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. 

Itineraries provided are intended as examples only. Actual routes may vary based on local conditions, seasonal factors, distances between destinations, and weather considerations at the time of your charter. We encourage you to discuss your route preferences with us. Our experienced team is here to help tailor your plans and provide guidance every step of the way.

Related FAQs

Are the Cyclades Islands suitable for beginner sailors?

The Cyclades are renowned for their beauty and variety, but they’re also known for the Meltemi winds—strong northerlies that blow most consistently from late June to September. Continue Reading...

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

While a 7-day charter is the standard minimum and allows for a rewarding sailing experience, to truly immerse yourself in the diverse beauty of the Cyclades, a 2-week itinerary is highly recommended. Continue Reading...

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

The Cyclades offer a rich variety of islands to explore, from world-famous destinations to hidden gems. Whether you're after lively nightlife, traditional villages, dramatic landscapes, or tranquil anchorages, there's an itinerary to suit your style of sailing holiday. Continue Reading...

What are the bareboat charter base locations for the Cyclades ?

The Cyclades are well served by several convenient charter bases, both on the mainland and within the island group itself. Continue Reading...

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

The prime sailing season in the Cyclades runs from late April or May through to October or early November. Each part of the season offers its own appeal depending on what kind of experience you're after. Continue Reading...

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

The Cyclades enjoy a classic Mediterranean climate, characterised by hot, dry summers and mild, wetter winters. During the sailing season, particularly from late May through September, daytime temperatures typically range between 25–32°C, with long hours of sunshine Continue Reading...

Why sail the Cyclades on a bareboat charter?

The Cyclades, scattered like gems across the Aegean Sea, offer one of the most iconic sailing experiences in the Mediterranean. Known for their whitewashed villages, blue-domed churches, and sun-drenched beaches, these islands are rich in history, character, and natural beauty. Continue Reading...