Two-week cruise around the Dodecanese islands

Sailing the Cyclades offers a perfect blend of crystal-clear waters, idyllic beaches, vibrant nightlife, and fascinating ancient history.

The Dodecanese islands are a group of 15 larger and 150 smaller Greek islands located in the southeastern Aegean Sea. A cruise around the Dodecanese islands offers a unique opportunity to explore some of Greece's most beautiful and unspoiled destinations, each with its own distinct character and charm.

Itinerary: Rhodes – Simi Island– Nisiros – Kos – Pserimos – Leros – Lipsi – Patmos – Leros – Kalimnos – Nisiros – Tilos – Halki - Rhodes
Difficulty: medium
Lenght: a two-week trip (270 nm)

In the summer months of July and August, the winds tend to increase in strength, but they are still much gentler compared to the main Aegean Sea.

Day 1: Rhodes

Rhodes is a stunning Greek island located in the Aegean Sea, known for its gorgeous beaches and ancient landmarks. Whether you're interested in history, culture, or nature, there are plenty of highlights to discover during your visit to Rhodes.

One of the top attractions on the island is the medieval old town, which is a UNESCO World Heritage Site. Here, you can explore the ancient fortifications, historic buildings, and narrow streets that date back to the Middle Ages. The Palace of the Grand Master of the Knights of Rhodes is also a must-visit site, offering visitors the chance to step inside a medieval castle that has been restored and converted into a museum.

Waterfall in the Valley of Butterflies.

Waterfall in the Valley of Butterflies.

If you're a nature lover, the Valley of the Butterflies is a popular destination that you won't want to miss. During the summer months, thousands of butterflies migrate to the area, making for a truly spectacular sight. And of course, with its beautiful beaches and crystal-clear waters, Rhodes is the perfect place to relax and soak up the Mediterranean sunshine.

Overall, Rhodes is a fascinating destination that offers something for everyone. Whether you're interested in history, nature, or just want to unwind on the beach, this beautiful island is sure to impress.

In the morning, you can head out to one of these places, enjoy a delicious lunch at one of the local restaurants, and then set out for the island of Simi.

Day 2: Simi Island (22 nm)

Simi is a small Greek island located in the Aegean Sea, near the coast of Turkey. In case of stronger winds, it is better to stay close to the Turkish coast.

The island is known for its stunning architecture, which features pastel-colored houses and neoclassical buildings. You can explore picturesque villages, visit historic monasteries and churches, and enjoy swimming and snorkeling in the crystal-clear waters of the Aegean Sea.

You can anchor either in the bay of Panormitis or venture further (14 nm) to the main port of the island. It is therefore necessary to plan your journey carefully to ensure you always arrive before nightfall.

Day 3: Nisiros (34 nm)

Sailing to Nisiros and its volcano is an unforgettable experience that you won't want to miss. As you approach the island, you'll be struck by its rugged, volcanic landscape and stunning beaches. Once on shore, hiking up to the crater of the island's active volcano is a must-do, offering breathtaking panoramic views. And after a day of exploring, you can unwind on a secluded beach and enjoy fresh seafood at a local taverna. Don't forget your camera - this is a trip you'll want to capture and remember forever.

YACHTING.COM TIP: Taking over a boat without worries! Take a look at what to pay attention to and how to do it.

Day 4: Kos (22 nm)

Sailing to the old port of Kos is a must-do for any sailing enthusiast. Upon arrival, you'll be greeted with stunning views of the medieval castle and the impressive Hellenistic ruins of the ancient city. Exploring the old port by foot is an adventure in itself, with hidden alleyways, charming cafes and quaint shops waiting to be discovered. Don't miss the chance to visit the iconic Plane Tree of Hippocrates, said to have been planted by the father of modern medicine himself. Sailing to Kos' old port is an experience you won't forget, offering a perfect blend of history, culture, and natural beauty.

The tree of Hippocrates.

The tree of Hippocrates.

