Frequently Asked QuestionsAbout usOur Yachts
020 8004 3003 
Make an enquiryCheck availability

Seamaster » Destinations » Sailing in Greece » Dodecanese Islands » Dodecanese 14 Day Sailing Rhodes

Dodecanese 14 Day Itinerary - Rhodes 

Day 1 – Rhodes Marina

The largest of the Dodecanese Islands, Rhodes is abundant in beaches, wooded valleys and ancient history. Whether you seek the buzz of nightlife and beaches, diving in crystal-clear water or a culture-vulture journey through past civilisations, it’s all here. The atmospheric and UNESCO listed old town of Rhodes is a maze of cobbled streets spiriting you back to the days of the Byzantine Empire and beyond.


Day 2 – Ano Symi (Symi Island)

Symi is another quiet relaxing island which provides a chance to explore the natural paths, and fantastic landscapes this region of Greece has to offer. In Ano Symi you'll find a couple of bars and tavernas offering delicious traditional meals. We'd also recommend that you sample some of the local wine. 

Day 3 – Mandraki (Nisiros Island)

Mandraki is the main port of Nisiros and is one of the biggest settlements on the island. Its lovely traditional layout and whitewashed houses give it a very characteristic Greek feel. Around the village you'll find a variety of historical sites including the Paleokastro, an old fortress and an the remains of an ancient city which dates back to the 4th century BC. Alongside all of the historical sites you'll find a wide choice of tavernas and lively bars.

Day 4 – Kalymnos (Kalymnos Island)

Day 5 – Lipsi (Leipsoi Island)

Lipsi is one of the smaller islands in the Dodecanese. Tourism hasn't really touched this island giving it a very authentic Greek feel. There is a very which brings people from nearby Leros but it remains a very quiet and relaxing island. You'll find beautiful beaches with crystal clear water dotted around the coast. The small village of Lipsi does have a few shops and tavernas but we don't recommend going there to stock up.



Day 6 – Skala (Patmos Island)

Skala is the focal point of Patmos island acting as the main port and town. The charming settlement is built around the port and grew rapidly in the 19th century when a large number of wealthy families settled on the island. We'd recommend you explore the ruins of an ancient acropolis and the Church of Agia Paraskevi.

Day 7 – Arki (Arkoi Island)

Arki and its neighbour Marathi are around eight kilometeres from the coast of Patmos. Day boats from Patmos are the main source of tourism of the islands. The main bay offers good protection from strong winds and is a popular place to shelter for yachtsmen. You'll find one of two tavernas offering fresh fish that have been caught by the locals the night before.

Day 8 – Pythagorion (Samos Island)

As the name suggests the village owes its name to the famous mathematician Pythagorus. This charming little village is one of the most picturesque on Samos. Well preserved house, narrow pathways, cafes and restaurants all come together to make the village a well-known tourist destination.

Day 9 – Mikro Chorio (Agathonisi Island)

Agathonisi island is the most northern island in the Dodecanese area, The surface is rocky but does have some wild bushes and olive trees. Fresh water is scarce and is collected by wells and a boat which brings containers over for the locals. The island was regularly attacked by pirates and so the main settlement (Megalo Chorio) was built so it isn't visible from the sea. As you would expect provisions and tavernas are scarce but you will find a few in the main villages.

Day 10 – Lakki (Leros Island)

Lakki is the main port of Leros and also happens to be one of the largest in the Mediterranean, but don't let that put you off. Alongside the facilities you will find beautiful neoclassical buildings, white washed houses and wide pine tree lined streets. An impressive war museum is located close to the port and there is a wide choice of restaurants and bars.




Day 11 – Pserimos (Pserimos Island)

Pserimos is a tiny little village with only 35 people living on the island all year round. The island is heavily reliant on tourism. It is a charming little stop and offers an insight into what it would be like to live on a tiny remote island with only boats to get around on. Kos and Kalymnos are both relatively close if you need anything outside of the ordinary.




Day 12 – Kos Town (Kos Island)

Kos is the third largest island in the group, and the second most popular, after Rhodes. Soaked in history and ruins, after a few hours wandering Kos town’s fortress and the Asklepion (Hippocrates' ancient sanatorium), you become almost blasé at sidestepping millenia-old Corinthian columns gathering weeds at the roadside. The marina is purposed built and shouldn't be confused with the ferry port which is a few minutes north of the marina.

Day 13 – Livadia (Tilos Island)

Livadia is a beautiful little settlement with 300 inhabitants most of whom are involved with farming and tourism. The port is located seven kilometers south east of Megalo Chorio which is the capital of the island. The locals are very religious which is enforced by the number of churches surrounding the village. If you feel like being more adventurous you will be able to track down ruins of ancient castles dotted around.

Day 14 – Rhodes Town (Rhodes Island)

If you didn't get a chance on your first night we strongly recommend you take the time to explore the city of Rhodes. This stunning place is divided into two parts, the 'old city' and the 'new city'. The old city is surrounded by huge walls and is ones of the biggest and best preserved medieval settlements in Europe. Some of the highlights include the Palace of the Grand Master, the hospital of the knights and the inns used by the knights are all well worth a visit. If that isn't you cup of tea then the new city has a massive choice of lively bars and renowned night clubs.


Discount from your next holiday
When you subscribe to our monthly newsletter
You can unsubscribe at any time. Terms & conditions apply.