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Greece Dodecanese (South) Islands Hiking Tour

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  • Location: Greece
  • Duration: 8 Days/7 Nights
  • Departing from: Kos island, Greece, 12 noon, Day 1
  • Tour finishes: Kos Island, Greece, morning of Day 8
  • Departures 2023: May 6, Sept 23 & 30, as well as private departures
  • Price 2023: Euro €4,150 per person for minimum 6 participants (max 10 per boat). Single supplement Euro €660. Two guides accompany departures of 9 or more people. Note: our Guaranteed Departure and Small Group Fee policies do not apply to this tour.

The Dodecanese are a group of 12 large Greek islands (plus 150 smaller ones) in the Aegean Sea. They are criss-crossed with ancient walking trails and adorned with Byzantine churches, medieval castles, and charming whitewashed villages. The Dodecanese islands provide the ideal setting for our style of guided walking tour: a mix of glorious land and seascapes, little-used walking trails, friendly people, wonderful cuisine, and the luxury and romance of traveling by private yacht. And what a yacht! We have a gorgeous 32-meter (103 feet), all-wood, two-masted gulet with a crew of four to look after your every need. You’ll have plenty of time to relax on board and enjoy the warm waters of the Aegean as we sail from Kos island  to explore the nearby Greek islands of Kos, Nisyros, Chalki, Tilos, and Symi.

Greece Southern Dodecanese Island Cruise & Walk Tour Includes

  • Accommodation: 7 nights on a luxury gulet. All cabins have en suite flush toilets, stand-up shower stalls, and hot and cold water
  • Gulet Charter: an 60 to 100 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
  • Special events: Cooking class with local family, entrance to volcanic caldera on Nisyros
  • 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 (South) Islands Hiking Tour itinerary Request full itinerary

Saturday, Day 1

Arrive independently on Kos island, a short 1 hour flight from Athens. Let us know if you wish to arrive a day or two early and we can give you some hotel recommendations. After Rhodes, Kos is the largest island of the Dodecanese.It has a rich history that is reflected in its architecture and historic monuments. It was an important city in both Greek and Roman times and was occupied by the Knights of St. John and the Ottomans. We meet today for lunch at 1 pm. We can board the gulet at 4 pm at the latest. We then have a pleasant 3 to 4 hour  sunset passage to the island of Tilos. We moor in a quiet cove and then disembark for dinner at a wonderful local taverna in Tilos town. Overnight Tilos. Overnight Tilos Island. Dinner included.

Sunday, Day 2

Enjoy breakfast on board and then disembark for a 2-3 hour walk along the coast and then inland to Mikro Chorio, an eerie village that was abandoned in the 1950’s. We walk amongst the ancient terraces of olive, walnut, and carob trees. Loop back down to Tilos town to rejoin your yacht, which will then take us to a tranquil bay where we can have lunch, relax, and have a swim. We then have a 2-hour cruise to the island of Chalki, one of the smallest inhabited islands in Greece. We dine tonight outside in the main square under the boughs of a majestic carob tree. The Walk: 2-3 hours in the morning on a good path, but rocky underfoot when we explore the abandoned village. Overnight Chalki. All meals included.

Monday, Day 3

Treat yourself to a sweet “frappé” (traditional Greek iced-coffee) at one of the cafés lining the port and enjoy some wifi before heading out on this morning’s hike. We walk through the small but colorful village of Chalki town and then climb up to the imposing ruins of a castle built by the Knights of Saint John, once an important bastion during the Crusades. From this vantage point you can see over to the massive bulk of the island of Rhodes, and you may also catch a glimpse of your yacht as it cruises around to a quiet cove to pick us up after our descent. Have a refreshing swim and then lunch on board before setting “sail” once again to the island of Symi. We moor in a quiet cove beneath sweeping limestone cliffs and under the watchful eye of a tiny white-washed chapel. The Walk: 2-3 hours. Gradually uphill on a paved road, then a steep climb up to the castle on steps. Descend to the beach on wide gravel path. Overnight Symi. All meals included.

Tuesday, Day 4

Wake up with a morning swim and a hearty breakfast before heading out for today’s spectacular traverse across the island to colorful Symi town. This is our most challenging, but perhaps most rewarding, walk as we crest a high ridge and then gradually descend into town, which was once a stylish and wealthy seaport famous for its sponge-divers. We have a fabulous seafood lunch at a local taverna before rejoining our yacht to relax, have a swim, or do some shopping at the many boutiques in town. The walk (3 hours): ascent on a narrow, rocky, but good trail then descent on ancient flagstone path then stairs down to the sea. Dinner on board, then you’re free to wander into town tonight to check out the scene since we’ll be moored in the port. Overnight Symi town. All meals included.

