120,4 miles in TOTAL


DAY2 – KALYMNOS TO LEROS – 19,5 miles

DAY3 – LEROS TO LIPSI – 12 miles

DAY4 – LIPSI TO PATMOS – 10,9 miles

DAY5 – PATMOS TO LEVITHA – 23,4 miles






Castle of Chora

Myrties Beach

Emporio Beach

Massouri village (for rock climbing)

The island of Kalymnos is the next stop on your Dodecanese adventure. In modern history, this island has been home to Venetian, French, Russian, Turkish, German and English conquerors. More so, certain rumors connect the island to the Mycenaean civilization thousands of years before any of these invaders arrived. It’s fair to say that this little gem in the Aegean Sea has been busy over past centuries. Now, it’s in its peaceful years, enjoying its retirement by welcoming thousands of visitors from neighboring islands and countries all over the world.

Visiting Kalymnos is a must for anyone taking a sailing voyage in the region. Not only is it one of the biggest islands in the Dodecanese, but it has some of the most beautiful ancient buildings and ruins you could hope to find.

One of these is the Castle of Chora, which sits atop a mountain at the highest point of the island, looming over the many hotels, houses, and shops below. As you stand below the imposing fortress walls and the sheer rock of the hillside, you’ll understand what it felt like to be a Venetian soldier or a soldier of an invading army tasked with conquering it over 700 years ago. Inside the castle walls, you’ll find ruins of houses where over 200 residents once lived and worked. There are also cannons overlooking the sea in search of pirates. Just outside the walls, you’ll see monasteries and churches.

Myrties and Emporio beaches are the most popular among travelers. Myrties Beach flanks the natural port, featuring verdant hills in its surrounding, pebbles and transparent waters. Emporio Beach, located in a bay, is a peaceful beach featuring pebbles, crystal-clear waters, and hilly surroundings. It offers plentiful options for sunbathing in peace.

The locals thrive on tourism, producing high-quality olive oil and honey. If you’re a fan of either of these Greek staples, then we’d definitely recommend picking up a few jars and bottles in town. Local honey and oil are among the freshest and purest you’ll find on your cruise and are perfect gifts to friends and family back home. Freshly-baked bread makes for a delicious snack back on the boat.

This island of the Dodecanese Archipelago is an excellent rock-climbing destination, with the best climbing spot located near the Massouri village.


DAY2 – KALYMNOS TO LEROS – 19,5 miles

Leros War Museum

Panteli Castle

Notable for sandy and pebble beaches and many ancient shipwrecks around the island, Leros is a first-class diving destination. The island features abundant vegetation and boasts tranquil coves and bays ideal for solitude seekers. If you wish to socialize with other travelers, you can do so at taverns and bars of many organized beaches. Leros is a mythical place where Artemis, the Greek goddess of the Hunt, hunted deer.

Leros had a turbulent history, and you can acquaint yourself with it at the Leros War Museum. There, you will learn the role of the island in the Peloponnese Wars, Greek Revolution and the Lybian War. Moreover, the museum elaborates times when the Macedonians of Alexandre the Great, Romans, Byzantines, Venetians, Genoese and the Turks ruled the island.  The main focus of the museum, though, is the Second World War. Initially, the island suffered from British bombs while being occupied by the Italians. Once Leros was taken by the Brits, the bombing continued, but this time by the Germans.

Dominating the island’s skyline and offering views of the island and the Aegean Sea, the Panteli Castle is a medieval Byzantine fortress that remained intact despite long periods of turmoil. You can reach the castle by walking or by bike from a nearby village. When you arrive, don’t miss the collection of ancient works of art exhibited in the Panteli.

Leros features a great dining scene. Koukouvades is a local specialty whose main ingredient is marinated fish. Chicken Souvlaki comprises skewered pieces of chicken meat, while Myzithra is a local version of cottage cheese. For premium dining, visit Sweet Leros 1897, a reputable eatery serving great food and outstanding desserts.


