Kalymnos Round Island Trek

Kalymnos Trek – Round Island Challenge – 8 days

from £750.00

Discover the beauty and culture of the Aegean islands on this Kalymnos trek. Over eight days you will pass towering cliffs, whitewashed villages and turquoise bays. Your experienced guide will bring the island’s history to life, with visits to key archaeological sites and museums.

This trip also includes opportunities for sailing and snorkelling in the Mediterranean’s crystal clear waters. Book now for a complete adventure and cultural experience!

Click ‘reserve’ below to see available dates. If your preferred dates are not available, please contact us to enquire about alternative dates.

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  • Vacation Style Holiday Type
      Historic Challenge, Island Challenge, Peak Challenge
    • Activity Level Demanding
    • Group Size Medium Group
    All about the Kalymnos Trek – Round Island Challenge – 8 days.

    Kalymnos Island round tour – A Greek Island paradise challenge

    Duration: 8 days – 5 days trekking,  beach, museum visits, snorkelling and sailing.

    Accommodation: 7 night’s accommodation in hotels or stylish apartments.


    Kalymnos is a real paradise! On our round island trek we work in partnership with local Kalymnian people to provide you with a real insider experience of this beautiful island and its elegant and sometimes turbulent history. If your looking for an island holidays, you can take advantage of blissfully warm climates on the Greek Islands.  We are able to tailor the trip to your group and have visited the island many times. Some trails are almost hidden and known only to the Kalymnian hunters and shepherds. Be ready for exceptional fish dishes and jaw dropping views in Masouri.


    • Greek Agean Island paradise
    • Towering cliffs adorned with stalagtites
    • Whitewashed villages, turquoise bays and stunning beaches
    • Chora castle
    • See early Christian basilica columns and Hellenic acropolis
    • Explore the curious ash hills of Vathy and Rina harbour

    Dates available in April, May, June and October in 2018  and 2019 – please enquire.

    The tour package inclusions and exclusions at a glance
    What is included in this tour?Items that are included in the cost of tour price.
    • Local transfers
    • Boat trips in itinerary
    • Accommodation and meals as stated
    • Movement of luggage to allow walking only with a day sack
    • Guiding by an international mountain leader and/or local guide
    • Pricing assumes all participants arrive and depart on the same flight at Kos airport for single pickup. Participants arriving on different flights will incur additional airport pick up and/or drop off charge and only can be performed if it is possible with the logistics plan.
    Whats not included in this tour.Items that are not included in the cost of tour price.
    • International flights
    • Tips
    • Insurance
    • Snacks and some beverages
    • Telephone calls
    • Any changes outside the itinerary due to any client leaving the trip
    • Additional airport transfers outside the single timed group transfer
    • Boat journey from Emborios – Telendos and Telendos – Kalymnos (20€)
    1. Day 1 Arrival at Kos airport

      Masouri coast where we stay, sea food fiesta of the highest quality

      Transfer from the airport in Kos to our hotel. Stay the night at a beachside hotel on Kos with spa and pools with time to relax and enjoy this Agean paradise.

    2. Day 2 Arrival in Mastichari and sail to Pothia, Kalymnos. The Italian way and ash hills of Vathy

      Kalymnos Rina Bay

      Travel to Mastichari from Kos for catching a morning ferry to Kalymnos. Visit the Archaeological museum in Pothia and then walk following the Italian path to the ash hills of Vathy and the beautiful harbour of Rina (10km). Before leaving Pothia we have the chance to discover some beautiful local architecture. A chance to take a snorkelling trip before dinner from our family run hotel.  +400m,10km (B,L,D)

    3. Day 3 Walk Rina – Panaghia Kyra Psili church via the beautiful limionary bay 

      Local flora

      Walk Rina – Panaghia Kyra Psili church via the beautiful limionary bay. We then climb up past Aghia Makrina church +250m contouring around and up to Panaghia Kyra Psili church before dropping down to Pezonda bay. From here we are picked up by boat and transported back to Rina. Hotel. +450m, 9.5km (B,L,D)

    4. Day 4 Rina - Palionisos Bay (boat) - Sykati cave – Emborios

      Aghios Konstantines overlooking Kalymnos mainland

      After our boat journey around the island past many spectacular cliffs and coves we land at Palionisos bay and climb up to then drop down into sykati bay and see Aghios Georgios church and climbers before skirting the coastline to the stunning Vyzotos beach where there will be a chance to swim. We then climb steeply to the famous Sikati cave and onward to the ridge. Continuing along the crest of the island before dropping into Emborios. Emborios was a favoured harbour of the Phoenicians. Stylish apartments 9.4km, +450m (B,L,D) 

    5. Day 5 Sail from Emporios – Telendos Island and make a journey to the islands summit

      Beginning the climb to Telendos summit

      Telendos sits majestically off the coast of Kalymnos. We contour around just above the sea before heading up to Aghios Konstantinos church and then more steeply with some rocky steps to the summit of the island. After reaching the top 459m we head along the ridge before dropping down following cairns and then a better track towards the sea, avoiding impressive looking cliffs down and right. Telendos was once attached to the mainland before sinking into the sea after an earthquake in 554 AD.  We take a short ferry ride back to Myrties and walk into the lively village of Massouri – a climber’s paradise. An excellent range of restaurants and bars await with a breathtaking view of Telendos at sunset. Angelica, Vouros apartments or Plaza hotel. 13km +770m (B,D)

    6. Day 6 Climb from Myrties to Hora taking in the islands highest peak Prophitis Ilias

      Profit Ilias

      Climbing up from the town we pass the Symplgaedes climbing area on our right and enter a small valley. After some time it is neccessary to escape rightwards towards Prophitas Ilias and move up across the hillside underneath soome small cliffs before dropping down into a bowl. We contour around immerging through a metal gate. A second bowl leads to a small enclosure where we drop down and then head towards the valley floor. Once in the valley we head up and then break out on a clearly marked path to the Summit passing a church. Aghios Ioannis Theologhos. There is a stunning 360 degree panorama from the summit to take in before descending to Hora and Hora castle.

      This is one of the most beautiful and picturesque places on the Island. It is considered as the medieval capital of Kalymnos and the castle was inhabited until 1812. That night we stay close to Kantouni Beach. Hotel ( +676m,12.7km (B,D)

    7. Day 7 We visit Katouni beach and Platys Gialos

      Local customs

      A chance to go sponge shopping and relax before catching the boat back to Mastichari and Kos. You will probably already be planning your next visit! Many additional activities available. (B,D)

    8. Day 8 Departure Day

      Chora, Kalymnos

      Late morning flight departures from Kos airport. (B)

    Kalymnos Rina Bay
    Package Confirmed Dates Trip Status Trip Status Price (PP) Excluding Flights Price (PP) Including Flights  
    19/10/2019 - 26/10/2019