112,5 miles in total



DAY 3 – NISYROS TO TILOS – 19,6 miles

DAY 4/5 – TILOS TO SYMI – 27,7 miles

DAY 6 – SYMI TO RHODES – 23,9 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.



This is another small island, with only around 1,000 residents spread across just a few thousand square miles.

According to Greek mythology, Nisyros was created when the sea-god Poseidon tore off a piece of Kos Island and threw it at an escaping giant to block his path. It was mentioned by Homer in some of his writings and over the centuries it was inhabited by both Greek and Roman conquerors, before the Knights Hospitaller settled here in 1315.

This volcanic island has some of the best views in all of Greece, perfect for watching the sun rise and fall over mountainous terrain, and it’s very popular with day-trippers from Kos Island. We recommend renting a car and taking a trip around the island, enjoying as much of the scenery as you can and making regular stops to snap some Instagrammable pictures.

It’s a great place for hikers, if you’re into that sort of thing, but you don’t need to do a lot of climbing to see some breathtaking views and snap some equally breathtaking pictures. Just prepare a packed lunch, grab a few bottles of water, and enjoy your escapade.

It’s small enough that you won’t get lost, but big enough to sate your appetite for adventure.

The main attraction of Nisyros island (Greek Dodecanese archipelago) is the giant Stefanos volcanic crater – excellent trace of ancient volcanic eruption, still emanating of sulphur aroma and full of bubbling hot mineral springs. Stefanos crater has a diameter of 300 meters.


DAY 3 – NISYROS TO TILOS – 19,6 miles

The first leg of your adventure will take you to the neighboring island of Tilos. This island has a population of less than 1,000 at last count, and while it’s popular with tourists from Rhodes and other islands, it’s far from a tourist hotspot.

We recommend taking a walk through the ancient streets, snapping pictures in and around the ancient buildings, and enjoying a level of freedom and solitude that you rarely find on Greek islands.

Tilos is very much an undiscovered gem, and as you step off the boat you’ll get a feeling that you have the whole island to yourself.


DAY 4/5 – TILOS TO SYMI – 27,7 miles

Another island on your journey is Symi, an affluent, charming island that offers a little something for everyone.

If you still have some energy in your legs then we recommend climbing the several hundred steps of Kali Strata that will take you to the old town of Chora. It’s a trek, but the destination is well worth it. It’s a similar story with the Panormitis Monastery in that it’s a bit of a journey and one that is somewhat out of the way, but worth it when you get there.

You can rent a scooter in the town if you want to make this journey easier, but there’s plenty to see on foot if you’d rather walk. Whatever you do, make sure you’re back in town for lunch or an evening meal. We also recommend trying the local shrimps. Known as “Symi’s Shrimps”, these pan-fried bites are famous in this area and are a delicacy you won’t want to miss.

There are plenty of tavernas and bars on the island as well, including ones that offer a view of the Aegean sea. We recommend grabbing a seat outside one of these bars or restaurants in the evening, just in time to watch the sun go down on the island, and on your Greek adventure, as you sip an evening cocktail or a chilled ouzo.

If you’re in the town during the summer months then you may also catch the Symi festival. This festival has become a hotspot for Greek musicians since it was first founded in 1995. It could provide you with an opportunity to hear some local music and maybe even partake in some events yourself.


DAY 6 – SYMI TO RHODES – 23,9 miles

These are the final days of your trip and the end of your Greek adventure, but there is still more to see. If you only spent a few hours or a day in Rhodes, then we recommend booking yourself into a hotel when you arrive to the island and spending a couple more days there.

The Mitsis, Lindos Blu, and Boutique Hotel will all provide you with a top-of-the-line 5-star experience as you spend more time on the island. Try some of the fine dining restaurants like Alter Ego, Shark Fish or Mageirotechneio Paraga, visit the museums and sites around, purchase gifts and goodies at the local stores, and take some more pictures.

Rhodes is one of the biggest islands in Greece and by far the biggest of the Dodecanese islands. It is home to one of the biggest airports in Greece as well as five ports, and there are connections to the Greek mainland as well as many other major European cities.

Rhodes has been inhabited since the neolithic age and over 3,000 years ago it became home to the Minoan and then the Mycenaean civilizations, before participating in the famous Trojan war. Some traces of this ancient history remain on the island today, but mostly in its museums, with the oldest history you can actually explore dating back to around the 4th century BC.

One such historical site is the Acropolis of Rhodes, which is a short journey from the centre of the city of Rhodes and consists of a temple, theater and stadium. Most of it is in a state of ruin, but it’ll still give you some insight into the ancient history of this island and it’s a great appetizer to begin this cultural feast.

We’d also recommend taking a walk down the Street of the Knights for a piece of medieval Greek history and, if your schedule allows it, paying a visit to the Fort of St. Nicholas. There is also a lot of history outside of the city, including the ruins in Kamiros and the monastery in Lindos, but there’s a lot of traveling to come and a lot of things to see, so feel free to keep it local and within walking distance if you prefer.

Rhodes is a very tourist-centric island, so there are also plenty of beaches, bars, and fun activities for you to enjoy if you’re not in the mood for a history lesson.


up to 2 cabins/4 guests – 3000euro

up to 3 cabins/6 guests – 3750euro