Kalymnos Round Island Trek
sicati cave
Galini Hotel Vathy

Greek Island Hiking – Kalymnos Round Island Challenge, trek and by boat – 7 days MAY I JUNE I OCT


Hiking Greek Islands: explore off-the-beaten track treasures

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.

Click ‘reserve’ below to see available dates. If your preferred dates are not available, please contact us to enquire about alternative dates. There are many flights with Jet2 from the UK to Kos from May – the end of October and also with Easyjet. We are happy meet you on Kalymnos if you wish to fly a day early or arrive before the trip and co-ordinate a meeting point. Generally flights back to the UK depart late on your final day.


November: 6-12 November 2023

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  • Vacation Style Holiday Type
      Historic Challenge, Island Challenge, Peak Challenge
    • Activity Level Challenging - Trip grade 2
    • Group Size Medium Group
    All about the Greek Island Hiking – Kalymnos Round Island Challenge, trek and by boat – 7 days MAY I JUNE I OCT.

    Kalymnos Island round tour – A Greek Island paradise challenge

    Duration: 7 days – 5 days trekking,  beach, museum visits, snorkelling and sailing.

    Accommodation: 6 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 May, June and October in 2020 and 2021 – 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.

    What is 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 and transfer to Mastichari


      From the airport, it is 10 minutes drive to the port of Mastichari to reach our ****hotel with pools and private beach. Mastichari Bay Hotel is set in waterfront gardens and has a small private beach with jetties and it’s own nearby farm providing organic produce for it’s restaurants. Enjoy time to relax and enjoy this Agean paradise. From the airport, it is 10 minutes drive to the port of Mastichari. 

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

      In the morning we will take one of the fast and slow ferries across to Kalymnos which go every 2 hours more or less from Mastichari. It takes 20 to 50 minutes to get to Pothia (Kalymnos main port) where we will begin our trek after a visit the Archaeological museum in Pothia. Before leaving Pothia we have the chance to discover some beautiful local architecture. In the afternoon we commence along the Italian path to the ash hills of Vathy and the beautiful harbour of Vathy Rina (10km).

      Vathy and is the name of the valley, rich in citrus fruits, while the village around the harbour is called Rina. This charming village of Kalymnos is known for its simplicity and authenticity. The small harbour is surrounded by colourful bougainvillea under which lie a couple of tavernas and cafes. The water of the sea, very clean emerald green color, along with spectacular walls of the fjord, making the landscape very suggestive. 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 

      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 to Hotel Galini.

      In a cave on the mountain, north of Vathys, the monastery of Panagia Kyra Psili is located. It was believed the monastery was built by a Kalymnian who had migrated and refused the christian religion, but believed in God again when he returned to the island and got reconnected with his roots. It is also believed that a shepherd, looking for a goat that had disappeared, discovered the cave by chance. Stepping into the cave, he found an icon of Virgin Mary and tried then to take it to his village.  +450m, 9.5km (B,L,D)

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

      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 necessary to escape rightwards towards Prophitas Ilias and move up across the hillside underneath some small cliffs before dropping down into a bowl. We contour around emerging 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 Katouni beach and Departures

      Local customs

      A chance to go sponge shopping and relax before catching the boat back to Mastichari and Kos. We depart for the airport in the evening.  (B,D)

    Kalymnos Rina Bay

    Mastichari Bay Hotel**** or similar

    Vathy – Rina Harbour, Hotel Galini

    Emborios Apartments

    Massouri/Myrties – Hotel or apartment accommodation in this stand out village with superb restaurants

    Panoramos Hotel


    There are many amazing restaurants on Kalymnos and we will have the option to eat exxcellent quality fish and other tasty Greek dishes every night.