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Greek Dodecanese Island Cruise & Walk

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  • Location: Greece
  • Duration: 8 Days/7 Nights
  • Departing from: Kos island, Greece, 1 p.m. Day 1
  • Tour finishes: Kos island, morning Day 8
  • Departures 2019: May 11 & Sept 28, as well as private departures.
  • Price 2019: Euro €3,600 per person for minimum 6 participants (max 10 per boat). Single supplement Euro €600. 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 every need. You’ll have plenty of time to relax on board, and enjoy the warm waters of the Aegean as we sail and explore the islands of Kós, Nisyros, Chalki, Tilos, and Symi.

Greek Dodecanese Island Cruise & Walk itinerary

Saturday Day 1: Independent arrival on Kos Island

If you want to arrive a couple of days early and unwind on Kos before joining the boat, let us know and we can supply you with hotel recommendations.  We can also organize a hotel and/or guided visit in Athens if you wish to tour the famous Acropolis. Given that Kós is the second largest island of the Dodecanese after Rhodes, it has a rich history that is reflected in its architecture and historic monuments. The harbor is guarded by an imposing castle of the Knights of St. John, while 17th century Ottoman mosques and buildings stand next to austere Italian public buildings built during the fascist period. Extensive Hellenistic and Roman remains lay amongst public gardens. After arrival in Kos, board the boat and set out for a 3.5 -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.

Sunday Day 2: Tilos Island

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.

Monday Day 3: Chalki Island

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.

Tuesday Day 4: Symi Island

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.

Wednesday Day 5: Symi Island, Agios Georgios monastery walk

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.

Thursday Day 6: Nysiros Island volcano walk

Weigh anchor this morning and cruise to the volcanic island of Nisyros. Upon arrival, we are shuttled to a very local taverna with a stunning view overlooking the (still active) volcanic crater. After lunch, we are transferred 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. Our local guide explains the fascinating natural phenomena before we depart on foot to climb out of the caldera, up to the whitewashed village of Nikia, which is perched overlooking the crater rim. Enjoy a cool drink in the picture-postcard square, then shuttle back to Mandraki port where we will rejoin the boat. We dine tonight in the village, beneath a centuries-old fig tree. The walk: 2-3 hours including visit of the caldera, all uphill once we leave the crater. Overnight Mandraki harbor.

Friday Day 7: Nisyros to Kós

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.

Saturday Day 8: departure back in Kos

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.

Activity Level 2 + = Easy to Moderate Plus:
In general: This is an Easy to Moderate tour for fit hikers, and a little challenging but do-able for not-so-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 of sustained ascents or descents. The walks are shorter in distance than those found 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 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 and on occasion 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 who have good balance and are coordinated. 
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

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, 7 lunches and 7 dinners of which one is a cooking experience with a local family; guided visit of Nisyros volcano with certified local guide, all entrances as per itinerary; all van transfers and luggage transfers as per itinerary; all costs related to the boat charter and operation, such as fuel, port fees, and custom fees, at least one bilingual Greek–English Customwalks guide.

Not included: air travel to Kos, airport/hotel transfers not mentioned above; travel insurance; beverages other than water at meals; extra boat provisions (beer, wine, soft drinks etc); and items of a personal nature.

Booking: e-mail us at info@customwalks.com to receive a booking contract (or use the 'Contact Us' link at the top of this page), or click on the 'Book Now' button to the right.

Insurance: We highly recommend the purchase of Trip Insurance. We recommend “Travel Guard” to our North American clients, just click on the logo below. Australian, New Zealander, and British travelers, please consult your insurance brokers.**

Turkey vs. Greece: For those of you who have done our Turkish gulet tour, I can tell you that 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:

  1. 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.
  2. 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.
  3. 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.

I can assure you that they are both fabulous tours.

travel Guard insurance

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 1 p.m.

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 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.

4.58 out of 5
Ratings based on 16 Verified Reviews

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

by MG from Richmond
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 from Atlanta, GA --USA
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 from Atlanta Georgia
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 from Tokyo Japan
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 from Bedford, Canada
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 from USA Arlington Heights
Posted Feb 11, 2015

Our second walk and sail and we loved it!

by S Lane from Crawley, UK
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 from Bodrum, Turkey
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 from Atlanta, Georgia USA
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.

by LNichols from Purcellville, VA, USA
Posted Feb 02, 2015

It is not often that one can travel on a serious sailing vessel and have so much fun. The hiking was sometimes challenging; the scenery was always wonderful. The diverse group was fun to be with - dancing on the boat after dinner - and lots of good company. On the homeward voyage to Kos Capt. Ishmael raised the sails on a beam reach and we quietly enjoyed the sun and the sea.

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 from Richmond

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