Fascinating Cyclades: 14-day sailing adventure amidst ancient monuments

Set sail on a fortnight-long cruise around the Cyclades and learn about their history, visit breathtaking sights, discover their secret corners. What not to miss? We will advise you!

The Cyclades have a lot to offer. This time we have prepared an itinerary that will be appreciated especially by history lovers, because the cruise will take you to the most beautiful monuments of history that the Cyclades hide.

Keep in mind that this is just inspiration for the cruise. Each itinerary must be planned with the current weather conditions and other factors in mind.

Itinerary: Alimos Marina – Cape sounion – Kythnos island – Milos Island – Sifnos Island – Paros Island – Mykonos Island – Delos Island – Syros Island – Andros Island – Kea Island
Difficulty: Experienced skipper
Lenght: two weeks route (288 nm total)

Before setting sail, however, consider your strength, as these are more challenging and longer routes that are suitable for more experienced sailors. Between July and August, you can encounter strong winds in the Aegean Sea that can make skippers struggle. However, if you manage to tame the wind, you will certainly enjoy a more adrenaline-fuelled sail on the waves!

Day 1: Sounion Cap (25 nm)

The cruise starts in the port of Athens – Alimos marina. The first night is spent at Cape Sounion. Nearby is the Temple of Poseidon, which you can visit.  It can be reached in just 5 minutes from the port if you take a local taxi.

Legend has it that King Aegeus jumped off a cliff here to end his life when he saw his son's ships with their sails stretched taut, returning from Crete. He mistakenly believed his son had been killed by the Minotaur.

Although the harbour is still full of life, it is large enough that you don't have to worry about anchoring. Plus, it's well protected from the northerly winds. However, beware of winds coming from the south or east, which the harbour is not protected from.

Temple of Poseidon.

Temple of Poseidon

Day 2: Kythnos Island (25 nm)

The next day, set a course southeast towards the island of Kythnos. The northerly winds that characterise the Aegean in summer will come in handy this time.

Don't miss the bay of Kolona, which offers mountainous water and invites you to swim. Afterwards, anchor in the port of Merihas, but be cautious when anchoring and stay away from the dock.

Sights to visit include the ancient agora of Kythnos, which was only discovered in 2009 and is estimated to be over 2000 years old.

The oldest finds date back to the 10th century BC. Most of them were everyday objects, religious statuettes made of pottery, marble and coins.

Another site that can be visited is near the port of Merihas. It is the torso of an ancient temple that was excavated during earlier archaeological excavations.

YACHTING.COM TIP: What to do when the northern wind, called meltemi, accompanies you on your journey? We have prepared an article for you!

You can also head to the northeast side of the island. This is Maroulas Bay (Loutra). You can go there by sea by boat or by land by taxi or bus. The bay is well protected from the melt (north wind).

Archaeologists have found the foundations of houses and various objects here. The oldest date from the Mesolithic period.

It is a very specific monument, the only one of its kind.

The island also boasts many caves that hide intricate labyrinths and interesting stalactites.

The largest cave, Katafiki, is located in the village of Driopida on the southern part of the island. It is so large that in the past it was used by the inhabitants as a shelter from pirates.

In the village you can also visit the Byzantine Museum and the Folklore Museum (both located in Driopida).

YACHTING:COM TIP: Learn to predict the weather based on clouds. We will advise you on how to do it!

Day 3: Milos Island (40 nm)

The following day, head south towards the island of Milos. Due to the location of your destination, the northerly winds of the meltemi should again make your journey easier. You can anchor in the main port of Adamantas.

 On the island you can admire the remains of the ancient city of Filakopi, which was one of the most important centres of the area in the past. People have lived here since about 3000 BC. Around 1 100 BC, the site developed into a commercial centre thanks to obsidian, and the city began to flourish.

In the village of Plaka, the main village of the island, you will find a museum which, among other things, offers visitors a view of a replica of the famous "Venus of Milos".

