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Trekking the Kalymnos trail in Greece

Kalymnos trail
Kalymnos trail
Kalymnos trail
Kalymnos trail
Kalymnos trail

Discover the beautiful landscape and hidden secrets of Kalymnos island with this 8-day hiking tour in the company of IFMGA certified guide, Carlo.

Not specified

8 Days

Jun, Jul, Aug, Sep

Open to everyone



Spend 8 days hiking the beautiful Kalymnos trail in Greece and experience how it is to walk through an amazing and exotic area.

Kalymnos is a Greek island that forms part of the Dodecanese in the southeastern Aegean Sea. It was once famous for its sponge diving and trading activities but recently it is a popular rock climbing spot.

I’ve put together an 8-day hiking trip to take you to the many exotic and unknown trails that will give you an amazing perspective of this beautiful place.

So, we’ll go through many different paths. Some are old walking trails that connect ancient villages, others are shepherd tracks and there is also a path built by the Italian army during  the 1912 war with Turkey. And we’ll get to this paths by sailing on a boat through this beautiful blue sea.

So we’ll discover this remote spots and by doing so you’ll enjoy an amazing environment. You’ll also experience the boat rides which will give you a different perspective of the island. And, off course, you’ll enjoy the local food and the hospitality.

Sounds like an amazing adventure? It is! Send me request now and we’ll start planning your visit to the amazing Greek island of Kalymnos. You’ll spend an unforgettable week!

And if you’re looking for more 8 days sailing adventures please also check my Climbing and sailing on Kalymnos Island, Greece and my Elba & Capraia trekking and sailing in Tuscany.

Price includes

- Guiding fee

- Accommodation included

- Transport during the trip

- Breakfast

- Dinner


Day 1: Arrival

Flight to Kos and meeting at the Kos Airport. Transfer to the Marina and accommodation on the boat. The skipper will give a safety briefing. Sailing from Kos to Kalymnos, We will have to sail about 16 miles to the village of Pothia the main town on Kalymnos, a first contact with sailing that will be more or less exciting depending on the weather. Arrival in Pothia. Dinner in a taverna and sleeping on the boat.

Day 2: Warm up hike

We will warm up with a short hike, starting directly from the port in direction South. We will walk about 1 km on the road before turning to the path following the coast to the small church of Agios Georgios and from here to the bay and village of Vichadya where we will have dinner and find our boat for the night.

Day 3: Hike from Vichadya to the Bay of Linaria

A more strenuous day, double distance of the first day, about 8 km along the coast at an altitude between 150 and 200 meters. From Vichadya we will target the churches of Aghia Ekaterini, Aghios Andreas, the climbing wall of Pytari and one more church Aghios Costantinos. From here continue hiking until we reach the cliff of Saint Photis. We will find the boat and the skipper in the bay of Linaria. After a rest and a late lunch we will sail to the Island of Telendos where we are going to have dinner in a typical Greek tavern.

Day 4: Hike around Telendos island

We will walk around the island of Telendos and reach the top. After a big breakfast we start walking through the small village and follow the South coast of the island walking below impressive cliffs. This is a goal for climbers from all over the world. From here we will climb down, passing next to the church of Aghios Kostantinos, all the way to the sea level and close the loop reaching the village an about 4:30 hours. Snack, relax and a short sailing to the village of Emborios and the Island of Kalymnos. Dinner in one of the best restaurants of the island.

Day 5: Hike from Embrios to Sycati Bay

We will walk from Embrios to Sycati Bay. From the village we follow the trail taking us next to the climbing cliffs and later we continue following shepherd trails, sheep folds built in natural caves, stone stairs cut in the rock allowing us to pass where sheer walls would have stopped our way. We will climb to the highest point of the Patela peninsula (441 m) and from there down to the amazing Sikati Cave, a huge limestone hole formed when the ceiling of the cave collapsed. We can descend into the hole using some fixed ropes that are on the spot. From here to Sikati Bay where we will find the boat and the skipper waiting for us. It will be a 4:30/5 hours walk. With a short sailing we will go to the Palionisos Bay to a dinner on a balcony overlooking the sea. The rocking of the boat will not be needed to fall asleep.

