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Sailing in the Cyclades: the irresistible islands that make sailors happy

– 29 November 2023 – Sailing itineraries

Sailing itineraries

Sailing in the Cyclades: the irresistible islands that make sailors happy

A 7-day cruise exploring the Cyclades, departing from Paros and visiting Ios, Santorini, Naxos, Delos and Mykonos. It’s hard not to be captivated by these breathtaking landscapes and their tranquil atmospheres with a strong Mediterranean flavor.

The sea, exceptionally clear, and small villages scattered on the hills or nestled within bays, showcase the prevailing white hues of distinctive cubic houses and the cobalt blue of roofs and windows. The Cyclades archipelago is the epitome of Greek islands. An archipelago composed of around forty islands with a barren and rocky appearance, yet particularly fertile and green within, emerging from the Aegean Sea. Sailing is the best way to discover them one by one, enjoying the golden beaches overlooking the crystal-clear sea, solitary coves and marvelous cliffs. Sailors are in love with this area due to the Meltemi wind that sweeps through this region—a powerful gust that particularly intensifies across the islands, especially during the months of July and August.

Spending a few days sailing in these lands will allow you to return to traditional Greece. Whether it’s Santorini, Naxos or Mykonos, everywhere you will breathe in the splendor of their beautiful past, the small fishing ports and the irresistible charm of the Mediterranean lifestyle.


Day 1, Paros, Parikia

The embarkation point for this cruise is the bay of Parikia, located on the southwest side of Paros. The capital of the island, Parikia is a charming town with a classic Greek flavor, featuring low white houses adorned with vibrant bougainvillea (a plant with pink flowers), narrow and winding labyrinthine streets and a multitude of places for post-dinner gatherings, aperitifs, taverns and restaurants catering to all tastes, along with the unmistakable atmosphere that only the Cyclades can offer. Fun fact: one of the central scenes of the famous movie “Immature, the Journey,” entirely set on the island of Paros, was filmed right in the center of Parikia.

Near the port is the beach called “Livadia,” a stretch of golden sand mixed with small colorful pebbles. Known for its clean waters, the beach proudly holds the Blue Flag. Among the nearby places to visit is the Temple of Ekatontapiliani, one of the most important and well-preserved Early Christian monuments in Greece. There is also the Archaeological Museum, which houses collections of ancient and classical sculptures, as well as the Venetian castle built with columns from ancient temples on the imposing hill overlooking the port of Parikia.

Day 2, Paros, Parikia – Ios, 26 miles

On the morning of the second day, the course is set towards Ios, an island with a dual nature: that of aperitifs and beach parties in the Chora, a historic destination for young tourists from all over Europe, and the quiet and secluded villages in the interior surrounded by barren and arid yet very picturesque landscapes. Despite being a relatively small island, Ios boasts over thirty beaches, coves and inlets where one can drop anchor, almost all with an unspoiled appearance. These range from the lively Mylopotas beach to Magganar, a delightful bay formed by 5 sandy beaches with shallow waters. And then there’s Agios Theodoti Beach, where you can enjoy the most beautiful sunset in Ios, or Kalamos and Papa, two beaches on the eastern coast perfect for escaping the crowds. Also beautiful is the small beach of Papa, south of Kalamos, which can only be reached by boat.

Once you’ve visited the Chora with its winding alleys, white houses, windmills surrounding churches, the famous medieval castle and the Church of Panagia Gremiotissa, the best way to get to know the real Ios, the rural one, is to venture into the inland villages inhabited by shepherds and farmers with their sheep and donkeys. From Pirgos, the highest point of Ios, you can enjoy the most beautiful panoramic view of the island. The village of Plakotos is also interesting.



Day 3, Ios – Vlychada, Santorini, 25 miles

With a 25-mile sail, we reach Vlychada Beach, located at the southern tip of the island of Santorini, about 6 miles from the capital, Fira, and not far from Agios Georgios Beach. It’s hard to remain indifferent to its imposing cliffs of bright white pumice stone and the bizarre shapes created by wind erosion and salt spray. The unusual and lunar-like landscape has earned it the nickname ‘Moon Beach.’ We can find anchorage in the nearby small port or anchor in front of the beach since the shoreline, with small pebbles mixed with gray sand, is protected from the main winds and stretches for 800 meters. It will be a pleasure to enjoy its transparent waters and intense blue color.