Wednesday, Day 5

A short morning cruise takes us to the start of today’s walk, through a fragrant pine forest to the Agios Georgios monastery. Visit the historical chapel dedicated to Saint Michael before getting picked up by our gulet at the monastery jetty. We circumnavigate the island and return to Symi town, stopping first in a dramatic bay for lunch and the requisite refreshing swim. You have more time to shop and have another “frappé” in town this afternoon. Around 5 p.m. we have a walk on a quiet road that follows the coast into the neighboring bay, where we enter the charming and traditional home of Smeragda and her mother for a cooking lesson. You’ll never skimp on olive oil again after you see how much they lavish on their stuffed grape leaves! The walk: one hour in the morning on a good dirt path and then gravel fire road, then another 1.5 hours in the afternoon along a paved walkway. Overnight Symi. All meals included.

Thursday, Day 6

Weigh anchor this morning and cruise to the volcanic island of Nisyros. Upon arrival, we have a van transfer to the floor of the 4-km wide caldera, which provides a surreal landscape of smoking fumaroles and yellow sulphur-tinged vents. The last eruption was in 1888 and you can still feel the volcano pulsing beneath your feet. Walk down into the caldera itself and have a look around before departing on foot up to the whitewashed village of Nikia, which is perched overlooking the crater rim. Enjoy a frothy iced-coffee in the picture-postcard square then shuttle to a local taverna with delicious home-made food and sweeping views over the crater below. After lunch, transfer back to the town of Mandraki where you can explore the town or re-join the boat. Dine tonight at a waterfront restaurant before returning to your floating home. Overnight Nisyros island. All meals included. 

Friday, Day 7

Disembark this morning for a walk through the narrow and colorful streets of town, past whitewashed houses with brightly painted balconies and shutters. We gradually climb up to the massive walls of a 7th century BC Doric fortress with dominating views over the town below. Return to the yacht for a short cruise over to the tiny and uninhabited island of Gyali, which has been mined for its pumice for centuries. We moor here for lunch and a swim before eventually cruising back to the bustling port of Kós. Head into town for some last shopping, or opt for an afternoon walk up to the ruins of another Crusader castle. The walk: 2 hours in the morning plus optional afternoon walk (or walking in Kos town). Dine on board tonight for one last farewell meal with your shipmates. Overnight Kós harbor. All meals included. 

Saturday, Day 8

We have to disembark by 8 a.m. this morning, so you can schedule onward travel any time after that. If you need to get out earlier, there is usually a 6:45 a.m. flight back to Athens and we can help you get an early taxi. Breakfast included.

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.

Turkey vs. Greece: For those of you who have done our Turkish gulet tour, this is similar but very different. On both tours we travel by gulet, which is a fabulous way of getting around. The food is fantastic, and the comfort of lazing on deck, cold drink in hand and watching the sunset, is hard to beat, as is diving into the warm waters of the Aegean before breakfast. On this tour we often moor in little Greek villages because they are so delightful. Also, we want you to get a taste of Greek culture, both literally and figuratively. We will have several lunches and dinners in tavernas and the food is really excellent.The crew are always professional and yet friendly and obliging. The walks are similar to those in Turkey in that we usually drop off from the boat, hike, and we are then picked up again at the end of our walk.

It is different from our Turkish tour because:
One of the great features of the Greek islands are its beautiful villages and ports, while in Turkey it’s not the towns themselves that are the draw. The Greek villages have a rich patrimony and their own colorful architectural style.

  1. We thus spend more time in villages, both to enjoy their charm but also because there are fewer secluded bays than in Turkey. We will have two nights out of seven in secluded anchorages, and five nights in charming harbors.
  2. Dinners: we eat off the boat more often for dinner. Firstly, because we use a Turkish gulet and crew so we went to make sure you get a taste of the local cuisine. Secondly, it’s always fun to get out at night and mingle with the locals we meet along the way.

We can assure you that they are both fabulous tours.

Activity Level 2 + = Easy to Moderate Plus:
In general:
This is an easy to moderate tour for fit hikers, and will be a little challenging but do-able for less fit hikers.
Terrain: Flat to gently rolling terrain but with some rocky, rugged terrain. May have some short, relatively steep climbs and descents, but nothing longer than 30 minutes. The walks are shorter in distance than those on a 3-rated tour.
Actual walking time: Between 2 - 4 hours per day, mostly in the morning but sometimes also in the afternoon
Distances: Usually 7 - 10 km (4.5 - 6 mi). Max distance is 12 km (7 mi)
Surfaces: Trails consist mainly of compact earth and/or gravel and sometimes gravel roads, with frequent rocky and uneven trails
Footing: Good, but on occasion you have to pay attention to where and how you place your feet. 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 per day, mostly in the morning. 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 sometimes 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!
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 and have good balance.
Easy to Moderate Plus Tours: in this category are all of our boat–based tours in Turkey, Croatia, and Greece if you decide to do all of the walks on offer. On these trips, we usually do a walk in the morning, return to the boat for a swim and then lunch, then cruise, then sometimes drop off for another late afternoon hike, which you could skip and just relax on the boat. Your guides of course can advise you of the difficulty level and the terrain and footing of each walk. Other Easy to Moderate Plus tours are: Tuscany Val d’Orcia & Maremma Walk and Provence Walk

Getting There: The tour starts from Kos, which has frequent air connections to Athens and other European hubs. Athens is 1 hour flying time. We can arrange airport pick-ups. You must be in Kos harbor no later than 1 pm on day 1. 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. You can fly back to Athens, or take a ferry to another island.