Day 6: Hike to Vathi Village

The day starts with a short sailing to the Bay of Pezonda. From here we will walk to the village of Vathi, a tiny, beautiful natural harbour carved between steep walls and a green back country green of agriculture and citrus trees, an oasis in the barren island. We will walk partly by the sea and partly on higher ground but always surrounded by beautiful sights. Reaching the small village will be a great pleasure as well as trying the local specialties in the local tavernas. A deserved night sleep will follow.

Day 7: Hike on the Italian Path

A comfortable, short walk on the Italian Path, the beautiful paved mule-track built by the Italian soldiers in 1912 during the Italo-Turkish War. We will leave the port following the easy track and reach a saddle just below Agati Peak, and we will descend with a stunning view of Pothis, were we have started walking a week before. Once in the town we reach the port and board the boat. We will then cross to Kos where we will arrive in the evening, just in time for dinner. Small party to celebrate the end of the trekking. We will sleep in Kos Marina on the boat.

Day 8: Departure

Breakfast and transfer to the Airport. There are many interesting classic Greek ruins in Kos if your flight is in the afternoon.



Meeting point

Kos Airport.

About the guide

UIAGM/IFMGA Mountain Guide from Italy

I've been alpine guide since 1992, this profession has allowed me to realize my dream: to see the world, I accompanied for work, groups on the 5 continents.

The last challenge was to join the world of the mountain with the world of the sea, with my friend skipper Paolo, we founded mountain sailing and we propose climbing and sailing and trekking and sailing. Two totally different worlds with many aspects in common, a new extraordinary adventure.


Italian | French | English

What people are saying about Explore-Share

Kumari Selvakumar


Sept 14, 2022

I’m extremely happy with the ease with which I could book via your site reliable and experienced guide. Thank you so very much, and I’ve started to recommend your site to my friends. Dimitris is not only an awesome guide, but a wonderful person who was always looking out to give me the best experience I can have when he found out how much I love climbing! He is the Best!

Niklas Warren


Sept 6, 2022

I am very pleased with Explore-Share! This was my first international climb, and the communication and response time were great. Herbie is a very skilled guide and very efficient. The entire booking process & payment was smooth. I will definitely use Explore-Share again. Thank you.



Aug 23, 2022

I was looking for a local guide for a hike I was planning and came across Explore-Share. They seemed to have good reviews and so decided to give them a try. The experience was very positive and completely happy with their service. I will be using them again for next trip.

Colin Finnegan


Aug 17, 2022

Easy to set up and find the perfect trip. Informative site that is easy to use. Guides are all great to work with and communicate all arrangements needed. As simple as can be!

Lesley Weber


July 16th, 2022

Thank you explore-share for a wonderful via feratta experience. We have been wanting to learn for a long time but don't have the facilities in Scotland. The guide Mitja was extremely helpful and knowledgeable, answering all my many questions and providing advice. On the day head to take another group but he quickly arranged another guide Borut, who was brilliant. We had a fantastic morning learning via ferrata at Hvadnik in the gorge. It gave us the confidence to later hire our own equipment and go out in Mojstrana. Altogether a five star + experience. Thank you.

Richard Scrivener


July 20, 2022

Hello! I have been thoroughly impressed by the service and assistance that explore-share have provided the past couple years in helping to plan my trip to the High Tatras in Poland. I really appreciated the flexibility that they provided in allowing me to rearrange my trip twice owing to covid. They were responsive and communicative throughout. This trip was part of my Stag weekend celebrations and explore-share connected me with an outstanding guide in the form of Marcel - he was an excellent recommendation and we really enjoyed our guided hike in the High Tatras with him. Marcel was an outstanding professional, placed a high focus on preparing well and staying safe, and was also a great guy! Highly recommend. Many thanks and best wishes - Richard

Yvonne Morrison


May 8, 2022

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!

Mark Stone


April 14, 2022

Great service by explore share. Our guide, Fred, gave us a fantastic day. Totally wild adventure that would be impossible on our own. I’m really impressed. Thank you very much.

James Dempster


March 9, 2022

I can’t recommend this enough. Great service, great price and the on the ground team was top notch. Top marks all round.

Leonardo Rodriguez


March 4, 2022

Everything went very well! Above our expectations! Thanks Explore-Share and Thanks Kiliholidays! Great support from all you! Thanks for the hard work and excellent level of commitment.

Daniel Martinez


Feb 2, 2022

Excellent job making your platform available to all mountain lovers. Our guide Gabrielle was an excellent companion





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