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Greece Dodecanese (South) Islands Hiking Tour

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  • Location: Greece
  • Duration: 8 Days/7 Nights
  • Departing from: Kos, Greece or Bodrum Turkey, 13:00, Day 1
  • Tour finishes: Kos, Greece or Bodrum Turkey, morning of Day 8
  • Departures 2024: May 25, June 8, Sept 28, Oct 6 (Sunday), 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.

The Dodecanese are a group of 12 large Greek islands (plus 150 smaller ones) in the Aegean Sea. They are criss-crossed with ancient hiking trails and adorned with Byzantine churches, medieval castles, and charming whitewashed villages. The Dodecanese islands provide the ideal setting for our style of guided hiking tour: a mix of glorious land and seascapes, little-used hiking trails, friendly people, wonderful cuisine, and the luxury and romance of traveling by private yacht. And what a yacht! We have a gorgeous 28 to 30-meter (90 to 96 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.

Please note, most of our departures will start from Bodrum, Turkey. This is because we are usually unable to source a Greek-flagged gulet that is up to our high standards and therefore we use the excellent gulets and crews that have made Bodrum famous for their "Blue Cruises". When we use a Turkish-flagged boat we must embark and disembark in Turkey. If you book far enough in advance, we may be able to reserve the only good Greek-flagged-Turkish-built gulet that is sometimes available, in which case the tour can begin and end in Kos.

Greece Southern Dodecanese Island Cruise & Hike 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

Day 0

Yes, we have a day “Zero” on this tour because you will probably want to arrive either in Kos island (Greece) or Bodrum (Turkey) this evening or in Athens or Istanbul to be nearby for the start of the tour tomorrow. Let us know where you want to stay and we will suggest and book hotels for you. See our separate “Pre-departure” document for more information.

Day 1 Pick-up in Bodrum (Turkey)

Arrive independently in Bodrum, Turkey, today if you have not already stayed here the night before. Bodrum is a lovely town with a fascinating history and it is well worth a visit. We meet today at 13:00 for lunch in town (we have an office where you can store your luggage if required). We board the boat, usually at 15:00. After a pleasant 1.5-hour cruise, we arrive in Kos harbor, where our agents will clear us through Greek customs. While they do that, we can get off the boat and take in a sampling of the island’s rich history that is reflected in its architecture and historic monuments. The harbor is guarded by the 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. Weather and time permitting, we will leave for a 1 hour passage to tiny Pserimos island (population 130), where we moor in an idyllic bay. Dive into the crystal clear water or stretch your legs with a 45-minute loop hike before dinner dinner on board beneath the stars. Overnight Pserimos Island. Lunch and dinner included.

Day 2 Tilos Island

Enjoy breakfast on board as we cruise to Tilos Island. We disembark late morning for a hike along the coast and then inland to Mikro Chorio, an eerie village that was abandoned in the 1950’s. We hike amongst the ancient terraces of olive, walnut, and carob trees before descending to Lavidia village for a late lunch in a wonderful beachside taverna.  Later in the afternoon, those who want to get some exercise can disembark for a beautiful and relatively vigorous hike that follows an ancient trail that linked Tilos Port with a settlement of stone and thatch houses that have long been abandoned. Return to the boat for dinner on board. The Hike: Morning: 3 hours. 7.9 kms/5 miles. 310 m/990 feet Elevation gain and loss. Good path all the way. The final km is on a paved road to the village. Afternoon hike: 2 hours. 5.6 kms/3.5 miles. 195 m/620 feet Elevation gain and loss. It's a good, wide path most of the way, with the final km on a narrow, rocky path down to the beach. Overnight Tilos Island. Breakfast, lunch, and dinner are included.

