Sailing & Hiking The Dodecanese Islands

Sailing & Hiking The Dodecanese Islands

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!

May & June / September & October
Private Departures only
7 days
Sailing & Hiking The Dodecanese Islands
Price from €3650


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 Nisyros. We will have plenty of time to swim and in the afternoon we will hike to Nisyros’ 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.

Day 1
Arrival in Kos
Day 2
Kos to Nisyros
Day 3
Nisyros to Tilos
Day 4
Tilos to Halki
Day 5
Halki to Symi
Day 6
Symi to Rhodes
Day 7

Activities / Schedule

Arrival in Kos

Arrival in Kos, settle into your hotel. Meeting in lobby with Trekking Hellas trip leader for essential briefing before departure from the marina of Kos. Walk to dinner location with your trip leader passing from the medieval castle of Kos and through the streets of the new town.

Kos to Nisyros

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 Nisyros. 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 Nisyros, 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, free time for dinner or stargazing on board!

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

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

Nisyros to Tilos

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.

In the evening, free time for dinner or easy wander at Livadia bay!

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

Hiking: 7.5 Km (Actual Hiking time 3 hours)

Tilos to Halki

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. 

In the evening, free time for dinner at Halki seaside promenade!

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

Hiking: 6 Km (Actual Hiking time 2.5 hours)

Halki to Symi

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 Seskli. 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)

Symi to Rhodes

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!

Important Info

In a glance

euro (€)
UTC+02:00 (EET)


  • Six days of sailing in the Aegean sea
  • Visit the volcano of Nisyros
  • 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

Prices - Sailing Boat Armida (or Similar)

May & June / September & October:

  • Private Departures for 4 participants on Armida or similar: 3650€/person

We can arrange for a second similar sailing boat for bigger groups - please contact us!


General Information

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.


Please consider taking along the following items on your trip. This is not a fixed list, but more of a guideline, so feel free to add and remove items as you see fit.
Greece has a temperate climate. Base your clothing on the “layering system”, if it is hot you can “peel off” layers quickly, if it is cooler and windy you can quickly “dress up”.


  • Duffel bag or rolling luggage
  • Day pack to carry camera, water bottle and snacks etc.
  • Luggage locks and tags


  • Mid-weight polar fleece sweater
  • Rain jacket and rain pants, or poncho


  • Hiking shorts
  • Casual clothing made of light-weight fabrics
  • T-shirts
  • Long-sleeve shirt
  • Hiking pants, loose and easy to move in
  • Underwear
  • Swimsuit

Clothing Accessories

  • Sun hat or baseball cap


  • Lightweight and supportive hiking boots, broken-in with good ankle support
  • Beach sandals
  • Casual, comfortable shoes for evening


  • Sunscreen and lip protection
  • Sunglasses and retainer strap
  • Beach towel

Optional Accessories

  • Security pouch or money belt
  • Trekking poles or walking staff
  • Camera, memory and batteries
  • Reading and writing materials
  • Watch with alarm or travel alarm
  • Travel pillow
  • Motion sickness remedies
  • Personal first-aid kit
  • Insect repellent (lowrisk)
  • Electrical adapter plug/converter

The lighter you travel, the easier you travel. Use your best judgment and pack as lightly as possible. You will appreciate light luggage towards the end of your trip.

Sailing & Hiking The Dodecanese Islands

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!

Price from €3650



What should I bring with me?

  • What is listed above in Equipment section

What's the meeting point & time?

Meeting Point: Kos Airport or Port

Time: Ideally before 18.00.

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