DAY3 – LEROS TO LIPSI – 12 miles

Monastery of St. John the Theologian

Kambos Beach

Lientou Beach

Elena Beach

The island of Lipsi (Leipsoi) features pure waters, intact nature and sandy beaches offering utmost tranquility and relaxation. However, it is the local cuisine that makes Lipsi standing out among other Dodecanese islands. Lipsi is a reputable wine-producing destination, while its wild thyme honey is among the best honeys in the world. Besides, the island has its own version of Myzithra cheese.

Local cuisine is a reason enough for visiting Lipsi Island, but visiting the Monastery of St. John the Theologian is another highlight you shouldn’t miss. The monastery safeguards icons hundreds of years old, and you can access the top of the complex to admire scenic views of the surroundings. Besides unparalleled views, the monastery boasts gilded chandeliers, old artwork and more.

Peaceful beaches dot the coastline of Lipsi, with Kambos, Lientou and Elena being the most popular among holidaymakers. Kambos is a long beach edged by a grove, while family-friendly Lientou is a pebble beach featuring calm, pure waters. Elena is a sandy beach featuring rocks, transparent waters and surroundings with undergrowth.

Lipsi Town is the top shopping destination on this tiny island. Aside from wine, cheese and honey, you may find interesting trinkets and presents in its shops. There is also a bicycle rental service operating in the town for anyone seeking an efficient and entertaining way of exploring the island.


DAY4 – LIPSI TO PATMOS – 10,9 miles

Skala Beach

Agriolivado Beach

Monastery of Saint John

Cave of Apocalypse

We’re in the middle of our sailing adventure, which means it’s the right time to relax, resupply and rejuvenate. Patmos is the perfect island for this since it’s a place for spiritual reflection as opposed to history, hedonism, and consumerism. Skala is the main port of Patmos.

This Dodecanese island has organized and pristine beaches, of which organized beaches of Skala and Agriolivado are the most famous ones. Renowned for its pure waters and soft sand, Skala Beach features sunbeds, parasols, and trees offering shade. Agriolivado, located at the base of elevated ground and surrounded with greenery, boasts calm waters, sand, and pebbles.

According to legend, Patmos is the island where the Book of Revelation originated, and today, it’s a pilgrimage destination for Christians from all over the world. The Book of Revelation is the last book in the Christian Bible, written by the disciple John after he had a vision. On Patmos, you can visit the cave in which this vision took place. Various churches and monasteries offer further spiritual experiences to devout believers.

The most significant religious complex of the island is the Monastery of Saint John (Agios Ioannis Theologos), occupying a vantage point above Chora, the capital of Patmos Island. Surrounded by high, crenelated walls and turrets, the monastery appears more like a fortress than a place of worship. Visit the library to see historical documents, manuscripts, and biographies of saints. The on-site museum exhibits items studded with precious stones, vestments, and holy relics.

Cave of Apocalypse, located between Chora and Skala, used to be home to Saint John. Measuring around 6.5 x 5.5 meters and occupied by a sanctuary, it is the place where the Book of Revelation originated.

Because of its exceptional tranquility unmatched by any other place in Greece, Forbes magazine awarded Patmos the title of “the most idyllic place to live in Europe.”


DAY5 – PATMOS TO LEVITHA – 23,4 miles

Outpost from the WWII

Levitha is the smallest island we explore during our trip, worth a visit for its rugged coastline abounding with coves, hiking options and the feel of complete solitude. While hiking, climb Levitha’s highest point to discover the outpost the Italians built during the Second World War. The population of the island is between four and five people (depending on whom you ask), but its waters abound with fishing boats and sailing yachts during the summer season.

Visit the restaurant run by the locals during summer and learn about the island from them. Levitha Island is great for hiking and rambling, and it’s also incredibly peaceful. As soon as you dock, you’ll get the impression that you and your group are the only people on the island, which makes for a great change if you’re used to the more tourist-centric islands like Kos, Rhodes, Crete, and Santorini.



On the final days, it’s time for some relaxation and contemplation. We are sailing to the first island back. You’ve seen ruins, fortifications and religious structures on seven different islands while walking, hiking, climbing and relaxing. It has been a fun-packed lesson in Greek history and culture.



Back to Bodrum/Turgutreis – TURKEY


up to 2 cabins/4 guests – 3000euro

up to 3 cabins/6 guests – 3750euro