Sailing in the Dodecanese islands


Hidden in the very South- East corner of Greece and hugged by the Turkish coast the Dodecanese complex of islands wait to be discovered. Their strategic position, in the middle of the most important East-West trade routes, made many seafarer powers fight for dominance. Thus, today there are traces of everyone from Greeks and Romans to crusading medieval knights, and from Byzantine and Ottoman rulers to 20th-century Italian bureaucrats. The result is a diverse group of islands with fascinating archaeological sites, ancient walking trails , medieval castles, and charming whitewashed villages.On top of that, the Dodecanese complex encompasses varied landscapes of immense beauty, unforgettable coastal scenery and tranquil, turquoise waters providing the ideal setting for our style of guided walking tour: a mix of glorious land and seascapes, little-used walking trails, friendly people, wonderful cuisine, and the luxury and romance of traveling by private yacht. And what a yacht! We have a gorgeous 32-meter (103 feet), all-wood, two-mast gullet with a crew of four to cater your every need. This trip offers the perfect balance between relaxation and activity, as we will have plenty of time to relax on board, enjoy the warm waters of the Aegean and explore the islands of Kos, Nisyros, Chalki, Tilos, Symi and Rhodes. All you need to do is lay back on the cushioned rear deck and enjoy the beauty of the Greek archipelago!


Arrive in Kos, and meet the group at Akti’s hotel reception. This is the second largest island of the Dodecanese after Rhodes, with a rich history reflected in its architecture and historic monuments. The harbor is guarded by the imposing castle of the Knights of St. John, in the town 17th century Ottoman mosques stand next to austere Italian public buildings, built during the fascist period while extensive Hellenistic and Roman remains lay amongst public gardens. After a short walking tour in the city’s historical center, we will have lunch and set out for a 3-hour sunset passage to the island of Nisyros. Tonight, we moor in the port of Mandraki and dine at a wonderful local taverna in Nisyros town.

Overnight in Nisyros
Lunch and dinner included
Cruise time:
Kos to Nisyros 3 hr

The tiny round island of Nisyros is Greece’s youngest volcano and it has only four villages. Mandraki and Pali are on the coast, while Emporeio and Nikia are perched on the edge of the volcano’s crater. In the morning, we are transferred to the floor of the 4-km wide caldera to walk inside Stefanos crater. Such visits are a once-in-a-lifetime opportunity, given that craters are rarely accessible and feels like you are walking on the moon! We depart on foot to climb out of the caldera, up to the whitewashed village of Nikia. This short but beautiful hike will reward us with extraordinary views. We will enjoy a cool drink and lunch in the picturesque square before we head back to Mandraki port where we will rejoin the boat for our 3-hour sunset to the island of Tilos.

Overnight in Tilos
Breakfast lunch and dinner included
Hiking distance:
3 km / Hiking Duration: 2 hr
Sailing distance:
Nisyros to Tilos 3 hr

Enjoy a Mediterranean breakfast that includes fresh fruits, olives and some of the best yogurt in the world and disembark for a hike to one of the smallest and least inhabited islands in the country. We walk across the coast for stunning views of the Aegean Sea. On first sight, the island seems to be bare and barren but as we follow the old stone trail to the inland, it soon becomes apparent that the dramatic landscape is less hostile than expected. We hike amongst ancient terraces of olive  and carob trees. The footpath winds uphill to the abandoned medieval settlement of Mikro Chorio. Today out of the 220 houses of the village, only the ruins of impressive stone houses can be seen. Round threshing circles, olive pressing stones and cisterns stand witness to Tilos’ intense agricultural past activity. We loop back down to Tilos town to rejoin our yacht. It is time to swim and enjoy Greece’s azure waters! In late afternoon opt for the optional hike to the ancient settlement of Gera or stay on board for more swimming opportunities. Tonight, we moor in a quiet cove to dine under the starry night sky.

Overnight in Tilos
Breakfast lunch and dinner included
Hiking distance:
7 km / Hiking Duration: 3 hr
Optional afternoon hike: 5 km / Hiking Duration 2 hr

Forget Tilo’s cubic whitewashed houses, the town of Chalki  is brightly colored with 19th-c. Neoclassical houses and ceramic-tiled roofs. Some of these houses are right on water, and residents dive from their front patios right into the port’s crystal-clear waters. We walk through the town and then climb up to the imposing ruins of a castle built by the Knights of Saint John, once an important bastion during the Crusades. From this vantage point you can look over to the massive bulk of the island of Rhodes, and you may also catch a glimpse of our yacht as it cruises around to a quiet cove to pick us up after our descent.

