Classy 8-Day Cyclades Yacht Charter Itinerary: Unspoiled Islands

Day 1: Lavrion to Kea — Quiet Beaches & Island History

Start your Cyclades adventure with a short sail from Lavrio to Kea, the greenest and closest island to Athens. This route allows time for a pre-boarding visit to the Acropolis or Plaka if arriving early via Athens Airport.

Once anchored, enjoy Kea’s calm charm — from secluded Orkos Beach to elegant dining at To Spiti Sti Hora with sunset views and live jazz. Explore Ioulida, the island’s hilltop capital, home to a medieval castle and archaeological museum.

Offshore lies a hidden wonder: the wreck of the Britannic, Titanic’s sister ship, now resting 120 meters deep. Though inaccessible to recreational divers, it adds a layer of intrigue to your first night in the Cyclades.

Day 2: Kea to Antiparos

This is the longest cruising day for your yacht charter, approximately 50 miles, so prepare to spend a half day (or night) at sea. During June and September, dolphin pods are very likely to accompany sailors for part of the way.

Less than a mile off the coast of cosmopolitan, busy Paros, is a secluded retreat, the unspoiled island of Antiparos. The island has always attracted the interest of “alternative” tourists, who would rather be close to the natural beauty.

One of the many interesting sights is the cave of Antiparos, which extends at several levels with amazing limestone stalactites and stalagmites. It has been visited, among others, by Lord Byron, who inscribed his name on a wall, and is now fully renovated with steps, lighting, and cameras.

Another tiny island of Antiparos is Saliagos, the most ancient settlement in the Cyclades, now uninhabited and waiting to be discovered by your yacht charter.

Important Information:

The port of Antiparos is extremely small, but you can drop anchor anywhere around it (as long as you avoid the ferry route connecting the islands with Paros).

Don’t Miss:

• The Venetian Castle, now in ancient ruins, comes up in the middle of Chora. It was square in shape and had houses around it, while a circular tower was built in the middle. The entrance to the castle is next to the Cathedral of Agios Nikolaos.
• Despotiko island is located to the southwest of Antiparos and has some nice sandy beaches. Excavations in the wider region have shown that it was a religious cult center from the 7th century B.C. till the Roman Ancient Times.

Day 3. Antiparos to Folegandros

A favorite place of hippies and nature lovers in the 60s and 70s, Folegandros remains one of the hidden gems for stylish tourism and yachts in the Cyclades.
Chora, the island’s capital, featured the Kastro (Castle), a settlement built in the medieval style and inhabited without interruption to the present day.

Hidden among the houses are a few exceptional restaurants offering traditional fine dining and a chance to sample the wine-making culture.

The cave of Chrysospilia is reachable by yacht charter and was inhabited in antiquity; a testament to this fact is the plethora of ancient graffiti on the walls of the cave, as well as remains of pottery and cisterns. The graffiti are the names of young boys who visited the cave for a coming-of-age ceremony.

Important Information:

There are quite a few protected anchorages around the islands, the main one is the harbor of Karavostasis, not rich in amenities, but with the only refueling station on the small island.

Don’t Miss:

The unique Folegandros Ecomuseum, a complex of old buildings on a hilltop, is preserved to showcase the history of life in Greek Islands from antiquity to the present, with exhibits from daily life, agriculture, and animal husbandry among others.

Day 4: Folegandros to Kimolos

Another short haul back towards the common luxury yacht charter in the Greece area of Milos, and onto the sister island of Kimolos (Greek for “chalk”, a name whose origin is easily apparent by the white chalk hills).

The island’s main village is Chorio (Greek for “village” and seldom was a name more suited to the place!), up on a hill overlooking the sea, with extremely picturesque traditional architecture and a selection of museums (including the Folk and Maritime Museum).

Even in the island’s only port (and sole organized berthing facility), Psathi, there are secluded, almost private restaurants and tavernas offering a Greek culinary feast.

Important Information:

Kimolos is a very small island of less than a thousand inhabitants, and distances within it are very short. To move about from the port to Chorio there is a solitary bus and a few taxis for hire, but it is also within walking distance, for anyone in reasonable shape.

