Sailing & Hiking from Kos to Rhodes

After checking out from your accommodation, at 10.00, 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)

Lunch on board / Dinner on your own

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)

Lunch on board / Dinner on your own

After breakfast, set sail toward Symi, stopping at the secluded Agios Emilianos Bay for a refreshing swim in crystal-clear waters and a light lunch on board. From here, your hiking adventure begins. Follow scenic trails through a fragrant pine forest, alive with aromatic herbs and dotted with small chapels, as you make your way toward the historic Agios Roukouniotis Monastery, a fortified complex dating back to the 15th century.

Along the route, pass St. John Church, perched above the turquoise waters and offering stunning views of the distant mountains — a perfect spot to pause, reflect, and capture unforgettable photos. Continue to the monastery of Agios Roukouniotis and the Old Windmill viewpoint, where the sun casts its golden glow over the Turkish Coastline.

After soaking in the breathtaking views, a short transfer brings you to Gyalos Town, where you rejoin your gulet. Dinner is on your own, allowing time to stroll the charming harbor streets or unwind on deck under the Aegean sky.

Cruising: 30 N.Miles (approx. 5 hours – stops included)

Hiking: 5.8 Km (Actual hiking time 3 hours)

Lunch on board / Dinner on your own

After a leisurely breakfast on board at Gyalos, your guide will walk with you through the beautiful alleys of Symi town including “Kali Strata” & the Upper Village neighborhood for great views. Then, you will step into the flavors of Symi with a hands-on cooking class. Using fresh, local ingredients sourced from the island, you’ll learn to prepare traditional Greek dishes — from vibrant salads and meze to classic mains — guided by experienced local chefs. It’s a chance to discover the secrets of Greek cuisine, taste your creations, and connect with the island’s culinary culture.

The afternoon is free to explore Symi at your own pace. Wander through the colorful streets, discover hidden corners and charming shops, or simply relax by the picturesque harbor, soaking in the island’s unique atmosphere. Dinner on board.

Walking: In Symi town & Chorio (approx. 1,5 hours)

Lunch in a taverna / Dinner on board