HoliSail

The Dodecanese

Kos

The Dodecanese island group is a dream destination for history lovers, sailors, and food enthusiasts. With a mix of Greek, Byzantine, Ottoman, and Italian influences, it captivates visitors with its medieval Old Town, vibrant nightlife, and golden beaches. The cuisine blends Greek and Middle Eastern flavors, with specialties like stuffed squid, local cheeses, and baklava.
Explore Rhodes, where medieval castles meet golden beaches and vibrant nightlife, or wander through the ancient ruins of Kos. Discover the neoclassical charm of Symi and Halki, where serene harbors and crystal-clear waters create the ultimate escape. Whether you’re drawn to the energy of historic towns or the tranquility of secluded bays, this journey promises an extraordinary blend of adventure, relaxation, and timeless Greek beauty.

7 Days Plan

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from € 550 /person

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Day 1

Our adventure begins on the island of Kos, where we board our boat and go through a short briefing before setting sail toward our first destination—the charming island of Pserimos. With its crystal-clear waters and tranquil atmosphere, it’s the perfect place to ease into the rhythm of the sea. As the sun sets, we’ll enjoy our first evening under the stars, immersed in the serene beauty of the Aegean.

  • Note: Car parking in the marina is free and safe.

Your mornings will soon become a cherished ritual—waking up slowly, savoring a fresh cup of coffee with breakfast, and starting the day with a refreshing dip in the sea.

As we set sail, stretch out on deck, soak in the warm sun, and let the endless blue surround you. Our next stop is one of Kalymnos’ stunning bays, where dramatic cliffs, crystal-clear waters, and a laid-back charm create the perfect setting to drop anchor, swim, and unwind in nature’s beauty.

On day three, whether you decide to explore a charming island town or unwind in a secluded bay, Leipsoi will be waiting to welcome you. A hidden gem of the Dodecanese, this island invites you to slow down and embrace the simple beauty of the Aegean.

Stroll through its peaceful streets, savor fresh seafood at a seaside taverna, or take a dip in its pristine turquoise waters—whatever you choose, Leipsoi will not disappoint.

Our journey continues to Arki, a tiny, untouched island where nature reigns supreme. With only a handful of inhabitants and no crowds, it’s the perfect escape from the noise of modern life.

Here, time slows down. We’ll anchor in one of Arki’s stunning bays, where the crystal-clear waters and serene surroundings feel like a hidden paradise. Spend the day swimming, sunbathing, or simply soaking in the peaceful charm of this remote island gem.

On day five, we set sail for Patmos, the legendary “Island of the Apocalypse.” After a leisurely cruise, we’ll dock in one of its marinas and prepare for a land excursion to Chora, the island’s historic heart. Home to the Monastery of St. John, Patmos captivates visitors with its charming streets, breathtaking views, and soothing island atmosphere.
As we explore Chora, you’ll wander through whitewashed alleys, uncover hidden courtyards, and soak in the island’s unique energy. Whether you’re drawn to its rich history, stunning scenery, or simply wish to enjoy a laid-back afternoon, Patmos has something truly special to offer.

Today, we slowly begin our journey back, setting sail for the enchanting island of Leros. A few days before, we admired its beauty from afar—now, we have the chance to truly experience it.
With its hidden bays, charming villages, and a unique blend of history and nature, Leros invites you to explore it at your own pace. Wander through its quaint streets, unwind on its peaceful beaches, or savor a delicious meal at a seaside taverna—a perfect balance of tranquility and island charm awaits.

Today, we set sail back to Kos, enjoying a smooth and easy journey as we reflect on the incredible moments we’ve shared. With the sea breeze in our hair and the endless blue stretching before us, it’s the perfect time to savor the last hours of our adventure.

Once we arrive, we’ll gather for a final dinner, reminiscing about the unforgettable experiences of the past days. After one last night on board, saying goodbye won’t be easy—but we part ways knowing that another adventure is always on the horizon.

 

Disclaimer: The proposed travel plans are intended for informational purposes. Depending on weather conditions and other unforeseeable factors, they may be adjusted, based on necessity and your personal preferences, in consultation with our skipper.

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