For this dream sailing itinerary, we dive in the beauty of the Dodecanese Island Group, resting in the southeastern Aegean Sea. Starting from the stunning island of Kos, this journey will bring you to peaceful beaches, breathtaking views and will reveal an entirely relaxing experience unlike any other. If you are looking for a serene sailing holiday itinerary that will let you unwind and enjoy that iconic Greek summer, this is the golden ticket.

With perfect weather, average temperatures between 22 and 30 degrees Celsius and steady winds, it is guaranteed you will have an excellent sailing experience. All you have to do is pack your summer clothes, bring a book and prepare for seven days under the sun, refreshing clear blue waves splashing at your feet and ultimate relaxation.

Day 1 – Kos

kos, greece, sailing itinerary

The sailing itinerary starts in Kos. Getting to Kos and beginning this journey is an easy task. The Kos International Airport has numerous flights daily from all over Europe. Furthermore, the Kos marina where your chartered boat will be awaiting you is just 30 minutes away with excellent transport connections. Moreover, once you arrive at the marina, you will be astonished at how beautiful, lively, and well equipped the marina is.

Feel free to start your sailing itinerary immediately upon arrival. However, if your flight arrives a peculiar time or you want to spend some time getting supplies for the trip and exploring the area, we would also recommend it. Kos has an abundance of white sandy beaches that you only see in movies and plenty of sights to explore. Ancient ruins included. So feel free to take your time and enjoy this place before starting this dream sailing holiday. The thriving nightlife scene, world-class restaurants, and vibrant traditional culture are definitely worth it.

Day 2 – From Kos to Vathi – 11NM

vathi, kalymnos island

We start this dreamy holiday with a place that has truly captured that traditional Greek atmosphere. Vathi is a fishing port situated on the island of Kalymnos. From fishing boats to bars and taverns, everything here has some sort of magical aura that transcends time. Furthermore, as the rest of the island is mountainous, the port has an unusual look with hills surrounding the village. Definitely a place worth exploring.

Day 3 – From Vathi to Lakki – 21NM

lakki, leros island

What a better place to visit next than another staple for the Dodecanese Islands. Lakki, on Leros Island, is another perfect example of a Greek sailing destination that has kept its traditional charm. An ideal place to witness that neoclassic whitewashed architecture we see everywhere in Greek postcards. Enjoy the pine lines streets and peaceful atmosphere and spent some time quality time here. There is plenty to do since Lakki is one of the largest ports of the Mediterranean. Scuba diving with the colorful fish? This place has one-upped the usual diving experience with the possibility to dive with shipwrecks from WWII. Now that is something unique.

Day 4 – From Lakki to Astypalaia – 43NM

astypalaia island

Day four of this dream sailing itinerary bring us to the island of Astypalaia. This island also has that classic whitewash architecture, but with a robust Cycladic influence. Blue doors, wooden balconies, and windmills follow the natural curve of the island and create a setting that is almost out of this world. This is where the Dodecanese meet the Cyclades and mix perfectly. Places, where you can anchor overnight here, are Skala and Perigialos. Small harbors that are usually quiet and offer access to water and electricity. Humble but truly serene and authentic.

Day 5 – From Astypalaia Island to Pali – 38NM

pali, nisyros island

More serenity awaits us in the cozy fishing village of Pali. An interesting fact is that this place, located on Nisyros Island is one of the Dodecanese’s oldest settlements. The town is surrounded by a natural bay, making it a beautiful place to moor, swim, or simply take in the beauty of the views. This is the ultimate place to visit the beach as it is incredibly picturesque with large sand dunes, waters as blue as the sky and therapeutic baths.

Day 6 – From Pali to Livadia – 18NM

livadia, greece

The next fantastic destination of this one-week sailing itinerary is the village of Livadia on the Island of Tilos with a population of around 300 cheerful and welcoming locals. From Livadia, you can easily access the close by the capital of Megalo Chorio famous for its stunning churches. Furthermore, castle ruins can be found dotted around the island and offer an exciting opportunity for an adventure. Besides, this is the home of many rare birds, an ecological park and over 4,000 species of flowers. Nature has really outdone itself here.

Day 7 – From Livadia to Kos – 35NM

kos, police station

Wow, now if that wasn’t the most relaxing summer holiday, we can’t think of anything that would be. The last day of the one-week sailing itinerary brings us back to Kos, now filled with beautiful memories. In case you didn’t give this place the deserved attention the first day, go ahead and do it now. Prolong this dreamy experience a bit more and enjoy the white sanded beaches, lush vegetation, and ancient monuments one last time.

We hope this sailing itinerary inspired you, and if you want more or you are longing to explore a different area of Greece, here are a few suggested itineraries:

So, what do you think? Does this one-week sailing itinerary from Kos and around the Dodecanese sound like the perfect route for you? We would love to hear what you think in the comments below or on our Facebook Page. And remember, if you need help with chartering a yacht, the Tubber Experts are always here to help!

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