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Dodecanese Islands, Greece

Dodecanese Island Hopping: Hike and Kayak in Greece

Enjoy an amazing guided hiking and sea kayaking tour around the Dodecanese Islands in Greece. Discover unique monuments and castles, as well as pristine beaches on an unforgettable adventure.


Private and Group


7 Days


Apr, May, Sep, Oct






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  • Hike, kayak and explore the beautiful Dodecanese islands in Greece.
  • Discover medieval villages, ruins, castles and monuments
  • Admire the awe-inspiring scenery and lovely beaches on the Aegean Sea


This guided hiking and sea kayaking tour around the Dodecanese Islands in Greece will enchant you with its crystal clear waters, ancient and medieval castles, villages, and ruins. Furthermore, you will love the colorful local culture and lifestyle of Rhodes, Nivadia, Tilos, and Halki.

The Dodecanese Islands are located in the Southeastern Aegean Sea. Our epic adventure begins on the main island of Rhodes, from where we will take a boat to Tilos while enjoying a delicious welcome dinner. From there, every day will be an adventure-packed fest of Greek island culture and fun.

Some of the exciting excursions we will enjoy include four hikes,  visiting the deserted Mikro Chorio village, a beautiful historical monastery, a medieval castle with a fortress, a deserted island, and, of course, many gorgeous beaches. We will hike between 2 and 4 hours each day, and also enjoy kayaking and boat transfers. On the last day of our adventure, we will return to Rhodes. You can find a detailed itinerary below.

This 7-day adventure provides breath-taking views and scenery at every turn – book now so you don’t miss out!

Price includes

- Accommodation included

- Guiding fee

- Breakfast

- Dinner

- Transport during the trip

- Permit and entrance fees

Secure your spot with just 25% payment

48-hour free cancellation with 30-day advance booking


Day 1: Arrival in Rhodes

Arrival in Rhodes and transfer to the port where we will embark on the boat to Tilos! We will start our adventure, enjoying a delicious welcome dinner.

Overnight in Tilos

Day 2: Hike Livadia - Lethra Beach - Mikro Chorio - Livadia

We start from the beautiful seaside village of Livadia and the trail leads us along the coastline to lovely beaches, including a red beach – due to the color of its sand. Once we reach Lethra Beach, a green tree-lined paradise, we begin the ascent towards Mikro Chorio(meaning small village in Greek). Once a highly 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.  After, we will return to our starting point in Livadia.

Distance: 7 Km

Actual Hiking Duration: 3 hours.

Overnight stay in Tilos

Day 3: Hike Livadia - Gera - Livadia

Today we start from Livadia village, and follow the coast line, walking by the beach, towards the end of the gulf, to the main port of Tilos.

The trail was once built at the ridge of the mountain slope and connected the port with the now abandoned village of Gera, where a few houses and some threshing floors remain, overlooking the endless Aegean Sea. We continue our walk, and go up a riverbed full of trees to reach the highest point of our hike. With great views of the nearby islands, we then descend again towards Livadia.

Day 4: Hike AG. Panteleimonas - Agios Antonios - Megalo Chorio

Agios Panteleimonas is a monastery built on 1531 AC by a sailor, who survived a shipwreck and had a vision of Saint Panteleimon in his dreams. He decided to build the monastery in the favour of the saint that saved him and as the myth goes, at the milestone of the building, he discovered a fountain! Nowadays, Agios Panteleimonas stands proudly on the harsh environment of a mountain slope surrounded by maple trees – a rare thing for an island. The trail starts at the outskirts of the Monastery and leads to Agios Antonios – the second port of the island, offering fantastic views of nearby Nisiros.

We arrive at Agios Antonios, and we ascend to Megalo Chorio (means in Greek: Big Village) the nowadays capital of Tilos. Built under the shadow of a medieval castle, Megalo Chorio stands proudly overlooking Eristos, the biggest and most famous beach on the island.

Day 5: Hike Nimporios - Chorio - Pondamos Beach - Nimporios

We start from the capital of Halki, Nimporios which is also the main village and port of the island. We walk uphill gradually from a fertile valley that leads up to the Medieval Castle of Chorio. The village of Chorio, west of Halki, once the only settlement on the island, is built around the hill upon where the fort stands with its old style stone houses. The village of Chorio was abandoned gradually and today is deserted. The views from the Castle are magnificent, and on a clear day, Rhodes, Nisiros, Karpathos and Tilos are visible into the endless blue of the Aegean sea. On the way back, we stop to Pondamos Beach for a refreshing swim and a homemade nutritious lunch at a seaside tavern.

Day 6: Half Day Hike to Alimia

Today we explore a deserted island, called Alimia. We set off from the port of Halki, and sail till we reach its first wide bay, where the main town once stood. This village was declared a protected settlement in 1978. We disembark there in order to hike through its untouched treasures. We will wander in forgotten trails, since the island is uninhabited since the 2nd 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 the Dodecanesse that time. We arrive to the second significant bay of the island, where we have the chance to swim to its crystal clear waters, and then enjoy a BBQ on the beach. At the early afternoon, we sail back to Halki.

Day 7: Departure

Trip Finishes.

About the guide: Trekking

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Tour Operator

Trekking Hellas is the largest and most renowned tour operator in Greece, in the outdoor holidays area. For over 33 years, we have been providing high quality services for individuals and groups, offering unique adventures in the most beautiful locations in the country, with highly qualified guides.

The variety of activities in offer is huge, from sea kayaking, hiking and rafting, to biking, via ferrata, rock climbing or gastronomy tours, among many others.

We operate 12 bases all over Greece, with different activities. The personnel in each base has the required qualifications to guide the specific activities we operate: eg. for hiking at low altitudes we work with experienced mountain guides with degrees from mountaineering associations and from our own training school; for sea kayaking we require the BCU certificate.

We contribute to the sustainable rural development by supporting local communities and offering work opportunities to their inhabitants, and the global effort to reduce over-tourism. We strongly embrace and implement a socially and environmentally responsible policy promoting the protection of nature and environmental awareness.

Our network makes it possible to offer and operate at the highest standards a variety of activities all over the country, in classic touristy destinations (Santorini, Athens, Crete, Rhodes, etc.) and less known regions of Greece (Tzoumerka, Karpenisi etc.).

Send us a request and come join us for a unique adventure in Greece!


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What people are saying about Trekking



Our first time with Explore-Share. An absolutely fantastic experience from start to finish. Extremely good value, very well organised with attention to detail. We travel widely and this has by far been the best of experiences. Well done to all concerned. We are already looking at booking another tri



George offered great introduction and guidance. Very patience and increased the level of climbing according to the participants. Great experience!



Our first time with Explore-Share. An absolutely fantastic experience from start to finish. Extremely good value, very well organised with attention to detail. We travel widely and this has by far been the best of experiences. Well done to all concerned. We are already looking at booking another trip!



George was a great guide, fun to talk to, informative, and attentive to safe. We all made great friends with him, and had a great experience.

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