Greek Islands Gulet Cruise & Hike #2
Southern Dodecanese

We meet at 1:00 PM for a welcome lunch (our office is available for luggage storage if needed). By 3:00 PM, we board our traditional all-wood, two-masted gulet. A 2.5-hour cruise takes us to Knidos, a stunning ancient Greek city dating back to the 5th century B.C. We step ashore for a scenic sunset hike to the lighthouse and through the remarkable ruins before returning for a delicious dinner on board. The Hike: 4kms/2.5mi, elevation gain and loss, negligible. Duration: 90 minutes. Overnight: Knidos. Included: Lunch & Dinner

Wake up to a refreshing swim, followed by breakfast on board as we cruise to Datça (Turkey) (2.5 hrs). Enjoy a leisurely stroll through this charming town before clearing customs and crossing into Greece. We sail to Symi Island, where we anchor in a peaceful bay for a swim and lunch while our agents handle customs. In the afternoon, a gentle coastal walk leads us to Irene’s traditional 18th-century home, where we roll up our sleeves for a fun, hands-on Greek cooking class. Expect generous pours of olive oil and plenty of laughs! After a home-cooked feast, we take a short evening stroll back to the boat. The Hike: Afternoon: 3.5 km (2.2 mi), 70 m (250 ft) elevation gain. Evening: 2.5 km (1.5 mi), negligible elevation.  Overnight: Symi Island Included: Breakfast, Lunch & Dinner

By now, you are getting used to a blissful rhythm: an early swim, a leisurely breakfast with a view, and then it’s time to head out on another beautiful walk. This morning, after a 40-minute cruise, we hike through a fragrant pine forest to Panormitis Monastery. One of the most important and atmospheric pilgrimage sites in the Dodecanese, the monastery sits at the head of a serene, fjord-like bay on the quiet southern side of Symi. Founded in the 18th century, the complex is instantly recognizable by its elegant Venetian-style bell tower and harmonious blend of monastic buildings arranged around a central courtyard. Inside the church is the famed icon of Archangel Michael Panormitis, believed by many Greeks to be miraculous and deeply protective—sailors in particular have long entrusted their voyages to him. Afterward, we enjoy a short cruise to a secluded cove with time to swim, paddleboard, or kayak, followed by a relaxed lunch on board. In the afternoon, an ancient flagstone path leads us from a deserted beach into Symi Town, a postcard-perfect harbor lined with colorful neoclassical mansions. Once in decline after World War II, Symi has been lovingly restored and now buzzes with life, from elegant homes to inviting tavernas. There’s time to explore at your own pace before we rejoin the gulet and cruise on to a spectacular anchorage, where sheer cliffs rise some 500 feet straight out of the sea. The Hike: Morning: 3.2 km (2 mi), 100 m (320 ft) elevation gain/loss (1 hr). Afternoon: 5.2 km (3.1 mi), 290 m (930 ft) elevation gain/loss (2.5 hrs). Overnight: Giorgios Bay. Included: Breakfast, Lunch & Dinner

We cruise for 3 hours to Chalki Island, one of Greece’s smallest inhabited islands. At Kania Beach, a morning swim sets the tone for the day before we hike into Chalki’s wild, barren interior—a landscape of ancient stone walls and abandoned farmsteads. Our reward? A stunning fjord-like bay with crystal-clear sapphire waters where our boat and lunch await. Later, we cruise into Chalki’s postcard-perfect port, where those keen for more adventure can climb to the 13th-century Castle of Saint John. The panoramic 360-degree views are worth the effort! The Hike: Morning: 5.4 km (3.2 mi), 260 m (850 ft) elevation gain/loss (2 hrs) Afternoon: 7.5 kms/4.7mi. Elevation gain 300 m/960 ft. Duration 2.5 hours. Almost entirely on paved road or flagstone paths. Overnight: Chalki Island harbor.  Included: Breakfast, Lunch & Dinner

This morning’s breakfast cruise brings us to Tilos Island, where we step ashore to hike along ancient coastal trails to Mikro Chorio, a ghostly village abandoned in the 1950s. Surrounded by centuries-old olive, walnut, and carob trees, we descend to Livadia Village for lunch at a beachside taverna. In the afternoon, those who want a challenge can tackle an ancient stone trail leading to a remote, abandoned settlement before returning to the boat for dinner on board. The Hike: Morning: 7.9 km (5 mi), 310 m (990 ft) elevation gain/loss (3 hrs) Afternoon: 5.6 km (3.5 mi), 195 m (620 ft) elevation gain/loss (2 hrs) Overnight: Tilos Island Included: Breakfast, Lunch & Dinner

A sunrise swim starts the day before we cruise to Nisyros, one of the Aegean’s most dramatic volcanic islands. A scenic drive takes us to the whitewashed village of Nikia, perched on the rim of the volcano. From here, we hike down into the caldera, following ancient trails from Homeric times. We end in Emborios, a stunning village with sweeping island views. We are picked up here by our private mini-bus and returned to the port, where we board the gulet and have a short cruise to Antonios Island for a swim and lunch. We return to Mandraki, Nisyros' colorful main town, to walk through its whitewashed lanes to a path that climbs gently up through olive groves to a colossal Doric fortress overlooking the sea. We return to the village for an exceptional dinner at one of Nisyros’s finest fish restaurants, where impeccably fresh seafood, thoughtful cooking, and a relaxed island setting come together for a truly memorable evening. The Hike: Morning: 7.2 km (4.5 mi), 320 m (1,020 ft) elevation gain/loss (2.5-3 hrs) Afternoon: 5 km (3 mi), 110 m (240 ft) elevation gain/loss (1.5 hrs) Overnight: Nisyros Island Included: Breakfast, Lunch & Dinner

This morning, we have a 3-hour cruise to Kos, where you have time to explore its rich blend of Greek, Ottoman, and Italian influences while we clear customs. We will have a swim and lunch anchored in the lee of Black Island before a final one-hour cruise brings us back to Bodrum, Turkey, where you can soak in the bustling harbor, shop for souvenirs, or savor one last bite of baklava before a farewell dinner on board.  Overnight: Bodrum Harbor tied up at the jetty so you can come and go as you please. Included: Breakfast, Lunch & Dinner

Disembark this morning for flights from Bodrum airport or the ferry to Kos. Since we are tied up to the jetty, you can depart anytime you like before 09:00 when we must disembark. We can arrange transfers from the boat even for very early flights. 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.  

For those who have already enjoyed our Turkish gulet adventure, this journey will feel familiar—and refreshingly different. In both Turkey and the Southern Dodecanese we travel by traditional gulet, one of the most relaxed and enjoyable ways to explore the Aegean. Days unfold at an easy rhythm: wonderful food, plenty of time to stretch out on deck with a cold drink, sunset views from the water, and the irresistible pleasure of slipping into the warm sea before breakfast.

What sets the Greek version apart is the setting and the flavor. Here, we often moor right beside small, postcard-perfect Greek villages, inviting evening strolls along harbors lined with fishing boats and cafés. To fully immerse you in local life, we head ashore frequently for lunches and dinners in family-run tavernas, where the cooking is simple, fresh, and seriously good.

The hikes follow a similar pattern to Turkey: we are dropped off by boat, walk beautiful coastal and island trails, and are picked up again at the far end. As always, the crew strikes that perfect balance—professional, friendly, and quietly taking care of everything—so all you need to do is enjoy the scenery, the walks, and the very Greek pleasure of slowing down and savoring the moment.