We have a "Day Zero" on this tour because you will likely want to arrive this evening either on Kos Island (Greece), in Bodrum (Turkey), or in Athens or Istanbul to be close for the tour's start tomorrow. This will depend on where we pick up the boat and that will depend on your tour departure date. Regardless of the date, let us know where you'd like to stay, and we'll happily recommend and book hotels for you. We will send you a "Pre-departure" document with details. Overnight not included.

Depending on the departure, the tour departs either from Kos Island, Greece, or Bodrum, Turkey (It depends on the boat we are able to charter). Both are well connected by air to their national hub (Athens or Istanbul) as well as frequent flights to European hubs. Assuming that we start from Kos: Kos is the second largest island of the Dodecanese after Rhodes and has a rich history that is reflected in its architecture and historic monuments. It was the birthplace of Hippocrates, the “Father of Western Medicine,” and was an important city in both Greek and Ancient Roman times. The harbor is guarded by an 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. There’s plenty to explore for a day or two! We meet today at 1 pm for lunch and then board the yacht at 4 pm at the lastest. A 1-hour cruise takes us to the tiny island of Pserimos, where we drop anchor in an idyllic little bay for a swim before dinner. Overnight Pserimos Island. Dinner included.

Kalymnos Island
Begin your day with a refreshing swim, then breakfast on deck, featuring fresh fruit, creamy Greek yogurt, and other local delights. We cruise to Kalymnos island where we drop off in its busy little port. The hike leads you through the town's whitewashed houses to leave on a historic military track built by the Italians in the 1920s. We’ll ascend over a ridge with stunning sea views before descending into the picturesque village of Rina, nestled at the end of a narrow inlet. After a swim and lunch, we’ll set off on an afternoon hike that takes us past ancient ruins and up to a cliff offering dramatic vistas over the island. A short van ride brings us to Emborious Bay, where we’ll rejoin our boat. This evening, enjoy a delightful dinner in the garden of a vibrant, family-run taverna—an unforgettable end to a day filled with adventure. Hiking: 2.5 hours in the morning, 2 hours in the afternoon. Overnight Kalymnos Island. All meals included.

Leros Island
This morning echoes yesterday’s, with a morning swim followed by breakfast while cruising to another island: Leros. The hike takes us along the deserted coastline and then gradually inland past farms and white-washed chapels before descending into a forested gully with a WWII Italian bunker system. It is now an interesting museum about the 1943 battle for the island fought by German paratroopers and Allied troops. A further 40-minute hike brings us to Lakki harbor, a fascinating architectural “time capsule.” It was originally an Italian military base built during the Fascist period, so is an unexpected and striking tribute to Art Deco and Modernist Italian architecture. Our boat meets us here, and we have lunch on board, then enjoy a swim in a quiet bay before embarking on a late afternoon hike up to the medieval castle that dominates the island. Drop down into the village to enjoy a cold drink before dinner, which we have on shore this evening at one of the best restaurants in the whole of the Aegean. Hiking time: 3 hours in the morning, 1.5 hours in the afternoon. Overnight Leros Island. All meals included.

Lipsi Island
Another relaxed morning awaits you, with a lovely morning swim followed by a hearty breakfast as we motor to the next island. Disembark on tiny Lipsi Island, where, according to myth, Odysseus was held for 7 years under a spell of the sea nymph Calypso. Disembark at the main village (the only human habitation on the island!) and begin a hike to the Five Martyrs’ Monastery and over to the other side of the island, which is completely wild and uninhabited. Descend to the beach to rejoin your floating home, which will take us to a quiet bay in the lee of a deserted island. Dinner on board. Hiking time 3 hours. Overnight Lipsi Island. All meals included.

Patmos Island
We leave early this morning to cruise to Patmos Island and are dropped off at Psili Amos beach. From there we hike to Grikos Bay for a coffee break before climbing up to Chora, the island’s ancient capital and home to the Monastery of Saint John. A UNESCO World Heritage site, the village is a labyrinth of narrow whitewashed alleys, small row-houses, and chapels huddled beneath the massive walls of the monastery. Stop for lunch in the village and then head down to the west side of the island to a deserted beach where we meet our boat. Cruise Grikos Bay and then enjoy dinner on board. Hiking time 2.5 hours in the morning, and 2 hours in the afternoon. Overnight Patmos Island. All meals included.

Leros Island
We have an optional morning hike back up to Chora, but this time from the east side, with a loop back down to Skala. You’ll have free time in the village and then an afternoon cruise to Leros Island, where we take a late afternoon hike along the wild northern coast to end at the lovely chapel of Isidorus, which sits at the end of a narrow isthmus in a secluded bay. Our mooring on the western side of the island affords us a gorgeous sunset before dinner on board. Hiking time is 2 hours in the morning, and 2 hours in the afternoon. Overnight Leros Island. All meals included.

We have a morning cruise to the east side of mountainous Kalymnos Island, where we have a hike up to an enormous cave, whose stalagmites and stalactites can be seen through a narrow opening. The tiny trail traverses the hillside and eventually leads down to beautiful Palionisos Bay, where we can enjoy a cold beer, or a swim, or both. Have lunch here before boarding the gulet and cruising to Pserimos Island. There is an optional late afternoon hike before dinner on board. Hiking time 2.5 hours in the morning, plus optional one hour in the afternoon. Overnight Kos harbor, or Bodrum harbor, depending on the departure. All meals included

Your adventure concludes this morning after breakfast. We will be tied to the dock in either Kos or Bodrum harbor (depending on the departure) so you can depart directly from the boat this morning, even for very early flights. We must disembark no later than 09:30. Breakfast included.

Please note: 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.