The Cyclades are definitely the most well-known and popular complex of Greek islands with their characteristic blue and white house aesthetic. Located in the Aegean Sea, the Cyclades offer the best chance to discover sandy coves, taste the local delicacies, and indulge in the Greek sun. Here is where you’ll find the famous Santorini, the cosmopolitan Mykonos, and lesser-known gems such as Sikinos, and Koufonisia.

Yacht Charter Day 0 – Arrival in Athens

Athens is the ideal starting point for all sailing excursions to the Cyclades. To make the most of the opportunity, you can arrive a few days early and explore the best that Athens can offer. Don’t miss a walk around the Plaka neighborhood under the Acropolis and a visit to the Panathenaic Stadium, host to the opening and closing ceremonies of the first modern Olympics in 1896. The rooftop bars around Monastiraki offer great views of Acropolis Hill at sunset, and for shopping, you can try the elegant area of Kolonaki.

Athens - Monastiraki
Athens, Greece

Yacht Charter Day 1 – Athens (Alimos) – Kythnos

We start our day early and depart from Alimos Marina towards Cape Sounion, located only 69 km southeast of Athens. Cape Sounion is the southernmost tip of the Attica peninsula and is where the Temple of Poseidon stands high on the hill. A popular tourist attraction, the area offers travelers and locals a pleasant excursion from the city, with plenty of tavernas and other food establishments nearby to complete the scenery.

Cape Sounion has been an important symbol and area for sailors since ancient years. Poseidon was, after all, the god of the sea, and this is where people would gather to make animal sacrifices and offer gifts.

After passing by Cape Sounion, we set sail towards the island of Kythnos, only about 45km south. Kythnos is preferred by yacht charters both for its convenient location next to Athens but also for the more than 90 beaches on offer, most of which can only be visited by water. Kythnos has plenty of “must-see” attractions, including Kolona beach, a crescent-shaped sandy paradise, the natural thermal spring of Loutra, and one of the largest caves in Greece, Katafyki, that was discovered in the 1830s and was once used as a hiding place from the pirates.

Kythnos Greece Yacht Charters
Loutra Village, Kythnos

Yacht Charter Day 2 – Kythnos – Serifos – Milos

From Kythnos, we set sail for the island of Serifos, about 23 NM to the south.

The Hora, or main town of Serifos, is built amphitheatrically on top of a hill offering amazing views of the Aegean Sea below. Its laid-back, unpretentious vibe is one of the things that makes this destination so special to visitors. Only a few hours from Athens and other popular island destinations, it is an excellent option for island hopping, but it has managed to retain its traditions and unspoiled character.

If time allows, a visit to the Venetian castle built during the 15th century is recommended to enjoy the view. Bars, taverns, and restaurants line the pretty cobblestone streets for refreshments and options to dine.

It is true that Serifos has a little bit of everything, from its rich history to the food and of course the beaches. On the east side, don’t miss Lia, Ayios Sostis, Psili Ammos, Ayios Ioannis, and Platis Yialos. Options on the west side of the island include Ambeli, Vayia, Ganema, Koutalas, and Malliadiko, among others.

When passing by Platis Yialos, a visit to the church of Skopiani, with its characteristic blue and white dome is recommended.

Leaving the island of Serifos behind, for Milos, best known for its natural beauty, volcanic landscapes, and otherworldly beaches.

The volcanic geology of the island can be seen by the odd-shaped rocks and wonderful colors that make up its white-sand beaches.

Milos was famous for its rich abundance of natural resources and minerals even during ancient times, especially sulfur. One of the most ancient mines in the Mediterranean is found on the island.

Milos had managed to stay under the radar of most visitors until it catapulted into popularity for the beauty of Sarakiniko beach, with its unusual and impressive rock formations.

This is also where the statue of Aphrodite (Venus de Milo), housed in the British Museum, was found.

Milos Cyclades Greece Yacht Charters
Mandrakia Village, Milos

Yacht Charter Day 3 – Milos – Polyaigo – Folegandros

From Milos, we cruise towards Folegandros, another lesser-known gem of the Cyclades.

But not before making a stop at Polyaigo, meaning “many goats,” an uninhabited Greek island that is found between Milos and Kimolos.

