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Can you give an example itinerary for the Cyclades less-visited islands

A Cyclades Sailing Itinerary: Hidden Gems from Lavrion

Set sail from Lavrion and experience a side of the Cyclades few tourists see. This one-week itinerary is ideal for those who prefer quiet bays, traditional villages, and authentic Greek island life—whether bareboating or with a hired skipper.

Day 1: Lavrion to Kythnos (Kolona Bay)

Begin your charter with a 3–4 hour sail to Kythnos. Anchor at Kolona Bay, known for its striking sandbar that joins two hills. It's a serene and scenic spot to ease into island life—perfect for a sunset swim and a peaceful first night aboard.

Day 2: Kythnos to Serifos

Sail south for about 4 hours to Serifos and dock at Livadi. Take the steep walk or a taxi up to Chora for panoramic views and a stroll through this unspoiled Cycladic village with timeless charm.

Day 3: Serifos to Sifnos

Enjoy a short, easy sail to Sifnos, an island famed for its whitewashed architecture and culinary heritage. Anchor at Kamares, offering safe mooring and access to Apollonia and the historic hilltop village of Kastro.

Day 4: Sifnos to Kimolos

A 2–3 hour sail brings you to Kimolos, a quiet alternative to nearby Milos. Anchor at Psathi harbour or find a sheltered cove—this island is ideal for swimmers, snorkellers, and anyone seeking tranquility.

Day 5: Kimolos to Polyaigos

Just a short hop to uninhabited Polyaigos, where Blue Bay awaits. This is one of the Aegean’s most beautiful and remote spots. Spend the night under the stars—pure magic.

Day 6: Polyaigos to Kythnos (Loutra)

Cruise north back to Kythnos, this time anchoring at Loutra, a seaside village known for its natural hot springs and laid-back atmosphere.

Day 7: Kythnos to Lavrion

Return to Lavrion with an early start to allow 5–6 hours’ sailing. Time permitting, stop at Makronisos or anchor off the Temple of Poseidon at Cape Sounion for a memorable finish.

Why We Love This Route

This itinerary skips the busy tourist harbours and focuses on smaller, less-developed islands with authentic character. It suits experienced sailors or those hiring a local skipper to help navigate the more open passages.

We’ll tailor this itinerary to your preferences and help select the best yacht for comfort, handling, and your group’s experience level.

See also this FAQ. 

Related FAQs

Are the Cyclades Islands suitable for beginner sailors?

The Cyclades are known for their beauty - and also the Meltemi winds Continue Reading...

How long should a boat charter in the Cyclades typically be?

To truly enjoy the Cyclades, a 2-week itinerary is recommended. Continue Reading...

What are some popular islands and routes to consider when sailing the Cyclades?

The Cyclades offer a rich variety from famous spots to hidden gems Continue Reading...

What are the bareboat charter base locations for the Cyclades ?

The Cyclades are well served by several convenient charter bases Continue Reading...

When is the best time to sail in the Cyclades Islands?

The prime Cyclades sailing season runs from late April to November Continue Reading...

What are the typical weather conditions and winds in the Cyclades?

The Cyclades enjoy a classic Mediterranean climate, Continue Reading...

Why sail the Cyclades on a bareboat charter?

The Cyclades offer an iconic Mediterranean sailing experience Continue Reading...

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