Sailing and rock climbing week around the island of Kalymnos in Greece

Spend 8 days climbing and sailing around Kalymnos, in Greece, and discover a paradise for these activities along with experienced mountain guide Matteo.




Trip Duration

8 days

People per Guide

4 people

Trip Level


Offer Period

Oct, Nov

Type of Trip



  • Discover a paradise for sailing and climbing in Greece.

  • Spend the nights in a boat on the sea.

  • Contemplate stunning sea landscapes.


Have a fantastic time climbing and sailing all around the island of Kalymnos, a wonderful paradise for these activities. Follow me on this 8-day adventure in Greece.

During this program, we will explore the gorgeous islands, beaches and bays surrounding Kalymnos and spend the nights in a sailing boat. Also, we will enjoy climbing in beautiful spots and get to see incredible views right next to the sea.

Our boat will be available during the first two weeks of October, so you can choose the most suitable date for you in this period. It is a sailboat from 12 meters to 6 seats and it is divided into 3 cabins with two bathrooms.

For a more detailed description of the itinerary, take a look below.

Kalymnos is a paradise for the quality of the rock, the beauty of the sea landscapes and its food. Would you miss it? Send the request to book your place on this program now.

I also lead a rock climbing trip in Kalymnos. Check it out!

Show more

Price per person

Group of 1
5400 EUR

Group of 2
2800 EUR

Group of 3
2500 EUR

Group of 4
2000 EUR

Group of 5
1800 EUR

Group of 6
1700 EUR


Price includes

  • Guiding fee
  • Accommodation
  • Flight to the start of the trip
  • Meals: Breakfast, Dinner
 The price includes the flight from Milano to Kos, sailing boat for the week, mountain guide for the period, food for dinner and breakfast during all the period and climbing equipment. A minimum of 2 participants is required.


  • Day 1Milan - Kos - Mastichary - Myrties

    Flight Milan – Kos – taxi transfer to the port of Mastichary where we welcome the boat – transfer to Myrties – dinner on board.

  • Day 2Telendos

    Transfer to the island of Telendos and climbing on its walls. Dinner on board and night in the coast of Telendos.

  • Day 3Emporios

    Sailing to Ambelly Beach and climbing in the new Vasillissa sector. Dinner on the beach and night on radar at Emporios.

  • Day 4Sikati

    Sailing up to the beautiful bay of The Beach sector – climbing the sea and from here boat transfer in the beautiful Sikati Cave. Dinner on the beach with bonfire, night on radar at Sikati bay.

  • Day 5Palionnisos Bay

    Sailing to Palionnisos Bay and climbing – dinner on board and night on radar.

  • Day 6Vathys

    Sailing in the Vathys fjord – deep water only – dinner on board and night in the small port of Vathys.

  • Day 7Sailing on the island of Pserimos
  • Day 8Return to Kos - Mastichary - taxi transfer to the airport and flight to return to Italy

Other details

Skill level required


Fitness level required

Open to everyone

Meeting point

Milan, Italy.


Sailing boat.

More info

BOOKING: until the end of August


About the Guide


I live in the mountain for 300 days every year, I'm expecialized in trip around the world from Jordan (Wady rum for climbing) to Himalaya summit, during the summer I usually to work in the Alps (Mont Blanc and Monte Rosa) but during the autumn is a must to fly in Kalymnos to climbing.

I'm a guide from 2006 and from 2008 I work in Italy in mountain rescue Helicopter and I specialized in avalanche explosive working-from 2015, I become a teacher of italian mountain guide.



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What People are Saying about Matteo Canova


3 days for beginners, 2 days for more experimented .. and depending on the logging, difficulty increases ... should be more visible .. Booking was made personally but not by the organization team Pros: - Andreas’s skill as a guide, impressive - knowledge of the mountain - calm and patience Cons : - preparation required from Tete Rousse vs Goûter .. better information needed - extra costs related to the summit .. food, lift, trains , ....
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We were very satisfied with the whole experience. Our guide Matteo was very experienced and taught us a lot during the short trip. He looked after us and made sure that we felt secure even on the most dangerous stages of the ascent and descent. I cannot express enough how happy we were with Matteo\'s support and guidance. He was very professional during the whole trip and also very jovial and kept us a good company. His knowledge of the mountains and mountaineering is exceptional and I wouldn\'t hesitate to recommend him to anyone wishing to climb in the Alps.
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Maz Macys
We were a bit unlucky with the weather, so we didn\'t summit. But given the conditions, I think we did the best we could, we\'ve scaled some smaller peaks and practiced our spline skills. Matteo is great guide, highly recommend.
Read review
Vladimir Kamotski

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