Classy 8-day Cyclades Yacht Charter Itinerary – Explore Greek Islands in Serenity!

Yacht Charter Day 1 – Athens (Lavrio) to Kea

Yacht Charter Day 2 – Kea to Antiparos

Yacht Charter Day 3 – Antiparos to Folegandros

Yacht Charter Day 4 – Folegandros to Kimolos

Yacht Charter Day 5 – Kimolos to Sifnos

Yacht Charter Day 6 – Sifnos to Serifos

Yacht Charter Day 7 – Serifos to Kythnos

Yacht Charter Day 8 – Kythnos to Athens (Lavrio)

Classy Cyclades Sailing Itinerary

This is the alternative itinerary, a classical “classy” trip to the Cyclades, merging a virtual visit to ancient Greece with a classic yacht charter getaway. The itinerary focuses on a traditional journey in nature; with a dash of style, art, literature, and culture.

Yacht Charter Day 1: Lavrio to Kea (Sandy Beaches)

Setting off from Lavrio in the Attica peninsula, which gives us the opportunity to visit classical Athens earlier (from Athens airport), a relatively short sail to green foliage-covered Kea. The closest Cyclades island to Athens, despite attracting a lot of days trippers, Kea features many opportunities for a quiet, quality time, such as the secluded Orkos Beach or fine dining at the “To Spiti Sti Hora” traditional restaurant in Ioulida, on a cliff slope with panoramic views and often featuring live jazz music. The Medieval castle is well worth a visit in the island’s capital, Ioulida, along with the archaeological museum. Speaking of monuments, approximately two miles off the coast of Kea lies the wreck of the “Britannic”, the sister ship of the Titanic, which was discovered by Jacques-Yves Cousteau at a depth of 120 meters, one of the most famous shipwrecks in the world but sadly inaccessible to recreational divers.

Important information:

The seaside village of Vourkari has a quite crowded wharf, so an early dock for your yacht charter is a good idea.

Yacht Charter Day 2: Kea to Antiparos

This is the longest sailing day for your yacht charter, approximately 50 miles, so prepare to spend a full 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 un-spoilt 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).

Yacht Charter 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.

Yacht Charter Day 4: Folegandros to Kimolos

Another short haul back towards the common luxury yacht charter in the Greece area of Milos, and onto sister island 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.

Yacht Charter 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.

Yacht Charter 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.

Yacht Charter Day 7: Serifos to Kythnos

Kythnos is one of the hidden gems of the Greece 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.

Yacht Charter Day 8: Kythnos to Athens (Lavrio)

On to 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, it is a multitude of secluded beaches and bays for you to enjoy.