From Beaches to Castles on a Dodecanese Yacht Charter Itinerary

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Choosing a Dodecanese yacht charter offers a wide variety of experiences and attractions, from visiting the ruins of an abandoned village to exploring the craters of a volcano to relaxing on a secluded beach in the sun. The pleasant, Mediterranean climate makes it ideal for chartering a yacht, and the best times to visit range from late spring to early fall.  


As most of the islands are closer together, you can choose either sailing or motor yachts for your charter. Most itineraries will travel round trip from either Kos or Rhodes, going North to South or South to North. However, if traveling in July or August, North to South itineraries are preferable due to the Meltemi winds.

First Day: Kos to Kalymnos - 17 nautical miles

  • Approximate Travel Time on 12 Knot Motor Sailers, Gullets or (slow) Motor Yachts: 1 hr 30 min
  • Approximate Travel Time on a 20 Knot (fast) Motor Yacht: 1 hr

 

Kalymnos. Photo by @traceyandghost. Used with permission.

Near the main harbor, the Archaeological Museum of Kalymnos holds relics—including statues, ceramics, and jewelry—that tell the history of the island over many centuries. Less than two miles away, the ruins of the Chrysoheria Castle sit perched above the city, named after the gold coins that are supposedly under its foundation. However, if you’d rather lay out in the sun than wonder about buried treasure, Kalymnos’ best beaches are all along the west coast, where you’ll find resorts with local tavernas and music bars.

 

Second Day: Kalymnos to Nisyros - 32 nautical miles

  • Approximate Travel Time on 12 Knot Motor Sailers, Gullets or (slow) Motor Yachts: 2 hr 45 min
  • Approximate Travel Time on a 20 Knot (fast) Motor Yacht: 1 hr 45 min

 

Nisyros. Photo by @andy_kozlov. Used with permission.

As a volcanic island, the natural beauty of Nisyros is its primary draw. The best things to do here are outdoor activities—exploring the volcanic craters, bathing in the thermal springs, and driving a scooter along the coast. Most of the action happens in Mandraki, the capital, and port, where you’ll find plenty of museums, castles, and tavernas to keep you busy. Upon investigating some of the other tiny villages on the island, be sure to visit the Main Square of Nikia, a photogenic spot with white and blue buildings, a bell tower, and a view of the Mediterranean Sea.

 

Third Day: Nisyros to Tilos - 20 nautical miles

  • Approximate Travel Time on 12 Knot Motor Sailers, Gullets or (slow) Motor Yachts: 1 hr 45 min
  • Approximate Travel Time on a 20 Knot (fast) Motor Yacht: 1 hr

 

Livadhia, Tilos. Photo by: Kostas LimitsiosCC BY

With less than a thousand residents, you’ll have no trouble getting some privacy and relaxation on Tilos. There’s even an abandoned village on the island where you can still walk amongst the rocky houses and ruins. The entire island is a nature preserve and was also the first Mediterranean island to run entirely on renewable energy. As such, most of it is covered in mountains, except for the few small villages in the valleys and along the coast, making it ideal for day trips and hiking.


Fourth Day: Tilos to Halki - 18 nautical miles

  • Approximate Travel Time on 12 Knot Motor Sailers, Gullets or (slow) Motor Yachts: 1 hr 30 min
  • Approximate Travel Time on a 20 Knot (fast) Motor Yacht: 1 hr

 

Halki Island Port. Photo by: Enpatrais. CC BY

Despite its designation as the smallest, inhabited Dodecanese island, Halki has its own medieval castle with a few original frescos intact. Nevertheless, its seclusion and laid back vibe make it the perfect place to get away from it all. Stroll along the marina to one of the tavernas for fresh seafood during the day or have a cocktail or two during sunset on Pondamos Beach. In fact, during the warmest months, buses depart from the Emporio to the most accessible beaches on the island, allowing you to just relax and unwind on your own time.

 

Fifth Day: Halki to Rhodes - 34 nautical miles

  • Approximate Travel Time on 12 Knot Motor Sailers, Gullets or (slow) Motor Yachts: 3 hr
  • Approximate Travel Time on a 20 Knot (fast) Motor Yacht: 1 hr 45 min

 

Rhodes. Photo by: @kostasboukou. Used with permission.

Nicknamed the “Island of the Knights,” Rhodes has a timeless beauty due to its integration of old and new. Contemporary culture abounds here with modern art museums, an aquarium, and luxury resorts and casinos. However, Rhodes has a rich history centered around its Old Town area where you can visit a Medieval clock tower, the Palace of the Grand Master of the Knights of Rhodes, and the city’s stone wall, built in the 1300s. Archaeological sites like the Acropolis of Lindos and the Acropolis of Rhodes provide a window into the ancient civilizations that were thriving here long before it became easily accessible by yacht charter.

 

Sixth Day: Rhodes to Simi - 27 nautical miles

  • Approximate Travel Time on 12 Knot Motor Sailers, Gullets or (slow) Motor Yachts: 2 hr 15 min
  • Approximate Travel Time on a 20 Knot (fast) Motor Yacht: 1 hr 30 min

 

Simi, Greece. Photo by @andy_kozlov. Used with permission.

The first thing that you’ll notice upon arriving in Simi from Rhodes, are the colorful, boxy houses set against brilliant, blue-green waters. Saint Nicholas Beach has swimming, snorkeling, and sunbathing while charming, outdoor cafes and restaurants attract couples and families. However, amid all the modernizations, plenty of history still occupies the island. Simi’s main attractions are its castle (or Kastro), built upon ancient ruins, and an 18th-century monastery still in use by Greek Orthodox monks.

 

Seventh Day: Simi to Kos - 57 nautical miles

  • Approximate Travel Time on 12 Knot Motor Sailers, Gullets or (slow) Motor Yachts: 4 hr 45 min
  • Approximate Travel Time on a 20 Knot (fast) Motor Yacht: 2 hr

 

Kos. Photo by @globetrottertreasures. Used with permission.

As one of the largest of the Dodecanese Islands, Kos has undergone more development, and as a result, more tourism. With eight different Blue Flag beaches, it’s the perfect island to soak in the Mediterranean sun with a cocktail in hand. Kos Town has a plethora of restaurants and bars to sample, which are surrounded by historic ruins, landmarks, and museums. Wineries and wine tours are also popular things to do on Kos, as is sampling their “krasotyri,” or wine cheese. Enjoy the city before catching a late return flight back home.

 

Which island excited you the most? Kos, with its Blue Flag beaches and bumping nightlife? Nisyros with its volcanic crater?

Find your yacht and start your chartered journey today!