The southern part of Polyaigo is where we’ll find spectacular beaches and plenty of caves where Mediterranean monk seals (Monachus monachus) find refuge. A great spot for a refreshing swim and snorkeling.

Arriving in Folegandros, visitors will land at the port in the small village of Karavostasis.

Named after the son of King Minos, ruler of Minoan Crete, and son of Zeus, Folegandros offers untouched beauty, beautiful cobalt waters, and a relaxing atmosphere.

Follow the twisting stone path from Hora to visit the Church of the Assumption of the Virgin Mary. According to tradition, the silver-plated icon of the Virgin Mary found here is miraculous. The path takes 15 minutes and offers incredible views of the area below.

In the village of Ano Mera, you can witness a traditional rural settlement built in the 19th century. The Folk Art museum that is open during the summer offers a glimpse into the traditional everyday life of people living here.

Another interesting place to visit is the cave of Chrysospilia. About 30m above sea level, this natural wonder dates back to the 4th century BC and features inscriptions with the names of ancient Greek names like Themistocles, Cleon, Callimachus, and Pythagoras. According to one theory, the cave could have been used as a worship site and initiation ceremonies for young men coming of age.

Folegandros Greek Island
Strolling around Folegandros | credit: Dimitra Galani via Unsplash

Yacht Charter Day 4 – Folegandros – Sikinos – Santorini

On Day 4, we leave Folegandros behind and prepare for one of the highlights of the trip and the most popular island in the Cyclades – Santorini!

But before we make it to Santorini, it is time to discover Sikinos.

Known as the island of Oinoe (meaning wine), Sikinos has not witnessed the same development as nearby islands but is content with being a place of rest and relaxation for travelers.

With two villages, Allopronia and Chora, Sikinos is the ideal spot to relish the small joys of life and connect with the local pulse. The Hora, or main town of the island, is split into two settlements, Castle and Chorio (meaning “village”). Here you will find a handful of tavernas serving local delicacies right next to the port.

The road network on the island is still under development, with only a handful of dirt roads connecting the settlements; they are, however, well maintained.

From Sikinos, we make our way south towards the island of love, sunsets, and volcanoes; that is Santorini!

Santorini, also known as Thera, is the largest island of a complex, including Thirasia, Nea Kameni, and Palea Kameni. The volcanic eruption in 1500 BC is what gave Santorini its distinctive half-moon shape after the middle part of the island sunk to the bottom. This is also why many still believe that Santorini is where Atlantis once stood.

While it is one of the most visited islands in the Aegean for yacht charters, Santorini is a challenging option in terms of anchorages. The depth of the caldera is more than 400m, making it impossible for most vessels to anchor here, and reef and shoal waters are common along its steep rocky shores. The newly built marina at Vlychada offers the safest option for cruisers.

You can’t visit Santorini without tasting the local wine and preferably touring some of the wineries in person to learn more about the local varieties and volcanic soil, which has played an important role in the economy of the island as well.

A walk through the main town of Thira for coffee or lunch while looking at the caldera and a sunset stroll in Oia (the more romantic version of Thira) is a must. Santorini doesn’t have to try when it comes to romance. If you are thinking of arranging a romantic or special dinner with your partner, this is the place to do so

Agali Beach Sikinos
Agali beach in Folegandros | credit: Canva Library

Yacht Charter Day 5 – Santorini – Ios – Amorgos

From Santorini, we head north towards Ios, a hilly island that is nestled between Sikinos and Iraklia.

Arriving at the port of Ios at Ormos on the northwest side of the island there is a flurry of activity during the summer months, but also plenty of secluded beaches and coves to retreat to.

The beauty of Ios is also why it frequently stars in film productions, including the movie Ginger and Cinnamon (Dillo con parole mie) and Big Blue (Le Grand Bleu), which was shot in Manganari, a picturesque white sand beach on the southernmost point of the island.

From the port, it is only a 15-minute walk to the main settlement of Chora. Here the white and blue Cycladic architecture dominates the scenery.

The rich history of the island is evident by the excavations on Sarkos Hill which brought to life a prehistoric settlement that played a key role as a trading route. An earthquake in 2300 BC forced people to evacuate, and the area was never resettled.

