Arrive in Bodrum, Turkey and meet the group at the gullet in the city’s grand harbor. Welcome drinks await us aboard and we are ready to disembark! First stop is Kos’ bustling port. This is the second largest island of the Dodecanese after Rhodes with a rich history reflected in its architecture and historic monuments: the harbor is guarded by the imposing castle of the Knights of St. John, in the town 17th century Ottoman mosques stand next to austere Italian public buildings, built during the fascist period while extensive Hellenistic and Roman remains lay amongst public gardens. After a short walking tour in the city’s historical center, we will have lunch and set out for a 3.5 -hour sunset passage to the island of Tilos. Tonight, we moor in a quiet cove and dine at a wonderful local taverna in Tilos town.
Overnight in Tilos
Lunch and dinner included
Cruise time:
Bodrum to Kos 2 hr
Kos to Tilos 3 hr 30min
Enjoy a Mediterranean breakfast that includes fresh fruits, olives and some of the best yogurt in the world and disembark for a hike to one of the smallest and least inhabited islands in the country. We walk across the coast for stunning views of the Aegean Sea. On first sight, the island seems to be bare and barren but as we follow the old stone trail to the inland, it soon becomes apparent that the dramatic landscape is less hostile than expected. We hike amongst ancient terraces of olive, walnut, and carob trees. The footpath winds uphill to the abandoned medieval settlement of Mikro Chorio. Today out of the 220 houses of the village, only the ruins of impressive stone houses can be seen. Round threshing circles, olive pressing stones and cisterns stand witness to Tilos’ intense agricultural past activity. We loop back down to Tilos town to rejoin our yacht. It is time to swim and enjoy Greece’s azure waters! In the afternoon we travel to the island of Chalki.
Overnight in Chalki
Breakfast, lunch and dinner included
Hiking distance: 7 km / Hiking Duration: 3 hr
Sailing distance:
Tilos to Chalki 3 hr
Forget Tilo’s cubic whitewashed houses, the town of Chalki is brightly colored with 19th-c. Neoclassical houses and ceramic-tiled roofs. Some of these houses are right on water, and residents dive from their front patios right into the port’s crystal-clear waters. We walk through the 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 look over to the massive bulk of the island of Rhodes, and you may also catch a glimpse of our 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. Tonight we moor in a serene, isolated cove to sleep under the stars.
Overnight in Symi
Breakfast, lunch and dinner included
Hiking distance: 6 km / Hiking Duration: 3 hr
Sailing distance:
Chalki to Symi 2 hr / 30 min
Wake up with a morning swim and get ready for today’s spectacular hike which is the most challenging but perhaps the most rewarding one in our trip. Our dinghy will take us on the beach to start our hike which initially ascends steeply on a narrow cliff. Soon we reach at the top and the sea views are breathtaking. Symi is the first island we visit which has a forest. So, as we traverse across the island towards the colorful town of Symi the landscape alternates between stark limestone mountains, the deep blue sea and the green of the cypress tree forest. Our flagstone path gradually descends taking us to the town. The first sight of Gialos harbor is unforgettable.
Two-story, pastel-colored neoclassical houses, with tall windows and doors are built amphitheatrically on the slopes rising on all sides. And above all, today we are having a fabulous seafood lunch overlooking at the sea. In the afternoon you are free to wander around and do some shopping at the numerous boutiques in town since we’ll be moored in the port.
Overnight in Symi
Breakfast, lunch and dinner included
Hiking distance: 6 km / Hiking Duration: 3 hr
A short morning cruise takes us to the starting point of today’s hike. We walk through a fragrant pine forest to the Archangel Michael Monastery on the southern end of the island. Built in the early 18th century, the monastery overlooks the bay in a truly magical setting surrounded by green hills. Visit the historical chapel which stands as one of the most important pilgrimage destinations of the country before getting picked up by our gullet. It is time for a swim and we circumnavigate the island to reach the spectacular Ai-Giorgis beach. Surrounded by sheer cliffs that make access by land impossible, this natural bay has gorgeous waters, small pebbles and a little church that gave it its name. Around 5 p.m. we return back to Symi town for our cooking lesson. The traditional home of Smaragda is outs of town in a neighboring bay so we walk on a quiet road that follows the coast. We learn how to make tzatziki sauce, stuffed tomatoes and spinach pie all baked in a wood oven. Just step back in time and feel the warmth of Greek hospitality in all its generosity.
Overnight in Symi
Breakfast, lunch and dinner included
Hiking distance: 2 km / Hiking Duration: 1 hr
Weigh anchor this morning and cruise to the island of Nisyros which is Greece’s youngest volcano. This tiny, round island has only four villages: Mandraki and Pali are on the coast, while Emporeio and Nikia are perched on the edge of the volcano’s crater. Upon arrival, we are shuttled to Emporeio for lunch at Katina’ s restaurant, a family taverna with stunning view overlooking the volcanic crater and local delicacies such as pythia (chickpea fritters) served with an almond-and-garlic sauce. After lunch, we are transferred to the floor of the 4-km wide caldera to walk inside Stefanos crater. Such visits are a once-in-a-lifetime opportunity, given that craters are rarely accessible and feels like you are walking on the moon! We depart on foot to climb out of the caldera, up to the whitewashed village of Nikia. This short but beautiful hike will reward us with extraordinary views. Enjoy a cool drink in the picturesque square before we head back to Mandraki port where we will rejoin the boat. We dine tonight in the village but this time we experience a modern version of Mediterranean cuisine.
Overnight in Nisyros
Breakfast, lunch and dinner included
Hiking distance: 3 km / Hiking Duration: 2 hr
Disembark this morning for a walk through the narrow and colorful streets of Mandraki 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 to the 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 port of Kós to clear customs and then back to Boldrum Turkey. Tonight we will enjoy our farewell dinner on board for one last meal with our shipmates.
Overnight in Bodrum
Breakfast, lunch and dinner included
Sailing distance:
Kos to Bodrum 2 hr
Nisyros to Kos 2 hr
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 Istanbul, we can help you get an early taxi.
Breakfast included
We are constantly updating our unique itineraries based on new information and experiences available. The walks, accommodations, and visits listed may be adjusted. The itineraries presented are subject to modification and change by Tripin Adventures. We reserve the right, without penalty, to make changes in the published itinerary whenever, in our judgment, conditions warrant, or if we deem it necessary for the comfort, convenience, or safety of participants, anything not mentioned in above program.