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Greece Dodecanese (North) Islands Hiking Tour

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  • Location: Greece
  • Duration: 8 Day/7 Night
  • Departing from: Kos, at noon, Day 1
  • Tour finishes: Kos, 8 a.m., Day 8
  • Departures 2024: May 18, June 1, Sept 28, Oct 12, as well as private departures
  • Price 2024: Euro €4,600 per person for 8 to 10 participants (min 8 pax required) Euro €4,300 per person for 11 to 14 participants. Single supplement Euro €800. Two guides accompany departures of 9 or more people. Note: our Guaranteed Departure and Small Group Fee policies do not apply to this tour.

Join us in the Northern Dodecanese islands as we explore Kalymnos, Patmos, Leros, Pserimos, and Lipsi by boat and by foot. Each island is very different from the others. Kalymnos has mountains that plunge dramatically into the sea, while tiny Lipsi has gently undulating terrain. Verdant Patmos features the great Monastery of Saint John, one of Greece’s medieval treasures and a UNESCO World Heritage site, while Leros shows the architectural legacy of 30 years of Italian occupation before World War II.  We also anchor in the lee of little Pserimos; population 35. We use the boat to access hikes and remote areas of the islands so you experience them from a unique perspective not seen by most tourists. After a gorgeous hike amongst the hidden hills and valleys of the islands, relax on board your private yacht (a traditional Turkish-style “gulet”) and admire the view from the sea as you glide past sparkling bays and hilly headlands to moor in hidden coves. The warm waters (May departures the water is still “fresh”) of the Aegean provide ample swimming opportunities. You will also enjoy local cuisine in our favourite tavernas as well as freshly prepared meals on board. This is a fabulous week of exploration, relaxation, beautiful views, and wonderful cultural and culinary experiences.

Bodrum and Northern Dodecanese Islands Tour Includes

  • Accommodation: 7 nights on an all-wood, two masted gulet. All cabins have en suite flush toilets, stand-up shower stalls, and hot & cold water
  • Gulet Charter: a 65 to 90 ft. all-wood gulet with crew of captain, steward/s, and cook 
  • Charter expenses: all customs and harbour fees, electricity, fuel, and water
  • Meals: 7 breakfasts, dinners and lunches. Meals are either on board or in local tavernas, according to the itinerary.
  • Luggage: Bags are transferred to and from the gulet
  • Transport: All private van transfers as noted in the itinerary
  • Active days: 6 days of guided hiking
  • Guides: At least 1 bilingual Customwalks guide accompanies departures of 2 - 8 people; 2 guides accompany departures of 9 or more
  • Max group size: Tours are capped at 12 people


Booking: Please e-mail us at info@customwalks.com to receive a booking contract or simply click on the BOOK NOW button or the 'Contact Us' tab. Thanks!

Greece Dodecanese (North) Islands Hiking Tour itinerary Request full itinerary

Day 1

Arrive independently on the island of Kos, which has frequent air connections to Athens and some European hubs such as London. If you want to arrive a couple of days early, let us know and we can give you some hotel recommendations. Kos is the second largest island of the Dodecanese after Rhodes and has a rich history that is reflected in its architecture and historic monuments. It was the birthplace of Hippocrates, the “Father of Western Medicine,” and was an important city in both Greek and Ancient Roman times. The harbor is guarded by an imposing castle of the Knights of St. John, while 17th century Ottoman mosques stand next to austere Italian public buildings built during the Fascist period. There’s plenty to explore for a day or two! We meet today at 1 pm for lunch and then board the yacht at 4 pm at the lastest. A 1-hour cruise takes us to the tiny island of Pserimos, where we drop anchor in an idyllic little bay for a swim before dinner. Overnight Pserimos Island. Dinner included.

Day 2

Start your day with a refreshing swim before breakfast, which is served on deck and features fresh fruit as well as creamy Greek yogurt and other local specialties. We’ll eat while we motor over to the island of Kalymnos for the start of our first hike. We begin in the bustling port and continue up past the village on a military track built by the Italians in the 1920s. Climb up and over a ridge with stunning views over the sea and an inland valley before dropping down to the quaint village of Rina, which is tucked in at the end of a narrow inlet. Have a swim and then lunch, followed by an afternoon hikewhich passes ancient ruins on the way up to a cliff for dramatic views over the island. From there we have a short van shuttle to Emborious Bay, where we are reunited with our boat. Dine tonight in the garden of a colorful family-run taverna. Hiking: 2.5 hours in the morning, 2 hours in the afternoon. Overnight Kalymnos Island. All meals included.

