Northern Dodecanese Greek Island Cruise & Walk
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 five new islands (Kalymnos, Patmos, Leros, Pserimos, and Lipsi), each very different from the other, with the beginning and end in lovely Kos. 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 legacy of 30 years of Italian occupation (the entire island chain was taken over by Italy in 1912 and wasn’t formally returned to Greece until 1947). And Pserimos, with only 35 permanent residents, is famous for producing sea captains! We have carefully designed walks that allow you to experience the islands from a unique perspective not seen by most tourists. After the walk, relax on board your private yacht (a traditional Turkish-style “gulet”) and admire the islands from the sea as you glide past sparkling bays and hilly headlands to moor in unpopulated coves. The waters of the Aegean will be nice and warm, and there are ample opportunities to swim. 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, and beautiful views combined with wonderful cultural and culinary experiences.
Northern Dodecanese Greek Island Cruise & Walk itinerary
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.
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.
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.
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.
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.
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.
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.
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.
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 rating: 2+ out of 5 = Easy to Moderate: Flat to rolling terrain but often on rugged, rocky trails. Daily activity between 2-4 hours per day, mostly in the morning but sometimes also in the afternoon. Max distance 12 km (8 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. Often we 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 then 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!
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.
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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