Cyclades Islands Greece: 7-Day Charter Itinerary

Greek Islands, Church in Chora, Serifos

Cyclades Islands: Stunning and Sophisticated

The Greek Islands are legendary for their spectacular beauty, warm and welcoming people and remarkable history. The Cyclades comprise more than 220 islands. They are located in the heart of the South Aegean Sea. Legend attributes their origin to the Greek god Poseidon. He threw a handful of rocks onto the seabed. They took root and blossomed into islands. A luxury yacht charter through the Cyclades Islands will transport you to this world of myth, mystery and magnificence.

There are some 1,400 Greek islands, but just 227 are inhabited. This is a yachting paradise. On charter in the Greek islands you will experience lovely beaches, charming harbors, picturesque villages and amazing World Heritage sites. Here we explore the best of the Cyclades Islands.

Cyclades Islands Day 1: Athens – Kea

Kéa, also spelled Kéos, also called Tziá, is the westernmost of the Cyclades islands. It is located just 60km southeast of Athens. It is a popular getaway for Athenian yachtsmen due to its proximity and remote, unspoiled charm.

Cyclades Islands Greece, Ancient Coin from Kea
Ancient Coin from Kea

Kea, like most Greek islands, has a long history of occupation by numerous nations and cultures. The earliest excavated settlement, Ayia Irini, dates back to the Bronze Age. Later the Byzantine Empire brought prosperity. Later still, medieval Venetians witnessed economic decline. In 1566 it came under Turkish rule. The Turks ruled until 1912, when Kea joined the kingdom of Greece. These shifting eras of political control have left a rich cultural, archeological and architectural record.

Cyclades Islands, Cyclades Archipelago, Kea

Dock at the picturesque fishing hamlet of Vourkari. Take a 20 minute walk to the east of the village. You’ll find a large lion carved from the rock face. The cat is attributed to an Ionian sculptor from around 600 BC.

Taxi up to the Chora above Vourkari. The traditional hillside village of whitewashed houses offers scenic views. It’s a pleasant hike back down.

Cyclades Islands Day 2: Kea – Syros

Syros is a very trendy destination in the Cyclades Islands. Syros is the commercial, administrative and cultural center of the Cyclades Islands. There are excellent restaurants, galleries, shops, tavernas with live music, and a casino. Archaeological digs reveal artifacts from the Cycladic civilization, 2800 to 2300 BC.  During the 19th century, Syros was a wealthy and powerful port. Many neoclassical buildings and grand mansions from this era remain intact throughout the island.

Cyclades Islands Greece, Little Venice, Mykonos
Little Venice, Mykonos

Many will find it fortunate that tourism is not a major revenue source for Syros yet. However, more and more people are making it a destination. Expats and visitors alike appreciate the cultural authenticity and traditional island charm.

Cyclades Islands Day 3: Syros – Mykonos

Mykonos is the most famous tourist destination in the Cyclades Islands. It is a liberal island, LGBT friendly, with beautiful nude beaches and trendy all night discos. Here, locals and tourists mingle among the superyacht set, the jet set, artists and celebrities from all over the world.

This upscale island appeals to everyone with stylish resorts, beach clubs, fine restaurants and boutique shopping. There are also many museums and more than 70 Christian Greek Orthodox churches. In town, ancient winding alleys are a delight to poke around. They appear to have naturally emerged from the rock itself.

Cyclades Islands Greece, Old Port of Hora, Mikonos
Old Port of Hora, Mikonos

The cosmopolitan flavor, sophisticated tourist infrastructure and density of Mykonos is to be enjoyed. However, it is in unique contrast to other, more culturally authentic islands.

Cyclades Islands Day 4: Mykonos – Serifos

Serifos is known in the Cyclades Islands for its traditional villages and a few coastal resorts. It’s also famous for its unique cuisine. The harbor on Livadhi Bay hosts a ring of outdoor restaurants with delightful views. Patronize any one. They are equally ideal for sampling local wine and food.

Serifos has an intriguing history intertwined with mythology. Ancient and modern residents produce art and pottery, work gold and silver, and in modern history, iron ore. Chora, the quaint hilltop town above Livadhi Bay, has an eclectic Archeological Collection open Tuesday through Sunday.

Kastro is a  fascinating medieval village. It is built on top of a high cliff on the island’s northwestern shore. It is the site of the ancient city of Sifnos. Visit the fortified Monastery of the Taxiarchs, built in 1572. The sole monk, who has maintained the sanctuary since 1958, might still be around.

Greek Islands, Church in Chora, Serifos
Church in Chora, Serifos

Cyclades Islands Day 5: Serifos – Kythnos

Kythnos, the Island of Apollo, is serene and unspoiled despite its popularity with Greek tourists. Anchor in crystal clear water and sunbathe on white sand beaches.

Divers can explore shipwrecks, underwater caves, rock formations, coral and marine life at 32 different dive sites.

Take a healing plunge. The hot springs of Kythnos (Thermia) are located at the coastal village of Loutra. This ancient source of warm, sulfur water, is believed to have curative powers.

Take a hike, or a taxi. Picturesque hilltop villages, such as Chora and Driopida, are worth a visit, especially with a camera. You can also visit the ruins of a medieval citadel and town near Cape Kefalos.

Cyclades Islands Day 6: Kythnos – Athens

Greek Islands, Athens view of the Acropolis

Depart Kythnos bound for Athens. This is the final leg of your luxury yacht charter through the Cyclades Islands. Athens is a metropolis with fascinating archeological sites, museums, galleries, upscale boutiques and local handicraft stalls. Consider extending your charter with a land segment.

Many tourists visit the Acropolis and the old district of Plaka, nestled at the base of the ruins. Needless to say, it’s very touristy. Venture downtown Athens. There are some 100 museums. Be sure to see one or two. Athenians love theater. There are lots of those as well. Plus all the usual wonders found in any of the world’s major cities. Yet, while there’s no shortage of reasons to keep very busy, sometimes it’s fascinating to take a pause. Sit at one of the outdoor cafes that line the boulevard. Sip a Greek coffee. Watch the world pass by, just as the Greeks have done from time immemorial.

Cyclades Islands Day 7: Athens – Airport

Today you must disembark from you beautiful charter yacht. Farewell to your captain, crew and the breathtakingly beautiful Greek Islands. Time to start planning your next Greek Islands charter adventure!

Some of our favorite places:

Ioulis, Kea: To Spiti Sti Hora (The House in the Country) Restaurant, Eparchiaki Odos Ioulidas-Chavounon, Ioulis 84002. Beautiful place with fabulous vistas, great people, nice wine, and amazing food. 

Syros, Ermopouli: Apollo Theater was built for wealthy residents in 1861 as a small-scale version of Milan’s La Scala. Theater, opera and cultural events scheduled throughout the summer.

Mykonos, Chora: Kalita Restaurant, classic Greek flavors enriched with a modern touch under the supervision of our Chef, Vaios Ntoytsias.

Kythnos, Chora: Tratamento,  shop Owner Irini Pageneli makes traditional sweets and liquors, cakes, cheese pies and sells organic provisions.

Destination overview: Greece: Islands of Enchantment

Contact Select Yachts and let us match you with the perfect luxury yacht and crew. We’ve explored popular ports, toured the yachts and met the crews. Charter with us. We know the ropes.


Exotic Vacations Just on The Horizon!

We’ll get back to you faster than a headwind!

Charter Specials