Day 3

Leros Island
This morning echoes yesterday’s, with a morning swim followed by breakfast while cruising to another island: Leros. The hike takes us along the deserted coastline and then gradually inland past farms and white-washed chapels before descending into a forested gully with a WWII Italian bunker system. It is now an interesting museum about the 1943 battle for the island fought by German paratroopers and Allied troops. A further 40-minute hike brings us to Lakki harbor, a fascinating architectural “time capsule.” It was originally an Italian military base built during the Fascist period, so is an unexpected and striking tribute to Art Deco and Modernist Italian architecture. Our boat meets us here, and we have lunch on board, then enjoy a swim in a quiet bay before embarking on a late afternoon hike up to the medieval castle that dominates the island. Drop down into the village to enjoy a cold drink before dinner, which we have on shore this evening at one of the best restaurants in the whole of the Aegean. Hiking time: 3 hours in the morning, 1.5 hours in the afternoon. Overnight Leros Island. All meals included.

Day 4

Lipsi Island
Another relaxed morning awaits you, with a lovely morning swim followed by a hearty breakfast as we motor to the next island. Disembark on tiny Lipsi Island, where, according to myth, Odysseus was held for 7 years under a spell of the sea nymph Calypso. Disembark at the main village (the only human habitation on the island!) and begin a hike to the Five Martyrs’ Monastery and over to the other side of the island, which is completely wild and uninhabited. Descend to the beach to rejoin your floating home, which will take us to a quiet bay in the lee of a deserted island. Dinner on board. Hiking time 3 hours. Overnight Lipsi Island. All meals included.

Day 5

Patmos Island
We leave early this morning to cruise to Patmos Island and are dropped off at Psili Amos beach. From there we hike to Grikos Bay for a coffee break before climbing up to Chora, the island’s ancient capital and home to the Monastery of Saint John. A UNESCO World Heritage site, the village is a labyrinth of narrow whitewashed alleys, small row-houses, and chapels huddled beneath the massive walls of the monastery. Stop for lunch in the village and then head down to the west side of the island to a deserted beach where we meet our boat. Cruise Grikos Bay and then enjoy dinner on board. Hiking time 2.5 hours in the morning, and 2 hours in the afternoon. Overnight Patmos Island. All meals included.

Day 6

Leros Island
We have an optional morning hike back up to Chora, but this time from the east side, with a loop back down to Skala. You’ll have free time in the village and then an afternoon cruise to Leros Island, where we take a late afternoon hike along the wild northern coast to end at the lovely chapel of Isidorus, which sits at the end of a narrow isthmus in a secluded bay. Our mooring on the western side of the island affords us a gorgeous sunset before dinner on board. Hiking time is 2 hours in the morning, and 2 hours in the afternoon. Overnight Leros Island. All meals included.

Day 7

We have a morning cruise to the east side of mountainous Kalymnos Island, where we have a hike up to an enormous cave, whose stalagmites and stalactites can be seen through a narrow opening. The tiny trail traverses the hillside and eventually leads down to beautiful Palionisos Bay, where we can enjoy a cold beer, or a swim, or both. Have lunch here before boarding the gulet and cruising to Pserimos Island. There is an optional late afternoon hike before dinner on board. Hiking time 2.5 hours in the morning, plus optional one hour in the afternoon. Overnight Pserimos Island or Kos harbour. All meals included

Day 8

Morning departures from Kos
Disembark this morning at 08:00 a.m. You can stay on in Kos, or fly out from Kos airport today. Breakfast included.

Please note: Some details of the itinerary may change according to the departure date of your tour. Whenever we run a tour we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes they are bad, like a trail has been washed away. The result is that we sometimes change our itinerary to improve it by adding new wonderful elements to the tour or by removing something that does not work anymore. Rest assured, our goal is to always provide you with the best possible experience. We will advise you of any changes to the original itinerary prior to departure.  

Note on Itinerary: Although we do our best to adhere to the schedule listed above, this itinerary is subject to change for numerous reasons beyond our control, such as weather.

