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Tour overview

Sailing & Hiking the Dodecanese Islands is a 7-day Sailing and Hiking Tour in the Dodecanese Islands – a true paradise for enjoying life on the ocean irresistibly combined with hiking!

The Dodecanese Islands are an ideal sailing destination as they offer excellent weather conditions throughout the “summer” season (from May to October). So with the meltemia (Northern winds) in our favour, we sail from Kos to Rhodes, exploring four different islands and countless secluded bays on our way. Every island has a unique character and our guide is there to help you make the most of exploring this beautifully unique area of Greece.

Our Sailing and Hiking Tour starts on the island of Kos. Here we meet our friendly crew before we embark on our sailing trip. Our first stop is the volcanic island of Nisiros. We will have plenty of time to swim and in the afternoon we will hike to Nisiros’ volcanic crater. Our next destination is Tilos, unspoiled and truly authentic! We explore the islands lovely beaches, abandoned villages and encounter the island’s goat population which by far outnumbers its human population! Our journey continues to colourful and laid-back Halki . We also enjoy a stop on the deserted island of Alimia and the last tiny island we set anchor on during our voyage is vibrant Symi. A petite and yet cosmopolitan holiday destination. Our trip ends on Rhodes, renowned for its UNESCO World Heritage Medieval Town among many other things.

Highlights of Sailing & Hiking The Dodecanese Islands:

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

Trekking Hellas offers a variety of activities and tours on Rhodes and the Dodecanese Islands and indeed all over Greece that can be added to your itinerary, which you can customize according to your own tastes. You can extend your stay on Rhodes by staying in charming lodging in the medieval town and actively explore the island with our day tours such as  Mt. Akramitis hikesea kayaking, visiting  the Lindian masterpiece which is the Temple of Athena in Lindos, either with Hiking Lindos or Kayaking Lindos or for food lovers we recommend our Tastes of Rhodes tour.


Tour Summary


7 days

Period of Operation: May & June  / September & 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 fitness

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 2 to 7)
  • Lunches and drinks on board (Days 2, 3, 4, 5, 6)
  • Dinners in tavernas (Days 2, 3, 4, 5, 6)
  • Local transfers in 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 into your hotel. Meeting in lobby with Trekking Hellas Guide for essential briefing before departure from the marina of Kos. Free time to wander around the medieval castle of Kos and through the streets of the new town.

After a tasty breakfast to set us up for the day, it’s time to meet the crew who warmly welcome us on board the sailing boat and our home for the next few days. After they give us all the information we need to know, it’s time to set off for day one of our exciting adventure – Sailing & Hiking the Dodecanese Islands. First stop on our Sailing and Hiking Tour is the magical island of Gyali, close to Nisiros. Both islands belong to the volcanic arch of the Aegean, so the colour of the land there is without a doubt unique. We enjoy some time swimming and snorkeling in Gyali’s crystal clear waters and then enjoy a reviving lunch on board. In the early afternoon we dock in the port of Nisiros, Paloi, and we set off for our first walk – to the volcano! The experience of walking through a volcanic crater is enough to take your breath away and can only be described as a one-of-a-kind experience. In the evening, we enjoy a well-deserved delicious dinner at a seaside taverna.

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

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

Our next destination on Sailing & Hiking the Dodecanese Islands is Tilos, an island that has recently been given an award and the title of the Environmentally Greenest Island in the Mediterranean as its energy derives entirely from solar and wind power. After some swimming stops in the middle of the Aegean Sea and a wonderful refreshing lunch on board, we reach the main port of Tilos, picturesque Livadia. Today’s hike combines all you have ever thought of Greece. Starting from Livadia, the trail leads us along the coastline to lovely beaches, including a red beach – due to the colour of its sand. Thereafter, having reached Lethra Beach, a green tree-lined paradise, we begin the ascent towards Mikro Chorio (meaning small village in Greek). Once a densely populated village, it is now deserted. Houses have been abandoned and they remain along with the narrow alleys, green courtyards and its few present inhabitants – goats. During the summer months a bar operates here from which customers can stroll around this unique “ghost” village. Picturesque as it may be, we are forced to leave it behind, in order to start our descent back towards our starting point, Livadia.

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

Hiking: 7.5 Km (Actual Hiking time 3 hours)

Day 4 of our Sailing and Hiking Tour takes us to the quaint island of Halki. Once declared the Island of Peace and Friendship. Before reaching its port, however, 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 among its untouched treasures. We find ourselves wandering along forgotten trails as the island has been uninhabited since the Second World War. In Hellenistic times, Alimia was used as a point of anchorage and an observation point for the Rhodian fleet. At the time a tower was constructed on the highest peak of the island, on its eastern side and still survives to this day. 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 The Dodecanese Islands in that era. Once we arrive at the second significant bay of the island, we have the chance to swim in its crystal clear blue waters, and then enjoy lunch on board our boat.

*The hike on Alimia Island is considered strenuous. If you or our guide decide not to go ahead with it for any reason, a visit to Alimia bay is an alternative, followed by lunch on board and then a wonderful walk on Halki.  

In the early afternoon, we sail on to beautiful Halki. Its port resembles a postcard, with the colourful facades of its building, which once belonged to rich sailors. We finish off day 4 of our adventure with a lovely dinner by the sea.

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

Hiking: 6 Km (Actual Hiking time 2.5 hours)

Today we start early in the morning on Sailing & Hiking the Dodecanese Islands. Our destination? Symi, the most cosmopolitan but also most remote island of the Dodecanese Islands. On our way we stop at several bays to enjoy the emerald green colours of the water, an example being Sesklia. Thereafter, follows a revitalizing lunch on board and then we reach the port of Symi, early in the afternoon. Once anchored in Symi town, we walk to Pedi, a calm bay near the town. At St Nicolas taverna it’s time to learn how to cook some of the famous Greek dishes that we have been enjoying throughout our trip so far over the last few days. At sunset, we walk back to the port, enjoying picturesque views of Symi on the way.

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

Hiking: 4 Km (Actual hiking time 2 hours)

On the last day of our Sailing and Hiking Tour, we sail to Rhodes. Rhodes is the largest island of the Dodecanese and boasts the richest history. On our way we will have the opportunity to swim in some more bays, like St George Disalonas (on Symi Island) and enjoy a delicious lunch on board, before reaching Mandraki harbour. Entering the harbour is a truly unique experience due to views of the walls that surround the Old Town and which date from medieval times. During the afternoon, we walk inside the city’s walls to explore this medieval town which has been declared a UNESCO World Heritage Monument. We take in the mysterious atmosphere of the Old Medieval Town and its imposing castle and wander through its narrow alleys before enjoying a farewell dinner there and checking into our hotel.

Sailing: 24 N.Miles (approx. 3.5 hours)

Walking: 2 Km (Actual walking time 1.5 hours)

Departure day. Unless you have decided to extend your trip further, today you will be transferred safely to the airport. We are sure you will have enjoyed it as much as we have enjoyed hosting your one-of-a-kind adventure. Sad to see you go we are sure you will be back to join us soon on another trip of a lifetime!


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