Walking & Cruising The Dodecanese in September - An Archaeological & Cultural Sailing Adventure


Walking & Cruising The Dodecanese in September - An Archaeological & Cultural Sailing Adventure



1 month ago


8 Days/7 Nights


28th September 2019 - 5th October 2019


GBP 2,845.00 per person


Sep 26, 2019
Walking & Cruising The Dodecanese in September - An Archaeological & Cultural Sailing Adventure
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The islands of the North Dodecanese are the emergent tips of a sub-sea mountain range that stretches across the Aegean sea. Each one has a subtly different feel from its neighbours, a variety expressed in their cuisines and their architecture, but above all in their landscapes and vivid histories. Viewing them from the deck of your gulet as you cruise between these islands with a perfectly chilled glass of wine in hand, it’s easy to marvel at the geological forces that shaped them; but, to appreciate their true grandeur, walk their undulating valleys, over their rugged hills, and rise to the very tops of their breathtaking summits.

This trip brings together the best experiences this area can offer: the elegant and laid-back pleasure of a gulet cruise, the thrill of walking through an array of wonderful landscapes, the region’s fascinating multi-faceted history, the joy of swimming in the blue waters of the Aegean and the delights of fresh local cuisine, enjoyed both on and off the gulet. It is a unique opportunity to explore these island landscapes on foot and to discover superb archaeological sites far from the beaten track.

The combination of the islands you will visit and the walks we have prepared on each will offer you a panoramic insight – literally and metaphorically – into a region of enormous historical depth, and one that conceals a great wealth of hidden beauties rarely noticed by visitors. Accompanied by our expert guides, you will gain an intimate understanding of each island, its landscape, its past and present, and its individual character.

On Kalymnos, a long and peaceful valley, unfolds an archaeological timeline from Classical Greece to the Byzantine era and beyond, as one site after another lines up along the border between lush agricultural land and the island’s characteristically rocky uplands. On Leros, a seemingly serene mountaintop holds a fascinating array of mementos of the island’s turbulent role in the Second World War. On tiny, rarely-visited Telendos, we walk a route through a remarkable collection of Byzantine monuments, including the wild clifftop stronghold of Agios Konstantinos, a place that is truly out of this world. In Kos, we will explore the hidden remains of a barely-excavated ancient Greek city and ascend to the pinnacle of a soaring crusader castle that commands fantastic views of the neighbouring islands. Nisyros sees us walk the bucolically fertile slopes of an enormous volcanic caldera and enter a spectacularly-located ancient Greek fortress. Step by step and story by story, this remarkable voyage will unfold the layers of history, combining into an unforgettable experience of riveting tales, stupendous vistas and the sheer natural beauty of each island.


Rate is per person, based on double occupancy. The single supplement fee is £695 per person.


Day 1:
Kos, Dodecanese, Greece

Your gulet awaits you in the ancient and modern port of Kos, 45 minutes from the airport. Welcome dinner aboard.

Day 2:
Kalymnos, Dodecanese, Greece

We cruise north to the rocky island of Kalymnos, and take a lovely walk through the long valley of Vathy in the afternoon, visiting a series of fascinating ancient sites ranging from an imposing ancient Greek fortress to an array of beautiful early basilica churches and an extensive necropolis.

Day 3:
Leros, Dodecanese, Greece

We continue northwards to Leros, where we will hike to the top of Mt Patela, an important military installation in the Second World War, riddled with mysterious tunnels built by Italian troops and crowned by the “acoustic mirror”, a near-unique leftover of 1930s technology.

Day 4:
Kos, Dodecanese, Greece

South to central Kos, where in the afternoon we make our way to the uplands of the island, to the impressive eyrie that is the crusader castle of Palaio Pili. The panoramic view from the ramparts of the castle encompasses much of the seas and islands we have travelled in the previous days, a spectacular reminder.

Days 5:
Nisyros, Dodecanese, Greece

A morning crossing brings us to Mandraki, the port of Nisyros, the whole island being a mostly dormant volcano. We hike the slopes of the vast caldera that forms the interior of the island, where we will discover the timeless connection between the island’s fiery geological inheritance, its fertile volcanic soils, and the lives that humans have made here for millennia.

Day 6:
Kos, Dodecanese, Greece

Heading north in the morning, we drop anchor off the Kefalos Peninsula in Western Kos. Here, a leisurely hike through a peaceful agricultural landscape gradually reveals a series of tombs, terraces, walls, churches, temples and a theatre: the remains of the city of Astypalaia, still almost entirely unexplored. In the afternoon, we cruise to the Bay of Emborio in Western Kalymnos, where we anchor for the night.

Day 7:
Kalymnos, Dodecanese, Greece

Telendos, a limestone outcrop rising from the Aegean Sea, nestled into the great western gulf of Kalymnos. Scattered around the little port, we will explore a huge basilica church and a series of well-preserved Byzantine tombs. After crossing to Kalymnos itself, we explore that island’s medieval Chora, a mighty fortification atop a steep-sided plateau, where crumbling ramparts and a plethora of chapels stand witness to a turbulent past. In the afternoon, we return to Bodrum, where we will enjoy a farewell dinner moored in the historic harbour.

Day 8: Departure
Kos, Dodecanese, Greece

Departures from Bodrum harbour to Bodrum airport.


  • Full Board Accommodations on the Gulet
  • Airport Transfers on First and Last Day of Tour
  • All Crew Services on Gulet
  • Entrance Fees and Tips on Land
  • Excursions with Expert Guides
  • WiFi on our Scheduled Gulet Cruises (when coverage permits)

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