Day 3 Chalki Island

Dive into the tranquil turquoise waters of the Aegean for an invigorating start to your day. Follow up with breakfast on board as we head for Chalki Island, one of the smallest inhabited islands in Greece. We pull into a spectacular mini fjord on the island's North side for a swim and lunch. Afterward, we drop off at the beach for a beautiful hike that takes us over the island's spine to Kania beach, where we enjoy a leisurely swim before getting back on board the yacht. A short cruise to Imborios lets you see the charming pastel-coloured village houses from the sea. We moor here and watch the last rays of the setting sun light up a line of stone windmills that sit in profile on a ridge above the village. Dinner is at our favorite seaside taverna in the village. The Hike: 2 hours. 5.4 kms/3.2 miles. 260 m/850 Elevation gain and loss. Rough, rocky path with a short, steep beginning. More gradual climb and then an easy descent on a rocky path. The final km is on a paved road to the beach.  Overnight Chalki Island. Breakfast, lunch, and dinner are included.

Day 4 Symi Island

A relaxed morning starts with a swim and then breakfast while looking onto the peaceful village of Imborious. We disembark for a hike up to the 13th-century castle of Saint John. The path takes us through the ruins and into the castle to a wonderful 360-degree lookout. We rejoin the boat for a short cruise to Alimia island, where we anchor for a swim and lunch in the horseshoe bay watched over by a crusader castle. An afternoon cruise brings us to the southern shore of Symi Island, where we get dropped on the beach to hike up a narrow path into the hills for a  spectacular south-to-north traverse across the island. The hike ends in colorful Symi town. At the turn of the 20th century, Symi was a prosperous port thanks to the sponge fishery. The town boasts stylish “mansions” built in the late 1800’s. Sadly, the island was bombarded during WWII and suffered an economic decline, which has recently been reversed as the Symi diaspora has returned to repair and restore their noble homes. The gulet will be tied up in the harbor, so you have time to explore Symi’s shops, cafes, and tavernas. This evening, we have a fabulous seafood dinner at a local taverna. The Hike: Morning: 2 hours. 5.6 kms with 270 m/860 feet of elevation gain and descent. Paved road, then stone flagstone steps that descend to a gravel road. Afternoon: 2 hours and 15 minutes. 290 m/930 feet of elevation gain and descent. Initial ascent on a narrow, rocky trail. Some asphalt road, descent on an ancient flagstone path to the top of Symi town, and stairs down to the sea. Overnight Symi town. Breakfast, lunch, and dinner are included.

Day 5 Symi Island, Cooking with Smeralda

We have a relaxed morning, breakfast on board, and then time for a swim in a sheltered bay before disembarking for a pleasant 45-minute coastal hike to our friend Smeralda’s charming traditional home on the beach. Here, we have a fun and informative cooking lesson. You’ll never skimp on olive oil again after seeing how much they lavish on their stuffed grape leaves! We enjoy lunch in their good company and then hike back to Symi village where you will have some free time to peruse the shops before returning to the boat. This evening, we anchor in a secluded bay whose spectacular limestone cliffs plunge into the sea. Dinner on board.  The Hike: Morning: 45 minutes. 2.5 kms/1.5 mile. Elevation gain negligible/ 70 m/250 feet. Afternoon: 1 hour. 3.5 kms/2.2 miles. Elevation gain is negligible. Overnight Eastern Symi Island. Breakfast, lunch, and dinner are included.

Day 6 Nisyros Island volcano walk

Our eastern-facing bay means the sun greets us first thing this morning, perfect for a pre-breakfast swim. We weigh anchor and cruise to the volcanic island of Nisyros. Upon arrival, we have a bus transfer to the white-washed village of Nikia for lunch. We then have a spectacular hike that takes us down from Nikia to Mandraki village along an ancient path that has existed since the time of Homer. Indeed, along the way we stop at the ancient Doric fortress that overlooks the coast. You will also hike above the volcano whose 4-km wide caldera provides a surreal landscape of smoking fumaroles and yellow sulfur-tinged vents. The path eventually loses itself amongst the labyrinth of white-washed alleys and lanes in enchanting Mandraki. We dine tonight at a superb waterfront restaurant before returning to your floating home. The Hike: 3 hours, almost all downhill. 11kms/6.4 miles 210 m/700 feet elevation gain, 630 m/2,010 feet elevation loss. Ancient flagstone paths, gravel paths, cobblestones, and some paved roads. Overnight Mandraki harbor, Nisyros Island. Breakfast, lunch and dinner are included.