Activity Level 2 out of 5 = Easy to Moderate: 
In general: This is an Easy to Moderate tour for fit hikers, and with some effort do-able for not-so-fit hikers.
Terrain: Flat to gently rolling terrain with some rocky areas. Perhaps some short, relatively steep climbs and descents, but nothing longer than 20 minutes of sustained climbing or descents.
Actual hiking time: Between 2-4 hours per day, mostly in the morning but sometimes also in the afternoon.
Distances: Usually between 7 and 10 kms/4.5 and 6 miles. Max distance is 12 kms/7 miles.
Surfaces: Trails consisting of mostly compact earth, gravelly earth, and sometimes dirt-gravel roads.
Footing: Easy/good. Proper hiking shoes with thick soles with good treads are required. Sport sandals, running shoes and tennis shoes are not adequate.
Specifics: Flat to rolling terrain but often on uneven, rocky trails. Daily activity between 2-4 hours, mostly in the morning but sometimes also in the afternoon. Max distance 10 km (6 mi.). Note: a typical day starts with a drop-off from the boat and a morning hike of a few hours with a stop along the way. We often end the morning hike at a beach or cove where we are picked up by the boat. Then we have lunch, cruise to our next destination, and often have a short afternoon hike. This tour can become very easy if you choose to skip some of the hikes and enjoy relaxing on the boat! It's also slightly easier than our "classic" Dodecanese trip, which is rated 2+ for more challenging terrain.
Hiking Poles: Not required, but if you habitually use hiking poles then you will find them helpful.  
Compared to the Cinque Terre: This tour is significantly easier than the hikes in the Cinque Terre.
Other: This tour is appropriate for fit, first-time hikers who enjoy hiking. 
Easy to Moderate Tours: Puglia & Basilicata, Piedmont Hike. All of our boat–based tours in Turkey, Croatia, and Greece Dodecanese Islands would be “easy to moderate” IF you decide to skip the one or two of the more challenging hikes. Note: on our boat-based tours we usually do a hike in the morning, return to the boat for a swim and then lunch, then cruise, and then occasionally drop off for late afternoon hike. Your guides of course can advise you of the difficulty level and the terrain and footing of each hike.
As a point of reference, what is a 1 out 5 Activity rating? A 1 out of 5 rated tour is a tour without any hiking. Walks would be in towns, cities, and villages, and the countryside walks would be on paved, or gravel/dirt roads, and occasionally on some packed earth trails. Elevation gain and loss would be negligible.
As a point of reference, what is a 5 out 5 Activity rating? A 5 out of 5 rated tour is a tour that would be physically challenging and technically difficult even for very fit and experienced hikers. The hikes would have steep ascents and descents on narrow, exposed trails with challenging footing, such as on scree fields, or through rock falls and boulders. Distances would be up to 25 km/16 miles per day and feature ascents of over 1,000 m/3,200 feet in a day. A 5 out of 5 tour would also mean that you would be carrying a heavier-than-normal pack. None of our tours are rated 5 out 5. Our most challenging tours are 4.5 out of 5, and they are the Dolomites Alta Via (because of some exposed trail that requires some technical expertise) and our Republic of Georgia tour which has some long hikes with over 1,000 meters of elevation gain.

Getting There: The tour starts from Kos. Kos has frequent air connections to Athens and other European hubs. Flight time from Athens is 1 hour. We can also arrange airport pick-ups. You must be in Kos harbor no later than 3 p.m. There is a place to store your luggage if you arrive early in the morning, but most people prefer to arrive in Kos at least one day early, and spend the night.

Air: The closest airport to the start of the tour is Kos airport, which is well connected to Athens and some other European hubs. Aegean and Olympic airlines fly to Kos, as well low-cost flights from Paris, London and Amsterdam with companies like Ryan Air, Easy Jet and Transavia.

Getting Away at the End of the Trip: the trip ends in Kos at 8 a.m.

If you book a trip with us you will receive detailed information about how to get to and from the trip, and of course you can e-mail us with any questions.

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by S Lane
Posted Nov 08, 2018

This was our second time doing this trip and it was just as enjoyable as the first time. When bad weather forced us to spend the first night in Bodrum, the Customwalks team swung into action and we were taken on a guided walk above Bodrum and entertained in the evening by an expert on ancient artefacts recovered from the seabed, now housed in Bodrum museum. From then on the combination of early morning swims, interesting walks and delicious, healthy food on board made for a wonderful trip.We saw a pod of dolphins on our final day which was a perfect ending to a great trip.

If you have any questions or specific requests about any of our tours, we’re here to help. You can fill in the form below, send us an email, or call us and we’ll get back to you as soon as possible.

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This was our second time doing this trip and it was just as enjoyable as the first time. When bad weather forced us to spend the first night in Bodrum, the Customwalks team swung into action and we were taken on a guided walk above Bodrum and entertained in the evening by an expert on ancient artefacts recovered from the seabed, now housed in Bodrum museum. From then on the combination of early morning swims, interesting walks and delicious, healthy food on board made for a wonderful trip.We saw a pod of dolphins on our final day which was a perfect ending to a great trip.
by S Lane

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Patmos island, monastery of st. john
Food breakfast on deck
Leros island venetian castle
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Kalymnos town
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Dodecanese islands
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