The island of Amorgos is the next stop on our Athens to Mykonos itinerary across the Cyclades. The easternmost island of the Cyclades, Amorgos, is closer to the Dodecanese complex of islands. The island has no airport, which means interested visitors will need to get the ferry from Athens or fly to Naxos and then ferry to reach their destination.

The port of the island, Katapola is the first village to discover on your visit before making your way to the ancient site where the remains of a Minoan city are located.

In recent years, Amorgos has also been recognized for its production of “Rakomelo” a traditional drink that dates back to ancient times as a treat for guests. This strong alcoholic drink is popular in all the Cyclades and the island of Crete.

Don’t miss a visit to the Monastery of Hozoviotissa dating back to the 11th-century, not far from the popular beach of Agia Anna. The walk down from the monastery to the beach takes approximately 40-minutes.

Unsplash - Santorini
Santorini Blue Domes, Cyclades

Yacht Charter Day 6 – Amorgos – Koufonisia – Paros

After Amorgos, we set sail towards the small islands of Koufonisia, packed between various other smaller islands and the setting of some of the most incredible azure waters in the Aegean.

Koufonisia consists of three main islands, Pano (Upper) Koufonisi, Kato (Lower) Koufonisi, and Keros. The latter, Keros, is uninhabited and an important archaeological site.

Chora is the main and only village in Koufonisia that provides some amenities to visitors and is located at Upper (Ano) Koufonisi. Kato Koufonisi spans an area of about 4.3 square kilometers and is almost uninhabited. Some of the best beaches are Foinikas, Loutro, Italida, Pori and Nero.

Leaving the secluded beauty of Koufonisia behind, we set sail towards Paros.

The marble of Paros was considered of the finest quality ever since antiquity and was used for the Temple of Solomon, the Venus de Milo, and the temples on Delos island.

Its main port, Parikia, is located on the western side of the island that features impressive neoclassical mansions and the 13th-century Venetian castle.

Another village worth visiting while on the island is Naoussa. Hundreds of fishing boats line this charming port, and visitors flock here to dine, shop, and stroll along the picturesque streets.

When it comes to beaches, there is something for everyone, with golden sand, secluded coves, and crystal clear waters. Next to Parikia, you’ll find Marchello, Parasporos, Livadia, and Krios beach. Santa Maria, Golden Beach, Punta, and of course, Kolymbithres are among the most popular options.

Naousa Village, Paros

Yacht Charter Day 7 – Paros – Delos – Rinia – Mykonos

As we leave Paros behind to make our way to our final stop, it would be a shame to miss the two islands of Delos and Rinia.

Excavations on Delos island have been ongoing since 1873, and it’s also a protected UNESCO World Heritage Site of immense archaeological significance. There have been no people living on the island since antiquity.

In the past, Delos served as one of the most important sanctuaries of the ancient world and was considered the birthplace of Greek gods Apollo and Artemis. Staying on the island overnight is prohibited, as is mooring within 500 meters of the island. Daily ferries depart Mykonos, Naxos, and Paros. Swimming and diving around the island is prohibited.

From here, a visit to Rinia or Rhenia is only a stone’s throw away, separated by Delos by a 100-meter wide channel. There is no ferry service to the island of Rhenia, which means you can only reach it on a private vessel. This is another uninhabited island, but contrary to nearby Delos, the population declined recently and was only abandoned in the 1980s.

Feeling rested and refreshed, we are ready to arrive in Mykonos, only a short 1-hour sail from Rinia. After parting ways, you are free to continue your trip and discover more of the island at your leisure.

Mykonos has been nicknamed the “Island of the Winds,” which justifies the presence of so many windmills. This charming island was once no different than nearby secluded spots on the Aegean. It rose in popularity during the 1960s after former US first lady Jackie Kennedy Onassis visited with her second husband, Greek tycoon Aristotle Onassis. Since then, Mykonos has become synonymous with luxury, opulence, exclusive parties, and Hollywood celebrities that come to enjoy the party scene and stunning beaches.

Little Venice is a popular spot for an evening drink or meal. Afterward, you can swing by the Windmills of Kato Mili, one of the most iconic sites on the island.

In terms of beaches, the south coast is where you’ll find the most popular options, such as Paraga, Platis Gialos, Paradise, and Super Paradise.

Mykonos, Greece, Cyclades

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