Tour overview

The Dodecanese complex of islands is a paradise for sailing; it offers excellent weather conditions throughout all “summer” season (from May to October). With the meltemia (Northern) winds in our favor, we will sail from Kos to Rhodes, exploring four different islands on our way and countless hidden bays. Every island has a unique character, and our guide will be there to help you discover, mostly on foot, every magnificent corner of this full of light part of Greece.


  • Six days of sailing on the Aegean sea
  • Visit the volcano of Nisiros
  • Hike to Medieval castles
  • Coastal hikes to Tilos and Alimia
  • Countless chances to swim in turquoise waters
  • Visit cosmopolitan Symi
  • Wander in the Medieval town of Rhodes


Tour Summary


7 days

Period of Operation: April to October

Price / person:

May & October:

  • Min 4 participants on Armida or similar: 2,755€/person
  • Min 4 participants on Magic Irwin or similar: 3,700€/person

June & September:

  • Min 4 participants on Armida or similar: 2,755€/person
  • Min 4 participants on Magic Irwin or similar: 3,990€/person

for less or more participants please contact us

Participation requirements

Basic physical condition

Tour Details

Tour inclusions
  • Sailing boat (HANSE, 37 feet) –  Bathroom and Showering facilities (Hot and cold water) or MotorSailor (Magic Irwin) or similar
  • Professional Skippers and crew
  • All necessary port fees and fuel
  • Hikes (Days 3, 4, 5)
  • Town walks (not with licensed guides) (Days 2 and 6)
  • Cooking class (Day 5)
  • Breakfast daily (Days 1 to 7)
  • Lunches and drinks on board (Days 2, 3, 4, 5, 6)
  • Dinners in taverns (Days 2, 3, 4, 5, 6)
  • Local transfers to Kos, Nisiros and Rhodes
  • Two nights in boutique hotels (Kos and Rhodes)
  • Four nights on board in double cabins (3 in total)
  • Professional Trekking Hellas, English speaking Guide
Tour exclusions
  • Arrival to Kos & Departure from Rhodes
  • Personal expenses
  • Entrance fees to archaeological sites
  • Drinks during dinners
  • Optional gratuities to guide, skippers and crew


Arrival in Kos, settle in your hotel. Meeting at lobby with Trekking Hellas Guide for essential briefing before departure from the marina of Kos. Free time to wonder in the medieval castle of Kos, and through the streets of the new city.

After a nice breakfast, time to meet the crew that will welcome us on board on the sailing boat. After all the necessary information is given, it’s time to set off for our sailing adventure. First stop will be the magical island of Gyali, close to Nisiros. Both islands belong to the volcanic arch of the Aegean, so the land’s color is more than unique. Swimming and snorkeling time at Gyali’s crystal waters and then lunch on board. At the early afternoon we dock to Nisiros’ port, Palous, and we set off for our first walk – to the volcano! The experience of walking through a volcanic crater can be quite dramatic and breathtaking. At the evening, we will enjoy a dinner at a seaside tavern.

Sailing : 26 N.Miles (approx. 4 hours)

Walking : Within Stefanos’ crater (approx. 1 hour)

Next destination will be Tilos, an island that has been recently awarded as the most “green island” in the Mediterranean area, that its energy run entirely on wind and solar power. After some swimming stops in the Aegean sea and a wonderful lunch on board, we reach the main port of Tilos, the picturesque Livadia. Today’s hike combines all you have ever thought of Greece. Starting from Livadia, the trail leads us – following the coast line – to lovely beaches, including a red one – due to its soil. After reaching Lethra Beach, a green full of trees paradise, we begin the ascent towards Mikro Chorio – small village in Greek. Once a highly populated village, now a deserted one. Houses abandoned, narrow alleys, green yards and only inhabitants a few goats. During the summer months a bar operates here were customers can stroll around this one of a kind “ghost” village. Picturesque as it can be, we leave it behind, while starting the descend towards our starting point, Livadia.

Sailing: 20 N.Miles (approx. 3 hours)

Hiking : Km 7,5 Actual Hiking time 3 hours

Next on the program is the miniature island of Halki, that was once declared as the island of Peace and Friendship. Before though reaching its port, we set off for the deserted island of Alimia. We reach its first wide bay, where the main town once stood. This village was declared a protected settlement in 1978. There we disembark in order to hike through its untouched treasures. We wonder through forgotten trails, since the island is uninhabited since the Second World War In the Hellenistic times, Alimia was used as an anchorage and observatory for the Rhodian fleet. A tower was constructed that survives till today on the eastern side of the tallest peak of the island. Part of this Hellenistic tower was used for the construction of a Medieval Castle in 1475 by the Knights of Saint John, who had conquered Dodecanese that time. Once arrived to the second significant bay of the island, we have the chance to swim to its crystal clear waters, and then enjoy a lunch on board.

*The hike on Alimia island is considered as strenuous. If guide or guests decide not to follow, a visit to Alimia bay is suggested – lunch on board – and then a wonderful walk on Halki.

At the early afternoon, we sail to beautiful Halki. Its port resembles a postcard, with is colorful building’s facades that once belonged to rich sailors. Lovely dinner by the sea.

Sailing: 20 N.Miles (approx. 3 hours)

Hiking: Km 6 Actual Hiking time 2,5 hours

Early in the morning we sail to Symi, the most cosmopolitan but also remote island of the Dodecanese complex. On our way we stop to several bays to enjoy their emerald green colors, like Sesklia. After a lunch on board, we reach the port of Symi, early in the afternoon, and we walk till Pedi, a calm bay next to the town. At St Nicolas tavern it’s time to learn how to cook some of the famous Greek dishes that we have been enjoying all these days. At sunset time, we walk back to the port, while enjoying the picturesque views of Symi.

Sailing : 30 N.Miles (approx. 6 hours – stops included)

Hiking : Km 4, Actual hiking time 2 hours

Last day of our sailing adventure, and we sail to Rhodes, the largest and richest in history island of the Dodecanese. On our way we will have the chance to swim in some more bays, like St George Disalonas (Symi isl.) and enjoy a lunch on board, before reaching Mandraki port. The way in the port is totally unique due to the walls that surround the city and date from the medieval times. At afternoon time, we walk in the city’s walls to enter the medieval town that is declared an UNESCO Heritage Monument. We will surely feel the mysterious atmosphere of the castle and wonder through its narrow alleys. Farewell dinner in the old town and check in in our hotel.

Sailing : 24 N.Miles (approx. 3,5 hours)

Walking : Km 2, Actual hiking time 1,5 hours

Departure day. Transfer to airport (or extension of the trip).


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