Day 7 Nisyros to Bodrum

Disembark this morning for a hike through the narrow and colorful streets of the town, past white-washed houses with brightly painted balconies and shutters. 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 clearing customs in Kos and cruising back to the bustling port of Bodrum. Head into town for some last shopping or a snack of honey-laced baklava. The Hike: 1 hour in the morning. Dine on board tonight for one last farewell meal with your shipmates. Overnight Bodrum harbor.

Day 8 Departure from Bodrum

Your adventure concludes this morning after breakfast. We will be tied to the dock in Bodrum harbor so you can depart directly from the boat this morning, even for very early flights. We must disembark no later than 09:30. You can either fly out from Bodrum or return to Kos on the 9:15 ferry, which arrives in Kos at 9:45, and then catch a flight to Athens from Kos. If you want to do that, it is best to book flights after 13:00. You can also elect to spend a night in Kos and fly out the following day.  Breakfast included.

Note on Itinerary: 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.  

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 hikes 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 hike.


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 want 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 + out of 5 = 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. There are some short, but relatively steep climbs and descents. There are no sustained ascents or descents that last for longer than 30 minutes. The hikes are shorter in distance than those found on a 3 out of 5 rated tours. 

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 and on occasion rocky and uneven trails. There is one very short section where we climb up a narrow, steep trail where you will use your hands to steady yourself. There are lots of handholds and footholds, to help you, as well as a helping hand from your guides or fellow guests. This is only about 30 yards long and lasts for maybe two minutes. 

Footing: Good, but 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 hike of a few hours with a stop along the way. We often end the morning hikeat 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 hike. This tour can become very easy if you choose to skip some of the hikes 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 first-time “hikers” who enjoy hiking and who have good balance and are coordinated. 

Other 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 hikes on offer. On these trips, we usually do a hike 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 hike. Other Easy to Moderate Plus tours are: Tuscany Val d’Orcia & Maremma Hike and Provence Hike.

As a point of reference, what is a 1 out of 5 Activity rating? A 1 out of 5 rated tour is a tour without any hiking. Hikes would be in towns, cities, and villages, and the countryside hikes 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 of 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 and away: Due to recent changes in the regulations involving Turkish boats in Greek waters, we will be boarding and disembarking the boat in Bodrum, Turkey. You can either fly directly to Bodrum or fly to the Greek island of Kos and then take the fast ferry to Bodrum the morning of Day 1. After the tour, you could then fly out of Bodrum or return to Kos. We believe it is best to simply fly into Bodrum as it’s well-connected to European hubs. We can arrange for transport to pick you up at the airport (at no extra charge) and book a hotel for you if you want to arrive early. Bodrum is a fun and interesting place to stay for a couple of days. We will send you a comprehensive Pre-departure document that explains all of this in detail.

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.

5/5
RatingRatingRatingRatingRating  
5 out of 5
Ratings based on 20 Verified Reviews



Average ratings
4.9
Guides
4.8
Quality of itinerary
4.4
Food quality & variety
4.4
Value for money
4.9
Right amount of activity
4.8
Overall satisfaction

Reviews
5
by Denise B
Posted Jun 09, 2023

I cannot say enough good things about our tour to the Southern Dodecanese islands. Every part of the vacation exceeded my expectations: from the friendliness and aptitude of the entire staff to the beauty and historical relevance of the hikes. A typical day would start with a delicious breakfast on the boat followed by an exhilarating hike. During the afternoons we would usually visit a quaint, colorful island town, go sightseeing, or go for a swim off the boat. Our days were filled with fun adventures, and we didn't have to lift a finger to plan anything. Our fabulous Greek guide, Nefeli, taught us so much about the food, history, and culture. Brett was an impeccable planner, and every detail of the trip was well thought out and organized. The islands we visited had all the beauty and character of the more popular Greek islands but without the crowds. I highly recommend this tour. It's hard to imagine vacationing any other way now. We will be signing up for more Custom Walk adventures!

