Greek Islands Gulet Cruise & Hike #1
Northern Dodecanese

Our adventure begins in Bodrum, Turkey, a lively seaside town rich in history and easily reached via Istanbul or many European hubs. We gather at 13:00 for lunch in town (luggage storage is available at our office if needed), before boarding our boat around 15:00. A gentle two-hour cruise brings us to the sheltered waters off Catal Island, where you can enjoy your first swim in the warm Aegean Sea. Tonight, savor dinner on board beneath a canopy of stars. Overnight Catal Island. Lunch and dinner included. 

Start the day with a refreshing swim before breakfast on deck—fresh fruit, creamy yogurt, and other local treats. We disembark in Turgutreis to clear Turkish customs, then cruise to Kalymnos, where we enter Greece via its lively little port. Our hike begins through whitewashed lanes and follows a historic military track built by the Italians in the 1920s. The trail climbs over a ridge with sweeping sea views before descending into the picturesque village of Rina, tucked at the end of a narrow inlet. After a swim, we return to the boat for lunch and a leisurely afternoon cruise along Kalymnos’ dramatic west coast, where towering limestone cliffs lure rock climbers from around the world. In the late afternoon, we disembark at Emborious Bay for a sunset hike—or, if you prefer, a relaxing sundowner on the beach. Dinner tonight is in the lush garden of a lively, family-run taverna.  The hike: 8.5 kms/5.2 mi, 410 m/1,300 ft elevation gain and loss. Duration 3 hours in the morning. Optional late afternoon hike: 4 km/2.5 mi, 130m/400ft elevation gain and loss. Duration 1.15 hours. Overnight Kalymnos Island. All meals included.

The day begins much like yesterday—with a refreshing swim and breakfast on deck as we cruise to the island of Leros. Our hike traces the quiet coastline, then winds inland past farms and whitewashed chapels before descending into a shaded gully that shelters a WWII Italian bunker system, now an engaging museum recounting the 1943 battle between German paratroopers and Allied forces. From here, a further 40-minute walk brings us to Lakki harbor, a striking architectural “time capsule.” Once an Italian military base, the town’s Art Deco and Modernist buildings offer a surprising glimpse of Fascist-era design. We rejoin our boat here for lunch and a swim in a secluded bay before setting out on a late-afternoon hike to the island’s medieval castle. After taking in the sweeping views, we descend into the village for a cool drink, followed by dinner ashore at one of the finest restaurants in the Aegean. The Hike: 9 kms/5.6 mi. Elevation gain and loss 140m/400ft, Duration 2.5 hours. Afternoon hike: 3 kms/1.9 mi Elevation gain and loss 140 m/400 ft. Duration: 1 hour. Overnight Leros Island. All meals included.

Another relaxed morning begins with a swim in the clear Aegean, followed by a hearty breakfast as we motor toward tiny Lipsi Island—legendary home of the sea nymph Calypso, who, according to myth, held Odysseus here under her spell for seven years. We land in the island’s main village (the only inhabited spot) and set off on a walk to the Five Martyrs’ Monastery before crossing to the far side, a wild and untouched landscape. Our trail descends to the beach, where we reunite with our boat and cruise to a quiet anchorage beside a deserted island. Dinner is served on board beneath the stars. The Hike: 9.7 kms/ 6 mi, Elevation gain and loss 230 m/730 ft. Duration 3.5 hours. Overnight Lipsi Island. All meals included

We set out early this morning, cruising to Patmos and landing at Psili Amos Beach. From here, our hike follows the coast to Grikos Bay for a coffee break before ascending to Chora, the island’s ancient capital. Crowned by the Monastery of Saint John, this UNESCO World Heritage site is a maze of narrow whitewashed lanes, tiny chapels, and clustered houses that seem to lean against the monastery’s formidable walls. After lunch in the village, we descend to the island’s west side, where a deserted beach awaits and our boat is ready to meet us. A scenic cruise around Grikos Bay sets the stage for dinner on board. The Hike: 7.3 kms/4.6 mi. Elevation gain and loss 280 m/900 ft. Duration 2.5 hours. Optional extension of 5 kims/3 mi Elevation gain 150m/480ft. Duration 1.5 hours. Overnight Patmos Island. All meals included

This morning offers an optional hike back up to Chora, this time approaching from the east and looping down to the harbor village of Skala. You’ll have some free time to wander before we set sail in the afternoon for Leros. A late-day walk along the island’s wild northern coast brings us to the chapel of Agios Isidoros, perched at the end of a slender isthmus in a serene bay. We moor on the island’s western side, perfectly placed to enjoy a stunning sunset before dinner on board. The Hike:  4.5 kms/2.8 mi. Elevation gain and loss 230 m/740 ft. Duration 2 hours. Overnight Leros Island. All meals included

This morning we cruise to the eastern side of mountainous Kalymnos for a hike to a vast cave, where stalactites and stalagmites are revealed through a narrow opening. The trail winds across the hillside before descending to the idyllic bay of Palionisos—perfect for a swim, a cold beer, or both. From here, we clear Greek customs and cruise back to Turkey, arriving in Turgutreis before continuing on to Bodrum. Our boat ties up beneath the mighty walls of the 13th-century Crusader castle. There’s time to soak up the lively atmosphere of Bodrum before gathering for dinner on board in the sheltered yacht harbor. Overnight in Bodrum. The Hike: 5 kms/3 mi. Elevation gaina nd loss: 200m/640ft. Duration 1.5 hours. All meals included

Your adventure concludes this morning after breakfast. With the boat moored in Bodrum harbor, you can disembark directly—even for early flights. Final disembarkation is by 09:30. From here, you may fly out of Bodrum, or take the 9:15 ferry to Kos (arriving at 9:45) and connect to Athens with flights departing after 13:00. Alternatively, you might choose to overnight in Kos and fly out the following day.  Early breakfast included.

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 the weather.