Don’t Miss:

The chance to sail your boat around the nearby tiny, uninhabited islands of Polyaigos, Agios Efstathios, and Agios Georgios, far from the crowds and providing a classic example of yacht charter in style around the Aegean sea.

Day 5. Kimolos to Sifnos

Next and after a short yacht sail, is the Sifnos (one of the larger islands), with a peaceful and relaxed atmosphere that makes it a popular destination among families and couples.

Sifnos is the ancestral island of Nikolaos Tselementes, author of the first Greek cookbook in 1932, his name becoming the generic name for any culinary guide since.

Interestingly, in Artemonas, near the capital Apollonia, there is an open-air cinema, one of the few remaining in Greece, where one can enjoy classic films under the starry sky, with free entrance.

Near Vathi, a horse riding operation is a wonderful opportunity to explore the island’s many trails and come closer to nature alongside these wonderful, therapeutic animals.

Important Information:

The most protected anchorages are the main port Kamares (which is usually very busy) and Vathi on the southwest side of the island, not as crowded, but secure from all winds due to its “omega” shape.

Don’t Miss:

• The traditional settlement of Kastro with the Church of Seven Martyrs at its entrance and its myriad of narrow alleys flanked by white-washed traditional Cycladic houses, hidden among which are a couple of cozy, relaxing cafes and bars.
• Open-air cinema, one of the few remaining in Greece

Day 6. Sifnos to Serifos

Serifos, northwest of Sifnos, is a bare and rocky island, its hills slashed by gorges; its highest point is Mount Tourlos, with 483 m.

The majority of Serifos beaches are secluded and perfect for total privacy, with soft sand, crystal clear water, and a relaxing ambiance. A few, such as Sikamia and Lia Beach, are nudist-friendly.

At Ano Chora (the upper part of Serifos), there are a few hilltop cafes offering traditional local cuisine and drinks, and further north lies the organic Chrysoloras winery, where small quantities of exquisite local wine may be tasted in many bars.

Important Information:

The main anchorage is Livadi/ Serifos, which features a newly built marina with abundant berths, protecting boats from most winds.

Don’t Miss:

• The picturesque Pano Piazza Square, in Chora, hovers on the side of a mountain, overlooking the large harbor.
• Also, the Old Mines, used to extract iron ore and now abandoned, have been providing an important income to the inhabitants of the island from antiquity up to 1964, when they were shut.

Day 7. Serifos to Kythnos

Kythnos is one of the hidden gems of the Greek Aegean, an island of abundant sunshine, traditional architecture, and friendly, hospitable people.

Chora (the capital), Driopida, and Loutra (with its therapeutic thermal springs) are the island’s main settlements, full of corners and alleys embellished with flowers, whitewashed houses, traditional taverns, windmills, and fountains.

Many of the island’s 90 beaches are still inaccessible by road, providing a haven for yachts and travellers who wish privacy, peace, and quiet.

Important Information:

• The safest places to berth are Merichas (the island’s main port) and Loutra with its makeshift but efficient marina, protecting boats from the Meltemi, the summer wind.
• As Kythnos is very close to Athens, it’s a popular city break destination in many itineraries and can be quite crowded during weekends.

Don’t Miss:

• The opportunity to discover scuba diving at Loutra, where the local dive resort is one of the best in Greece, run by a master of the sport.
• At Agios Dimitrios, a yoga retreat, Fykiada, promises a relaxing class through movement and light.

Day 8. Kythnos to Athens (Lavrio)

On the return journey, sailing your yacht off from Kythnos, it’s a long-ish (26 miles) sail to Lavrion.

It is perhaps a good idea to have a stop at a place where charter yachts rarely, if ever, stop, mainly because it is not considered a tourist attraction in the classic sense: the island of Makronissos (literally translated as “long island” due to its shape) has been officially declared an archaeological site in its entirety.

During the refugee crisis of 1922, it served as a quarantine station for Greeks arriving from Asia Minor, and during the civil war and its aftermath (1947-1958), it was an infamous internment camp/ place of exile, whose buildings still stand, abandoned, a reminder of dark times for Greece.

Nevertheless, it is a beautiful island, typical of the Cyclades landscape, and barely inhabited. With fewer visitors and boats, there is a multitude of secluded beaches and bays for you to enjoy.

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