Customwalks: Guided walking tours in Italy, France, Greece, Spain, Turkey and Croatia.
Greece Dodecanese (South) Islands Hiking Tour Write a review
The Dodecanese are a group of 12 large Greek islands (plus 150 smaller ones) in the Aegean Sea. They are crisscrossed 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
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Greece Dodecanese (South) Islands Hiking Tour itinerary Request full itinerary
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 Island. Dinner included.
Enjoy breakfast on board and then disembark for a 2–3-hour 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. 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 Hike: 6.5 kms/4 miles, elevation gain 282 m/902 feet, duration about 2.5 hours in the morning on a good path, but very rocky underfoot when we explore the abandoned village. Overnight Chalki. All meals included.
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 hike 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 Hike: 7 kms/4.2 miles, elevation gain 279 m/893 feet, duration about 2.5 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. Possible other hike on Alimia island, out and back: 4.1 kms/2.4 miles, elevation gain 60m/200 feet, duration 1 hour. Overnight Symi. All meals included.
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, hike 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 hike: 5 kms/3 miles, elevation gain 291m/931 feet, duration about 2.5 hours. Initial climb 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.
A short morning cruise takes us to the start of today’s hike, 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 hike 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 Hike: Morning 4 kms/2.4 miles, elevation gain 100m/320 feet. Duration about 1 hour on a good dirt path and then gravel fire road. Optional 5.6 km/3.6 mile mid afternoon hike, elevation gain 206m/670 feet. Duration 2 hours. Late afternoon hike to cooking class: 3 kms/1.8 miles, flat, about 1 hour along a paved walkway. Overnight Symi. All meals included.
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. Hike 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. The Hike: 10.3 kms/6.1 miles, 618m/1,977ft elevation gain. Duration, 4hrs. Overnight Nisyros island. All meals included.
Disembark this morning for a hike 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 hike up to the ruins of another Crusader castle. The Hike: 4.5kms/2.9 miles, elevation gain 108m/330 feet, about 1.5 hours in the morning plus optional afternoon hike (or walking in Kos town). Dine on board tonight for one last farewell meal with your shipmates. Overnight Kós harbor. All meals included.
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: 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.
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 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 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.
5I 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!
5My 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 
5I 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!
5Gwen 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.
4.6A 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
5What 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
4.3A 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.
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.
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
by Megan C