Overnight in Chalki
Breakfast lunch and dinner included
Hiking distance:
6 km  / Hiking Duration: 3 hr
Sailing distance:
Tilos to Chalki 2 hr 30 min

Have a refreshing morning swim, and then we will set “sail” once again to the island of Symi for today’s spectacular hike which is the most challenging but perhaps the most rewarding one in our trip. Our dinghy will take us on the beach to start our hike which initially ascends steeply on a narrow cliff. Soon we reach at the top and the sea views are breathtaking. Symi is the first island we visit which has a forest. So, as we traverse across the island towards the colorful town of Symi the landscape alternates between stark limestone mountains, the deep blue sea and the green of the cypress tree forest. Our flagstone path gradually descends taking us to the town. The first sight of Gialos harbor is unforgettable.
Two-story, pastel-colored neoclassical houses, with tall windows and doors are built amphitheatrically on the slopes rising on all sides. And above all, today we are having a fabulous seafood lunch overlooking at the sea. In the afternoon you are free to wander around and do some shopping at the numerous boutiques in town since we’ll be moored in the port.

Overnight in Symi
Breakfast lunch and dinner included
Hiking distance:
6 km / Hiking Duration: 3 hr
Sailing distance:
Chalki to Symi 3 hr

Today we will meet a local family for our cooking class, so step back in time and feel the warmth of Greek hospitality in all its generosity. Our hosts Irene and her mother Katina are sharing with us their family’s cooking secrets and even more importantly their family’s history. Members of one of the oldest families on Symi, they were involved in sponge diving and shipping, which greatly benefited the island. Today, we visit their “vacation” house at serene Emporios bay, and we learn how to make tzatziki sauce, stuffed tomatoes, and spinach pie all baked in a wood oven.
We walk back to Symi town for a last shopping opportunity before getting picked up by our gullet. It is time for a swim and we circumnavigate the island to reach the spectacular Ai-Giorgis beach where we spent the night.

Overnight in Symi
Breakfast lunch and dinner included
Hiking distance:
2 km / Hiking Duration: 1 hr

A short morning cruise takes us to the starting point of today’s hike. We walk through a fragrant pine forest to the Archangel Michael Monastery on the southern end of the island. Built in the 15th century, the monastery overlooks the bay in a truly magical setting surrounded by green hills. Visit the historical church which stands as one of the most important pilgrimage destinations of the country and hop on the gullet for a last swim and lunch.
Early in the afternoon, we will cruise to the island of Rhodes which is the 4th largest in Greece and the historical capital of the Dodecanese where Byzantines, Venetians, Turks and Greeks all left something to remember them. The  Medieval town of Rhodos, declared as UNESCO World Heritage Site, is one of the biggest and best preserved medieval settlements of Europe. We explore the Old Town and we dine in a local taverna for one last farewell meal with our shipmates.

Overnight in Rhodes
Breakfast lunch and dinner included
Hiking distance:
2.5 km / Hiking Duration: 1 hr
Sailing distance:

Symi to Rhodes 3 hr

We have to disembark by 8 a.m. this morning, so you can schedule onward travel any time after that.

Breakfast included







  • Seven nights accommodation on a 32-meter, all-wood, two-masted gulet with a crew of four to look after every need
  • All costs related to the boat charter and operation, such as fuel, port fees, and custom fees
  • All transportation during the trip
  • All activities mentioned in the program
  • Entrance fees to the Nisyros volcano
  • Services of a guide throughout the tour
  • Transport and handling of one reasonably sized suitcase and one carry-on per person


  • International air fare
  • Transfer to and from the airport/port
  • Medical expenses
  • Travel or emergency evacuation insurance
  • Gratuities for leader/guide or driver
  • Alcoholic beverages and meals other than outlined in itinerary
  • Extra boat provisions (beer, wine, soft drinks etc)
  • Visas if needed
  • Other items of a personal nature
  • Anything not mentioned in above program


  • Breakfast
  • Lunches and dinners as indicated in the itinerary


We are constantly updating our unique itineraries based on new information and experiences available. The walks, accommodations, and visits listed may be adjusted. The itineraries presented are subject to modification and change by Tripin Adventures. We reserve the right, without penalty, to make changes in the published itinerary whenever, in our judgment, conditions warrant, or if we deem it necessary for the comfort, convenience, or safety of participants, anything not mentioned in above program.


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