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.

5 out of 5
Ratings based on 17 Verified Reviews

Average ratings
Quality of itinerary
Food quality & variety
Value for money
Right amount of activity
Overall satisfaction

by Gib J
Posted Apr 01, 2019

Gwen and I thoroughly enjoyed our greek island cruise walk in spite of a less than stellar week of weather. Hurricane and wind. Claire and Nefeli, our guides were terrific, adjusting to the weather on the fly. The hiking was a spectacular way to enjoy the islands especially when combined with the mornings and evenings on the sailboat and interacting with island natives.

by MG
Posted Nov 08, 2018

A great trip with plenty of unforgettable moment and highlights. The trip was made by the like-mindedness of fellow travellers and the enthusiasm of our guides. The choice of restaurants and eateries showcased the best of local cuisine. Possibly the activity level on some days was closer to a 3/5 than a 2/5 but that is to quibble because the views at the top always were worth the extra effort. We have unhesitantly recommended the trip and Customwalks to our friends

by R. Boas
Posted Jul 07, 2016

This was an outstanding trip in all respects--- the boat, the itinerary, the guides, the food, and the walks/hikes. We cannot recommend it highly enough. This was our third trip with Claire as our guide, and it will not be our last!

by P Allumbaugh
Posted Jul 05, 2016

What an awesome week in the Dodecanese Islands! I looked forward to this trip because of our wonderful trip to Turkey on a similar boat almost 10 years ago. Our group was very fun and easy and up for adventures each day. Our leader Claire was joined by Nefeli from Athens and provided insight and historical relevance to each of our hikes and the islands we visited. Our gullet was so much bigger than one for our Turkey sail - it felt luxurious and spacious. Houssain was a wonderful cook and each meal was beautiful and delicious -no telling how many photos we have of our meals! The hikes were strenuous and the views almost magical. For me there is nothing like hiking up to the top and looking down into another bay with our boat waiting on us! Thank you Claire, Nefeli, and Custom Walks for our wonderful vacation...for me a Bucket List trip!

by J&Y
Posted Jul 05, 2016

It was one of the best tours in my life. Our group from Atlanta, Cape Cod and Tokyo was great with our best guides and a chef. We will do another trip to Sicily soon! P.S. If we could have laundry service on the boat, it would be the best.

by P&S
Posted Feb 16, 2015

A unique experience. Highlights of the tour for us were the beautiful islands; meeting our fellow tour mates and our boat. The accomodations were comfortable, the food was excellent and the crew was friendly and helpful. Brett and Yorgos did a great job as guides. Parts of some of the walks would challenge the weekend hiker but overall they were enjoyable. We had fun.

by Bruce and Linda
Posted Feb 11, 2015

Our second walk and sail and we loved it!

by S Lane
Posted Feb 09, 2015

We have loved all the Walk and Sail tours, we are doing another one this year. The combination of scenic walks, wonderful swimming locations, living on a boat and eating and drinking well, is hard to beat. There was a good variety of walks on this tour, some very pretty villages, the most beautiful bay I have ever swum in, excellent guides. If you haven't tried one of the walk and sail tours, what are you waiting for?

by K.Gould
Posted Feb 03, 2015

Such a great combination - walking and cruising, looking forward to great food and company aboard our gulet after glorious days exploring these picturesque Greek islands. No mean feat to co-ordinate walks and boats between islands but Brett and Yorgos did this with aplomb and plenty of humour.

by T Woodall
Posted Feb 03, 2015

Sail and walk tours are great fun with lots of different challenges each day. Claire and Brett provided their usual high degree of professionalism along with a heavy dose of laughter and fun. Greece is simply magnificent.

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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Italian operations office

Gwen and I thoroughly enjoyed our greek island cruise walk in spite of a less than stellar week of weather. Hurricane and wind. Claire and Nefeli, our guides were terrific, adjusting to the weather on the fly. The hiking was a spectacular way to enjoy the islands especially when combined with the mornings and evenings on the sailboat and interacting with island natives.
by Gib J

A great trip with plenty of unforgettable moment and highlights. The trip was made by the like-mindedness of fellow travellers and the enthusiasm of our guides. The choice of restaurants and eateries showcased the best of local cuisine. Possibly the activity level on some days was closer to a 3/5 than a 2/5 but that is to quibble because the views at the top always were worth the extra effort. We have unhesitantly recommended the trip and Customwalks to our friends
by MG

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