Sailing the Dodecanese Islands on a Sailo Yacht Charter

Explore the historic eastern seas of Greece with a sailing trip around this beautiful archipelago

Although you’re closer to Turkey than mainland Greece, the Dodecanese are still very much Greek islands. Meaning literally 12 islands in Greek, the islands are all close enough to explore with a Sailo Greece yacht charter. Linking the main hotspots like Rhodes, Kos, Kalymnos and Symi is a popular and relatively easy sailing route.

Although the Dodecanese islands are unmistakably Greek, they do have their own character, somewhat east meets west. After all, they sit on the doorstep of the Orient.

Being so close to Turkey means you might also have the opportunity to stop off in an exotic port. Although it’s recommended you’re careful when sailing close to the Turkish coast, you should be able to avoid any problems by flying a Turkish flag. If in doubt speak to your boat’s captain when organising your yacht charter in the Dodecanese islands.

If you’re looking for the best place for a sailing charter in the Greek islands, you'll find Sailo boat rentals in Kos and Rhodes private yacht charters.

Kos - Marina Kos

Kos Island


Kos is home to a huge selection of hotel resorts and vibrant nightlife. But away from the resorts and the main town, you’ll find plenty of secluded beaches to explore, all the way to the southernmost tip of the island.

Kos makes the perfect base for sailing the Dodecanese islands, stopping to splash in the shimmering blue seas and enjoy the delicious flavours of fishing villages across the archipelago. You’ll find plenty of yacht rentals in Kos, ideal for groups of friends or family holidays sailing the Greek islands with a yacht charter.



Rhodes old town is the largest medieval town in Europe and is a UNESCO heritage site, with plenty of tavernas for a sundowner. And if you want to party the night away then Faliraki beckons.

Away from the tourist centres of Rhodes, it’s easy to enjoy a sailing charter to find your own private beach. As one of the largest of the Greek islands you’ll find plenty of space to find your own quiet corner with your friends or family.

Sailo offers many options of sail and motor boats to charter in Rhodes, allowing you to choose your perfect sailing trip in the Dodecanese. 



A short hop from Kos is the sleepy island of Pserimos. This island is one of the few islands in Greece that has no vehicle traffic, so a trip here is mostly guaranteed to be a very sedate experience. Pserimos can be reached easily by chartered sailboat, and although there are ferries bringing visitors, once they leave you’ll find a very peaceful scene.

There are a few small tavernas in the main village, but other than that you’ll find empty beaches, quiet hills and walking trails with not a soul around, save for a few goats and maybe a shepherd watching his flock. Bliss!



Another perfect location for a sailing charter in the Dodecanese islands. Kalymnos is one of the best places for rock climbing in Greece. Home to the beautiful Esperidon fjord, a stunning natural feature, well known as a great dive site, Kalumnos is also known for its high quality of citrus fruit found in the surrounding valleys.

Although not quite as popular with tourists as Kos, you’ll still find plenty to do here, albeit much less boisterous. There are lively tavernas serving the freshest seafood and bars with incredible views across the Aegean sea.

Charter a yacht in Rhodes or Kos and head to Kalymnos as part of a sailing trip in the Dodecanese.



Quite possibly one of the most handsome of the Dodecanese islands, Symi is easily accessible on a sailing day trip from Rhodes. The main town features a stunning harbour with beautiful mansion houses overlooking the bay.

Symi’s craggy coastline is home to numerous protected bays, perfect for a stop in your yacht charter. Some of them are serviced by tavernas and sunshades, but there are many that are just little nooks in the islands coast. With plenty of places to swim and snorkel, enjoy the quiet pace of life on this beautiful island.

Find your perfect boat charter in Rhodes or Kos and sail to the beautiful island of Symi for a fantastic sailing adventure in the Dodecanese islands.

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