The sight of the exposed volcanic cave of Sykia on Milos Island.

The sight of the exposed volcanic cave of Sykia on Milos Island.

You can also explore the historical dwelling of Klima, which served as the island's initial port during ancient times. You can also view remnants of the ancient and Roman temples. It is important to keep in mind that the renowned "Venus of Milos" sculpture was unearthed in Klima.

Nearby is the ancient Roman theatre, which was first built in the 3rd century BC. If you have time, you can see a play or attend one of the concerts that are held here.

Milos also contains one of the oldest monuments of the Christian faith. It is the catacombs, which are located near the village of Tripiti. It includes extensive labyrinths and tombs.

In Adamantas, the main port of Milos, you can admire examples of the mining museum. Moreover, you can easily dock at the port and admire the beauty of the place. Visit Kleftiko, Gerontas, Gerakas or Sarakiniko beach.
If you decide to spend the night in the harbour, keep in mind that the wind can make the night uncomfortable with meltemi, which the harbour is not very well protected from.

View of the Adamantas Harbor.

View of the Adamantas Harbor.

Day 4: Sifnos Island (25 nm)

Next we will go to Vathi Bay in Sifnos island. Although it offers a safe anchorage, still beware of the wind meltemi.

Sights worth visiting include the ancient towers that were built on the mountain outcrops before AD, the Mycenaean walls, the 16th century Taxiarchis Monastery or the museum in the village of Kastro on the eastern side of the island. Since the island was inhabited 5,000 years ago, it is an archaeologist's paradise and the history of the island has a lot to tell. One of the most important sites is the Agios Andreas Hill site.

Day 5–6: Paros Island (30 nm)

To experience all the attractions conveniently, it is best to dock your vessel at the primary harbor of Paroikia. 

Paros also has many other anchorages. The channel between Paros and Antiparos is one of the most popular. The bottom in these places is mostly sandy and you can anchor here without any difficulties. However, you should bear in mind that the bottom is quite shallow!

The Paroikia harbor boasts a museum and a must-see temple called Delion, constructed in the 5th century and devoted to Apollo, offering an outlook of Delos Island. Also in close proximity is a temple of Artemis. For a historical adventure, head to Agia Anna hill and explore the remnants of Asclipoi's temple.

You can also visit the Valley of the Butterflies. It is a natural park located in Paros Island, Greece. The park is known for its abundance of colorful butterflies that fly around the lush green valley. Visitors can stroll along the shaded pathways and observe the beautiful creatures in their natural habitat.

To complete your itinerary, make sure to visit the Panagia Ekatontapiliani church, also known as the "church of the Virgin Mary with a hundred gates". According to tradition, the Byzantine emperor Constantine, who was the first Christian emperor, built the church. It's an important historical and religious site that's definitely worth a visit.

Day 7–8: Mykonos Island (35 nm)

Your next stop will be the island of Mykonos. The island's architecture is characterized by its charming white-washed buildings with blue accents, narrow winding streets, and small churches with colorful domes. Mykonos is also renowned for its lively nightlife scene, with a range of bars, clubs, and restaurants that cater to different tastes and budgets.

The island is dotted with several monuments and landmarks that are a testament to its rich history and culture. One of the most famous monuments is the Windmills of Mykonos, which are iconic structures that have become a symbol of the island. Another notable monument is the Church of Panagia Paraportiani, a whitewashed church that stands out for its unique design and is considered one of the most photographed churches in Greece.

We recommend staying on Mykonos for at least two days to give you enough time to explore the island and to take in all the ancient sites in peace. While the harbour at Mykonos Town is a popular spot, Ornos is also a great choice for anchoring due to its picturesque location in the bay and protection from strong northerly winds, especially during the meltemi season.

Keep in mind, however, that Mykonos is known as the island of the winds. The route can be more challenging and you need to be prepared for headwinds.

