Matrimonial Cabins with Ensuite. The Accommodation is share setup.
Share Cabin - Cantoo Lagoon 39
We have 4 x Matrimonial Cabins with Ensuite. The Accommodation is share setup.