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’ve settled into a lovely routine—morning swim, scenic breakfast, and then a gorgeous hike. At 9:00 AM, we embark on a hike through a scented pine forest to the Panormitis Monastery, which sits on the edge of a tranquil bay. We have a short cruise to a secluded cove were we enjoy time for swimming, stand-up paddleboarding, or kayaking, followed by lunch on board. This afternoon, an ancient flagstone path leads us from a deserted beach into Symi Town, a picturesque harbor lined with colorful neoclassical mansions. After WWII, Symi fell into decline, but today, beautifully restored homes and lively tavernas bring it back to life. We explore the village at leisure before enjoying a seafood feast at a waterfront taverna. 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: Symi Town. Included: Breakfast, Lunch & Dinner

We cruise 3 hours to Chalki Island, one of Greece’s smallest inhabited gems. 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, where we enjoy lunch at a charming taverna. Later, we cruise to Antonios Island for an evening swim and a magical sunset over Nisyros. The Hike: 7.2 km (4.5 mi), 320 m (1,020 ft) elevation gain/loss (2.5-3 hrs) Overnight: Antonios Island Included: Breakfast, Lunch & Dinner

We explore Mandraki, Nisyros' colorful main town, before hiking through olive groves to a colossal Doric fortress overlooking the sea. After returning to the boat, we sail 3 hours to Kos, where you have time to explore its rich blend of Greek, Ottoman, and Italian influences while we clear customs. 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. The Hike: 5 km (3 mi), 110 m (240 ft) elevation gain/loss (1.5 hrs) 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 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.

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.

1. We thus spend more time in villages, both to enjoy their charm but also because there are fewer secluded bays than in Turkey. We will have two nights out of seven in secluded anchorages, and five nights in charming harbors.
2. Dinners: we eat off the boat more often for dinner. Firstly, because we use a Turkish gulet and crew so we want to make sure you get a taste of the local cuisine. Secondly, it’s always fun to get out at night and mingle with the locals we meet along the way.

We can assure you that they are both fabulous tours.