FROM € 890 /person
1 week 6 Islands 120 Nautical Miles


Welcome to sunniest corner of Greece, the South East Aegean! The “Dodecanese” is a group of 12 larger and 150+ smaller islands, only 25 of which are inhabited. Each one is rich in history and will captivate even the most well-travelled visitors. This is a unique journey to one of the most intriguing Greek destinations only known to local holidaymakers and experienced sailors. Hurry-up and explore this side of Greece before the rest of the world finds out!

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Kos is the birthplace of Hippocrates (460 BC), antiquity’s most noted physician and the father of medicine. Kos offers a great diversity of places for vacationers. Kos town, Kardamena and Kefalos, are very touristy and provide organized beaches, luxurious hotels, water sports and an intense nightlife. Other areas are almost secluded from mass tourism with naturism-friendly beaches and a more relaxed atmosphere. Take your time to explore before or after your sailing holiday!

We aim to be onboard by 5pm and sail the 1.5-hour passage to Pserimos, with a swim stop on the way. Pserimos is a tiny island of 80 inhabitants, a great one-night stop to experience life in one of the remotest corners of Greece. Feel free to engage with the friendly locals and talk about the life on the island, taste the catch of the day and enjoy the tranquillity of the beautiful surroundings.


Kalymnos is one of the most affluent islands in Greece. The island flourished due to sponge fishing. Kalymnos has a wild, rocky landscape and has recently become a famous as a rock-climbing destination hosting international festivals. The locals have preserved much of their traditional way of life. The island is rich in picturesque villages, where time stops, and days go by pleasantly and quietly. Getting around by car is the best way to explore and is highly recommended.

Pothia is the capital and the main port of Kalymnos. Take time to stroll around the impressive well-preserved mansions, the whitewashed bright coloured houses, the narrow alleys and old churches. Visit the Monastery of Agios Savvas to enjoy the incredible views over Pothia and the surrounding area.


Today’s destination is Leipsoi, a 4-5 hour sail from Kalymnos. We will stop en-route for a swim at the transparent azure waters of the tiny Makronisi. Leipsoi is a small island but there is so much to discover here. The village is surrounding the deep bay of the island’s harbour. Stroll around its cosy alleyways and blue-shuttered houses and visit the blue-domed church of “Panagia tou Harou” to enjoy the sunset views. The village is where the evening action happens. Enjoy the true island vibe and the smell of the charcoal grilled fish food that dominates the atmosphere. Try the catch of the day in the traditional tavernas owned by the fishermen and get a taste of the local wine and the excellent thyme honey.


It’s beach hopping day! Our trip includes several stops in the remote islets and the heavenly waters of the Leipsoi archipelago. Our first stop is Aspronisi, a tiny rock with a white pebbled beach. Next is the stunning Tiganakia, a hidden paradise of Arki island. Marathos island is a quick 15’ sail from there. Two families that live here manage the tavernas located on either side of the bay.

Their owners have laid mooring buoys so that sailors can enjoy their food and the beautiful surroundings. You will fall in love with the serene atmosphere and remote feeling of Arki and Marathos. If you are looking for a livelier place to spend the night, then the nearby Patmos is 1.5 hours away.


Patmos is a one-of-a-kind destination. The island has a rich history, intense spirituality and amazing natural beauty. Its impressive topography creates stunning views from almost every corner. Patmos has always been one of the most loved tourist destinations in Greece attracting visitors such as celebrities and royalty. All that while maintaining its genuine feel and charm.

Patmos is a significant Christian pilgrimage site. The Cave of the Apocalypse is where St. John the Theologian (St John the Divine) is said to have transcribed the Book of Revelations (Apocalypse). High above the Chora, a fortress-like 11th-century monastery dedicated to the Saint overlooks the whitewashed houses of the village. The Chora, the Monastery and the Cave of the Apocalypse are a Unesco World Heritage Site. Take your time for sightseeing and shopping, then follow the downhill foot path from the Chora to the harbour; the gorgeous views along the way are highly rewarding.


Leros has amazing landscapes, fishing villages, scenic tavernas, ancient ruins and an extraordinary modern history. It has only recently made it into the tourist radar. The coastal town of Agia Marina is the main settlement and our destination for tonight.

Take time to explore its abundant collection of whitewashed houses, neoclassical buildings and narrow streets. Atop Agia Marina sits the imposing medieval castle of the Knights of Saint John. Hiking there is the best way to enjoy some stunning views along the way.

If you are in for more exploration, driving around will get you to lovely seaside villages such as Alinda, Xirokambos and Partheni. Krifos is an isolated small cove with fantastic waters and a must-stop for a dive. Try scuba-diving if you are into it! The sea around Leros is rich in reefs and old shipwrecks.


The trip from Agia Marina to Kos lasts about 4 hours and there are several places on the way to stop for a swim. Xirokampos bay on Leros’ south coast, Akti bay at Kalymnos and Vathy bay in the east of Pserimos are all excellent spots. You should arrive in Kos no later than 8 pm; this will give you plenty of time to relax at the marina or venture off to the town, once more.


Time to say goodbye. Until next time, of course! Check-out is by 9am on the Saturday; if needed this can be done on Friday evening, according to your plans. There are several taxis available at the marina and the airport is an easy 30’ away.

  • Pserimos


  • Kalimnos


  • Leipsoi


  • Arkioi


  • Patmos


  • Leros


  • Kos



✔ 7 Days on Board Accommodation

✔ Professional Skipper with excellent local knowledge

✔ Yacht Insurance

✔ All port fees & taxes

✔ Towels, linen & end cleaning

✔ Dinghy with motor

✔ Snorkelling Equipment


● Boat Fuel (€150-250)

● Food & Drinks (€30-50 /person /day)

● Stand Up Paddle (€80/week)

● Car / Scooter / Bicycle Hire (€20-50/day)

● Cook on Board (€900 weekly)

● Entry to Museums & Archaeological sites

● Travel insurance

● Water Sports Activities


☺ Take a sightseeing tour around Kos old town

☺ Explore Kalymnos by car

☺ Scuba Dive in the shipwrecks of Leros

☺ Hike up to Patmos old town and visit the Cave of the Apocalypse

☺ Stay overnight at Marathos and try the local produce


  • 2-10 people per yacht.
  • No prior Sailing experience required.

Flexible on Dates? More than 10 people traveling? Have special requests? Get in Touch and we will be happy to add more destinations or create a custom experience for you!


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