Epic 10-day Greek Islands sailing adventure

 

Here’s a suggested epic 10-day Greek Islands sailing adventure that blends iconic spots, hidden gems, ancient ruins, and turquoise waters. This route is ideal for a chartered yacht or sailboat, starting from Athens: -

Day 1: Athens → Kea (1-2 hrs sail)

Kick off with a short sail to Kea, a laid-back island with charming villages. Walk to the Lion of Kea or dine harborside in Korissia.

Day 2: Kea → Kythnos (1.5 hrs)

Sail to Kythnos for hot springs and quiet beaches. Anchor in Kolona Bay — a double beach strip with water on both sides. Magical sunset spot.

Day 3: Kythnos → Serifos (3 hrs)

Cruise to Serifos, an island with wild landscapes and a postcard-perfect hilltop Chora. Great beaches: Livadi for vibes, Vagia for chill.

Day 4: Serifos → Sifnos (1.5 hrs)

Foodie heaven! Sifnos is full of authentic tavernas, pretty villages like Apollonia and Kastro, and epic hiking paths. Don't miss the Church of the Seven Martyrs.

Day 5: Sifnos → Milos (2-3 hrs)

Get ready for Milos, a volcanic marvel with surreal rock formations and over 70 beaches. Explore the lunar landscape of Sarakiniko and pirate coves like Kleftiko.

Day 6: Milos (explore more)

Rent scooters or a 4x4 to check out the island’s interior, catacombs, and old fishing villages like Klima.

Day 7: Milos → Folegandros (2 hrs)

One of the Cyclades’ best-kept secrets. Folegandros has dramatic cliffs, a clifftop Chora, and a serene vibe. Hike up to the Church of Panagia for sunset.

Day 8: Folegandros → Ios (2 hrs)

A mix of party and peace. Chill at Manganari Beach or enjoy the vibrant nightlife. The old town is gorgeous, with whitewashed stairs and views.

Day 9: Ios → Santorini (2-3 hrs)

End with a bang. Sail into the caldera of Santorini — one of the most stunning approaches by sea. Dock in Ammoudi or Vlychada. Explore Oia, Fira, and do a sunset catamaran tour around the volcano.

Day 10: Santorini → Athens (optional ferry/flight return)

Wrap it up with a flight or fast ferry back to Athens — or extend your adventure from Santorini!

Tips: -

Best time: May to October (June and September are sweet spots).

If you’re skippering, check wind patterns (Meltemi winds can hit hard in summer).

Want help booking a route with a skipper or bareboat ?

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