Day 5: Pserimos (10 nm)

Pserimos is a small island off the coast of Kos, Greece, offering an untouched paradise for those seeking tranquility and natural beauty. It is perfect for swimming, sunbathing, and watersports. You can also explore the island's quaint village, sample delicious local cuisine, and experience the island's unique culture.

Day 6: Leros (30 nm)

Sailing to Leros is an experience like no other, offering a tranquil escape from the bustling tourist crowds. The island is a hidden gem, with crystal-clear waters and secluded beaches that are perfect for swimming and sunbathing. You can explore the island's rich history, from ancient ruins to the impressive castle overlooking the harbor. The island's laid-back atmosphere, delicious local cuisine, and friendly locals make it a must-visit destination for any sailing enthusiast looking to unwind and soak up the beauty of Greece.

We recommend anchoring in Agia Marina. The castle is located nearby, and you can explore the beauty of the town and enjoy the nightlife.

 The view of Agia Marina in Leros.

The view of Agia Marina in Leros.

Day 7: Lipsi (12 nm)

Crystal-clear waters of the Aegean Sea and the gentle breeze make it an ideal destination. The island's picturesque harbor provides excellent shelter and easy access to the town's amenities. The island's unspoiled beaches, charming villages, and authentic tavernas offer a taste of traditional Greek island life. A highlight of the trip is the opportunity to explore the nearby islets, including the uninhabited islet of Makronisi, which boasts a magnificent cave.

Day 8: Patmos

If you like, you can also stop by Aspronissia, which is an islet located northeast of Lipsi. However, it requires a lot of attention when approaching due to the shallow waters. If you decide to visit Aspronissia first, the distance will be as much as 20 nm. You'll need to go an extra five miles to reach Aspronissia and then return to the port of Lipsi before continuing on to Patmos. When you arrive, you can berth in the port of Skala, which provides all the necessary facilities.

YACHTING.COM TIP: Get ready for the Meltemi. We have written an article for you so that this northern wind won't catch you off guard.

Day 9: Leros (20 nm)

It's time to begin the journey back. You'll be revisiting some of the destinations, starting with the island of Leros.

You will sail south towards the west coast of Leros and berth in the port of Laki. There will be a relatively big marina in Laki with plenty of spots to anchor, as well as numerous bays around it where you can stay anchored.

A view of the magnificent island of Leros.

A view of the magnificent island of Leros.

Day 10: Kalimnos (20 nm)

Upon your arrival, you will dock your boat at the charming Emporios Bay situated on the northwest coast of the island. This serene location boasts breathtaking sunsets, providing a peaceful and relaxing atmosphere for you to enjoy.

Day 11: Nisiros (30 nm)

You find yourself back on the island of Nisiros. This presents an ideal opportunity for you to experience everything you missed last time. Alternatively, you can spend the day swimming and relaxing. You can anchor in the port of Paloi to replenish your supplies.

Day 12: Tilos (25 nm)

Next, you will head to the island of Tilos. We recommend leaving early as the local port is small and you may not find a free spot in the evening. If this happens, you can anchor in the bay of Livadia, which is well protected from northerly winds.

Day 13: Halki (17 nm)

Sailing from Tilos to Halki is a picturesque journey. The route offers stunning views of the Aegean Sea and surrounding islands. As you depart Tilos, you'll pass through the Tilos Marine Park, home to a diverse range of marine life. The tranquil waters and mild winds make for a smooth sail. Upon reaching Halki, you'll be greeted by the charming port town and crystal-clear waters perfect for swimming and snorkeling.

Day 14: Rhodes

On the last day, you will arrive back on Rhodes. You will have to say goodbye to the ship and head out to enjoy the last moments of your trip in the city!

Reminder: The information given (distances, mooring details, etc.) is for information purposes only and cannot be relied upon completely. Please study the nautical chart before sailing to ensure a safe and enjoyable voyage.

If you require any assistance or have further inquiries, please do not hesitate to reach out to us.

FAQs about Sailing around the Cyclades