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Greek Northern Dodecanese Island Cruise & Walk

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  • Location: Greece
  • Duration: 8 Day/7 Night
  • Departing from: Kos Island, 1 p.m., Day 1
  • Tour finishes: Kos Island, 8 a.m., Day 8
  • Departures 2019: September 28, as well as private departures.
  • Price 2019: Euro €3,600 per person for minimum 6 participants (max 10 per boat). Single supplement Euro €500. Two guides accompany departures of 8 or more people. Note: Our Guaranteed Departure and Small Group Fee policies do not apply to this tour.

We love our hiking and yachting trip in the Greek Islands so much that we’ve developed another one! Join us in the Northern Dodecanese island chain as we explore Kalymnos, Patmos, Leros, Pserimos, and Lipsi islands. Each island is very different from the other. 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 WW2.  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 walk amongst the hidden hills and valleys of the islands you 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 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.

Greek Northern Dodecanese Island Cruise & Walk itinerary

Day 1 -- Saturday

Pick-up in Kos and departure for Pserimos
Arrive independently on the island of Kos, which has frequent air connections to Athens and some European hubs. 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 now 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 p.m. for lunch in town, and then board the boat for a 1-hour cruise to Pserimos, where we drop anchor in an idyllic little bay for a swim before dinner. Overnight Pserimos Island.

Day 2 - Sunday

Kalymnos Island
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 walk. 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 walk which 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. Walking: 2.5 hours in the morning, 2 hours in the afternoon. Overnight Kalymnos Island. 

Day 3 - Monday

Leros Island
This morning echoes yesterday’s, with a morning swim followed by breakfast while cruising to another island: Leros. The walk 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 walk 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 improbable and striking tribute to Art Deco and Modernist Italian architecture. Our boat meets us here, and we have lunch on board and then enjoy a swim in a quiet bay before embarking on a late afternoon walk up to the medieval castle that dominates the island. Drop down into the village to enjoy a cold drink or an ice cream before dinner, which we have on shore this evening at one of the best restaurants in the whole of the Aegean. Walking time: 3 hours in the morning, 1.5 hours in the afternoon. Overnight Leros Island.

Day 4 - Tuesday

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 walk 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. Walking time 3 hours. Overnight Lipsi Island.

Day 5 - Wednesday

Patmos Island
We leave early this morning to cruise to Patmos Island and are dropped off at Psili Amos beach. From there we walk 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. Walking time 2.5 hours in the morning, and 2 hours in the afternoon. Overnight Patmos Island.

Day 6 - Thursday

Leros Island
We have an optional morning walk 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 walk 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. Walking time is 2 hours in the morning, and 2 hours in the afternoon. Overnight Leros Island.

Day 7 - Friday

Kalymnos Island
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. Walking time 2.5 hours in the morning, plus optional one hour in the afternoon. Overnight Pserimos Island.

Day 8 - Saturday

Morning departures from Kos
We start motoring early from Pserimos to be at Kos harbor by 8:00 a.m., when we have to disembark the boat. We’ll find a place to store our bags, and then usually transfer to the airport at 9:45 for the 11:55 flight to Athens. There is also a flight at 6:45 a.m. back to Athens if you need to get out earlier.

Trip Design:

Brett spent two weeks on the islands in June 2015 researching the hikes, moorings, and restaurants and developing the logistics of the tour. We then ran the tour for seven participants later that year. It was a great success, and those of you who have already done our Southern Dodecanese tour will see that the islands of the North are substantially different, so you will not feel like you are repeating the same experience. However, the wonderful formula of life on the gulet interspersed with hiking, swimming, delicious food, and great camaraderie remains a winner.

Activity Level 2 = 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 walking 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 walk of a few hours with a stop along the way. We often end the morning walk 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 walk. This tour can become very easy if you choose to skip some of the walks 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 walking. 
Easy to Moderate Tours: Puglia & Basilicata, Piedmont Walk. 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 walk 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 walk. 

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.

Trip Cost Includes: 7 nights’ accommodation on the gulet; 7 breakfasts, lunches and dinners; all entrances as per itinerary; all van transfers and luggage transfers as per itinerary; at least one bilingual Greek–English Customwalks guide.

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Getting There: The trip begins on the Greek island of Kos. There are frequent flights from Athens as well as with various low-cost airlines from London and other European hubs. You must be in Kos harbor no later than 13:00.

Air: You can fly into Kos's "Hippocrates" airport from Athens on the Greek national airlines like Aegean and Olympic, but there are also low-cost flights from Paris, London and Amsterdam with companies like Ryan Air, Easy Jet and Transavia. Airline companies and flights change surpringly often, so see the airport website for the most current information.

Getting Away at the End of the Trip: the trip ends back in Kos at 8 a.m., so you can book a return flight for the last day of the trip.

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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4.8
by S Lane from Crawley, UK
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.



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 from Crawley, UK

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