5
by Megan C
Posted Jun 07, 2023

My husband and I have just returned from a week-long, boat-based hiking trip with Brett and Nefeli in the Dodecanese (South) of Greece. It was one of the most amazing trips we've ever taken! I say this because every detail was taken care of for us: planning of hikes, food, beverages, transfers, etc. And this all came in a breath-taking setting of off-the-tourist- track jewel-colored islands in the Aegean Ocean. Brett and Nefeli planned interesting hikes for us each day, visiting ancient castles, towns, monasteries, even a caldera! The two of them have encyclopedic knowledge of Greek history so we had plenty of background info of whatever we were touring at the moment. They even arranged a cooking class in a private home with a mother/daughter team where we learned to make Spanakopita and other delights! Oh, and we had plenty of time for sunset sailing, sunbathing/relaxing on deck and swimming in that incredibly blue water. We would highly recommend Custom Walks to anyone looking for an active and educational vacation filled with good food, good cheer and good friends! We are already planning our next trip with them grin

5
by Saul
Posted Jun 06, 2023

I vacation in many places, and have done it many ways, but this last adventure was far and away the best. Everything was so well planned and orchestrated, the vacation "stress levels" were totally absent. Brett and his team are the ultimate professionals in customer care and their grasp on the history of the region we hiked through was excellent. Count me in as a custom walk vacationer for life!

5
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.

4.6
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

4.8
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!

5
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!

4.6
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.

4.3
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.

4.5
by Bruce and Linda
Posted Feb 11, 2015

Our second walk and sail and we loved it!



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

I cannot say enough good things about our tour to the Southern Dodecanese islands. Every part of the vacation exceeded my expectations: from the friendliness and aptitude of the entire staff to the beauty and historical relevance of the hikes. A typical day would start with a delicious breakfast on the boat followed by an exhilarating hike. During the afternoons we would usually visit a quaint, colorful island town, go sightseeing, or go for a swim off the boat. Our days were filled with fun adventures, and we didn't have to lift a finger to plan anything. Our fabulous Greek guide, Nefeli, taught us so much about the food, history, and culture. Brett was an impeccable planner, and every detail of the trip was well thought out and organized. The islands we visited had all the beauty and character of the more popular Greek islands but without the crowds. I highly recommend this tour. It's hard to imagine vacationing any other way now. We will be signing up for more Custom Walk adventures!
by Denise B


My husband and I have just returned from a week-long, boat-based hiking trip with Brett and Nefeli in the Dodecanese (South) of Greece. It was one of the most amazing trips we've ever taken! I say this because every detail was taken care of for us: planning of hikes, food, beverages, transfers, etc. And this all came in a breath-taking setting of off-the-tourist- track jewel-colored islands in the Aegean Ocean. Brett and Nefeli planned interesting hikes for us each day, visiting ancient castles, towns, monasteries, even a caldera! The two of them have encyclopedic knowledge of Greek history so we had plenty of background info of whatever we were touring at the moment. They even arranged a cooking class in a private home with a mother/daughter team where we learned to make Spanakopita and other delights! Oh, and we had plenty of time for sunset sailing, sunbathing/relaxing on deck and swimming in that incredibly blue water. We would highly recommend Custom Walks to anyone looking for an active and educational vacation filled with good food, good cheer and good friends! We are already planning our next trip with them grin
by Megan C


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