Hiking South Dodecanese

8 days Sailing & Hiking from Kos to Rhodes, Greece


Navigate through some of the most magical walking paths to find charming remote villages and ruins. Enjoy the view alongside spectacular ridges, around breathtaking natural sites and over a Volcano Island. Make your way across the land for an afternoon rendezvous with your yacht and a refreshing dip in some of the clearest waters Greece has to offer.


The Highlights

  • Volcano Island of Nisyros, where you will walk the crater of this active mythical giant in the morning and laze about in the quant villages in the afternoon enjoying the abundant local cuisine

  • Explore castles, fortresses and towers throughout the journey, dating from medieval to ancient times. All with their own story

  • Medieval town of Rhodes, where modern Greece meets the not too distant past throughout every day life

  • Picturesque south-coast of Chalki with its clear waters and hidden cave complexes

  • Enjoy the experience and rejuvenation of natural thermal springs while nestled in nature


The Details

Vessel Type_ Standard Sailing Monohull

Capacity_ up to 8 travellers

Services_ Skipper + Hike Leader


We have planned this trip for people who love hiking and take great delight in exploring the natural surroundings of the places they visit. Covering around 140NM, the traveler will visit Kos, Nisyros, Tilos, Symi, Halki, and Rhodes to be captivated by their unique history and natural beauty. The eye-catching environment of the Dodecanese abounds with walking paths of moderate difficulty and varying route lengths suitable for all levels.

This trip operates with a minimum crew of 2 including a fully licensed professional Skipper and a Hike Leader to offer guidance and safety while hiking.


Day by Day

Day 1 Kos to Nisyros

Early this morning, you will meet your crew at Kos Marina to prepare provisions, discuss the details of the trip and the hiking plan that befits your mood and competences. Your hiking experience begins in Kos with a scenic route leading to the summit of Mountain Dikaios with an approximate height of 850m. For the biggest part of this track, you will enjoy a picturesque view an enrapturing introduction to the Aegean scenery. You will meet the boat in the beach of Therma to enjoy a great swim and repose before setting sail for the island of Nisyros, where you will anchor for the night and enjoy the first dinner under the stars.

Optional: Cycling, Climbing, Kite-surfing, Wind-surfing, Flyboarding

Sail for approximately 24NM

Night Anchorage: Nisyros Paloi port

Day 2 Nisyros

After a morning swim and hearty breakfast, you will take a walk to the capital of the island, Mandraki, with its uphill paths and the medieval castle built in the 14h century by the Catholic military order of the Knights of Saint John of Jerusalem. Today’s hiking exploration has a very spectacular destination, the crater of this volcano island which you will reach after a 2-hour hike on the caldera slopes forming a ring around the active crater. Admire the uncommon vegetation and the traditional farmhouses ("spiladia") built on the concavity of the hills. The fittest amongst you can walk to the summit of the crater, then meet the rest of the group and follow the walking path which leads to the nearby traditional villages, where you will laze about and enjoy the abundant local cuisine. Your hiking tour will end once you reach the south of the island where the boat will wait for you for an afternoon swim and a relaxing sunset on-board.

Optional: Cultural Tour, Local Food & Wine tasting

Sail for approximately 9NM

Night Anchorage: secluded cove

Day 3 Tilos

Enjoy an early swim and breakfast before we set sail to our next destination, the island of Tilos, a place with much to see and learn. We will moor at Agios Antonios Beach on the north side of the island, wherefrom a bus will take you to the capital of the island, Megalo Horio, to walk around and visit the Paleontological Museum. There the findings from the excavations of the Charkadio Cave are exhibited, including the famous fossils of the dwarf elephants to which the species name "Elephas tiliensis" has been assigned. Your next stop will be the Saint Panteleimon monastery, surrounded by cypresses and plane trees, where your 3-hour hiking of today will begin. Follow a scenic track stretching to the western side of the island and you will end up to the sequestered Limenari Beach for a refreshing swim and lunch on-deck. Afternoon sail to the most beautiful beach of the island, Tholos beach, where we will moor for the night.

Sail for approximately 23NM

Night Anchorage: Tholos beach

Day 4 Halki

This day is you to Halki, an island with splendid beaches along a ravishing coastline dotted with hidden caves, small fjords, and steep rocky sites. We’ll sail to discover those sceneries and swim in the clear waters of the island arriving in the afternoon to the picturesque port of Halki, Nimporio, where you will have the chance to stroll around or visit the medieval castle of the island.

Sail for approximately 20NM

Night Anchorage: Nimporio port

Day 5 Alimia

Get back to your hiking mode today as we will sail early in the morning to the nearby Alimia, a small island, uninhabited since WWII. The remnants of a village settlement form an ideal setting for exploration, while after an 1-hour hiking you’ll reach the top of the mountainous island where another medieval castle adds a special touch and offers a majestic view to Halki and Rhodes. Night sail to the island of Symi and moor on Agios Vasilios bay for a relaxed, summer night.

Sail for approximately 25NM

Night Anchorage: Agios Vasilios bay

Day 6 > Symi

Enjoy your breakfast and the first swim on this lovely spot wherefrom you will later choose between two hiking trails, either to the capital of the island or to Agios Emilianos beach. After hiking, meet your boat in the main port of the island, where you can mingle with the locals, taste traditional dishes and spend the night.

Optional: Scuba-diving

Sail for approximately 15NM

Night Anchorage: Symi port

Day 7 Symi to Rhodes

Morning hiking to Agia Marina, a beautiful beach where the boat will wait for you to enjoy your swim before you set sail to the stunning Agios Georgios beach for another round of plunges off the boat’s deck and lunch. Evening sail to the island of Rhodes. Get a first taste of this magnificent island’s nightlife and cultural flavor.

Optional: Scuba-diving, Sea-kayaking

Sail for approximately 25NM

Night Anchorage: Mandraki port

Day 8 Rhodes

Early wake up for breakfast, final on-board selfies and disembarkation.