Church of Panagia Paraportiani

Church of Panagia Paraportiani

Day 9: Delos Island

Your next stop is small Greek island located near Mykonos that holds great historical and archaeological significance – Delos. It is believed to be the birthplace of the Greek gods Apollo and Artemis and was once a thriving center of commerce and culture in ancient Greece. Today, Delos is an important UNESCO World Heritage Site, home to well-preserved ruins of ancient temples, houses, and public buildings. Visitors can explore the island's rich history and admire its stunning architecture while taking in breathtaking views of the Aegean Sea.

To visit Delos, it's recommended to take a small boat from Mykonos since anchoring in Delos is prohibited without a special permit. 

Day 10-11: Syros Island (40 nm)

Syros is a small Greek island located in the Cyclades group. The island's main town, Ermoupoli, is a maze of cobblestone streets lined with colorful buildings, small shops, and cafes. Syros is also home to some of the most beautiful beaches in the Aegean, such as Galissas and Kini, which offer crystal-clear waters and excellent facilities. Additionally, Syros hosts several cultural events throughout the year, including the Syros International Film Festival and the Syros Jazz Festival, making it a great destination for culture enthusiasts.

Touring Ermoupolis is a fascinating experience, with notable sites such as the town hall, opera house, and the "Vaporia" district. For a stunning view of the deep blue sea, visitors can take a walk up the high hill of Ermoupolis to the old churches and monasteries of Ano Syros. Another recommended destination is the village of "Poseidonia" near the Phoinikas port, where visitors can see neoclassical aristocratic houses that reflect the island's past wealth and prosperity.

The small port of Phoinikas on the southwest coast of Syros is a recommended location to anchor as it offers good protection from the northern winds. From there, you can easily reach the island's main sites and the charming town of Ermoupolis using buses or taxis.

An expansive bird's-eye view of the beach and harbor of Finikas on Syros Island.

An expansive bird's-eye view of the beach and harbor of Finikas on Syros Island.

Day 12-13: Andros Island (38 nm)

The island boasts a diverse landscape that includes verdant hills, fertile valleys, and breathtaking beaches. You can explore picturesque villages, traditional churches, and historic landmarks such as the impressive Kastro fortress. Andros is also known for its museums, including the Museum of Modern Art and the Archaeological Museum, which display a range of artifacts and artworks that showcase the island's cultural heritage.

A noteworthy site to explore on Andros is also the Saint Peter Tower, constructed from local slate stone in the 3rd or 4th century BC, and situated in close proximity to the Gavrion port.

There are limited options for anchoring in Andros, primarily at the ports of Mpatsi and Gavrion, with the latter serving as the island's main port and providing excellent shelter. While Mpatsi is situated on the south side of the island, it is somewhat vulnerable to strong gusts, making it a less secure option. However, both ports offer convenient access to the main historical sites on the island, which can be reached by bus or taxi.

The Saint Peter Tower, an ancient and historic structure.

The Saint Peter Tower, an ancient and historic structure.

Day 14: Kea Island (30 nm)

Kea Island, also known as Tzia, is a beautiful destination that combines traditional Cycladic architecture with stunning beaches and natural landscapes. One of the island's main attractions is the ancient city of Karthea, which features impressive ruins including the remains of a temple, a theater, and a cobbled street. You can also enjoy hiking trails that lead to secluded beaches, picturesque villages, and hilltop churches with panoramic views.

Vourkari harbor is suggested as a safe anchorage spot for all types of winds. It is possible to either anchor or stay docked there. Close to Vourkari, you can find the Santa Eirini area, which is one of the oldest settlements in the Aegean, dating back to the 3rd millennium BC. In the island's capital of Ioulida, which is about 7-8 km from Vourkari, you can visit the Archaeological Museum of Kea and observe important ancient artifacts, including parts of Minoan-style sculptures.

After enjoying the final moments of sunshine and exploring historical landmarks, make your way to the Alimos port (12 nm) to conclude your unforgettable journey.

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.

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