Still in the beautiful bay, there is an ancient tavern, still original in stone and wood, where you can taste dishes of local tradition and fresh fish. It’s also an excellent location for a sunset aperitif, considered one of the best in Europe. Near Vlychada Beach, you can visit the Tomato Museum, dedicated to one of the island’s characteristic products, providing insights into the production of this vegetable known worldwide for its goodness.


Day 4, Vlychada, Santorini – Iraklia, 32 miles

We leave the moorings to reach a special destination. Iraklia, in fact, is absolute peace. The best place to moor is in the small harbor near Tourkopigado beach, located along the southeast coast of the island. The bay is nestled in a long and narrow horseshoe-shaped inlet formed by two low, arid hills. The waters are calm, transparent and protected. Equally charming are Livadi beach, from which you can see the nearby islands of Schinoussa and Venetiko and Alimia, which is a favorite among snorkeling enthusiasts. It is famous for the wreckage of a German seaplane sunk not far from the shore during World War II.

In addition, Iraklia offers two villages, Agios Georgios, the main port of the island, which looks like a handful of typical white and blue houses arranged in an amphitheater around a bay. And then there’s Panagia, also called “Pano Mera,” a rural village on the western side of the island at the foot of Papas Hill. Also worth seeing are the Merichas cliff, over 100 meters high, and the Agios Ioannis cave, an underground cavity that opens along the south coast of Iraklia, which, according to some scientists, descends below sea level and reaches the island of Ios.


Day 5, Iraklia – Naxos, 20 miles

With a beautiful fast navigation under the influence of the Meltemi wind, you reach Naxos, the largest and greenest island in the Cyclades. The eponymous city, with its beautiful promenade and recently renovated main port, is very welcoming and ideal for spending a pleasant evening. This is where we will stay. With its high mountains, fertile lands, pristine beaches, and spectacular views of the Aegean Sea, Naxos is a true feast for the eyes. Moreover, even today, the inhabitants wear their traditional clothes and live off the harvests of the land.

The island is also dotted with ancient churches, monasteries and Venetian castles that reflect its centuries-old history. Naxos is also famous for its cultural events and traditional festivals, such as the Naxos Festival, the Wine Festival and the Fishermen’s Festival, which will allow you to immerse yourself in the rich folk culture of this piece of Greece immersed in the sea. Alternatively, you can take a step back in time and wander through the winding streets of the old town. You will be amazed.


Day 6, Naxos – Delos – Mykonos, 28 miles

We resume our cruise and set course towards the island of Delos. A legendary birthplace of Apollo and Artemis, as well as an archaeological site of immeasurable value, second only to Delphi in importance, this piece of land offers emblematic places of Greek mythology. From the port, the majestic Sacred Way leads to the Sanctuary of Apollo, where temples and altars stand. To the north, there is the sacred lake with the famous Terrace of the Lions and the Agora of the Italians. Delos is considered a sacred place, frozen in time, partly because of a curious tradition stemming from an oracle’s response, stating that on the island, neither birth nor death is allowed. Currently, only archaeologists are permitted to stay overnight on the island.

Once back on board, we sail towards the center of the Cyclades. Here, Mykonos awaits us. Loved by party-goers from all over Europe, celebrities, the LGBTQ+ community and hipsters, Mykonos is a beautiful island where you can experience wild and transgressive nights. Its beach parties are nothing short of legendary. For years now, Mykonos has become a chic destination with a large number of design hotels and exclusive villas with pools featured in architecture magazines. But what mass tourism has not changed is the authentic beauty of its landscapes that will remain in your heart. Mykonos is an island where you can still be moved by a sunset, a stroll through the narrow streets of the capital, and the sight of boats entering and leaving the harbor. Its winding narrow streets, white houses with colored windows, blooming balconies and excellent traditional cuisine will win you over.


Day 7, Mykonos – Paroikia, Paros, 10 miles

On the last day of our cruise, the only thing left to do is to return to Parokia on the island of Paros. Along the way, it’s worth dropping anchor in the large bay of Naoussa to try fishing, go diving or just to enjoy the magnificent water temperature. Once the boat is moored, you can also visit the Panagia Ekatontapiliani, a famous Byzantine church that remains a landmark for ancient Greek culture to this day.


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