Milos: Kleftiko Sailing Trip & Pirate Stories with Lunch

Summary

Sailing west milos to kleftiko caves with stories food and sea

You’ll sail along Milos’ wild west coast with a small group, hearing pirate legends from your local skipper as you pass colorful fishing villages and swim through Kleftiko’s caves. Enjoy breakfast, fresh Greek lunch with ouzo, snacks, and music on board — plus plenty of time in warm bays and under those impossibly white cliffs.

What’s the experience like?

Ever wondered what it feels like to drift past those wild white cliffs of Milos, just close enough to see the colors in the fisherman’s houses? We left Adamas early — not too early for breakfast though, which was a relief because I can’t function without coffee. Our skipper, Yannis, greeted everyone with this easy grin and started pointing out villages like Klima and Fourkovouni. The houses there are so bright they almost look painted on. He explained how the fishermen used to pull their boats right into their homes — I tried picturing that and honestly, it made me smile. There was a salty breeze and that faint diesel smell you always get near boats.

I didn’t expect Kleftiko to be so quiet. You’d think a place famous for pirate hideouts would feel dramatic but it was just… silent except for the water slapping against the hull. Yannis told us stories about pirates hiding in these caves — he even did voices, which cracked us up. We swam into one of the caves (the water is colder than it looks) and the light inside turned everything this weird blue-green color. Lunch was served right there: tomatoes so ripe they almost burst, grilled octopus that tasted smoky-sweet, and ouzo if you wanted it. I probably ate more than I should have but who cares when you’re staring at those cliffs?

Afterwards we stopped at Kalogries Bay for another swim — shallower water this time, warmer too. Someone put on Greek music (I still have that melody stuck in my head) and people just lounged around or jumped off the side. There was fruit salad at Sykia cave earlier too — I forgot about that until now because I was distracted by trying to say “Sykia” properly (Yannis laughed at my attempt). The trip back felt slower somehow; maybe we were all sun-dazed or just not ready for it to end yet.

Step-by-step itinerary

Day 1 — Sailing tour of Milos west coast

• Depart from Adamas with welcome
• Enjoy breakfast on board
• Pass traditional fishing villages
• Skipper presents village history
• Visit Sykia open-roof cave
• Swim and see sea bottom
• Eat fresh fruit salad
• Arrive at Kleftiko for guided tour
• Hear pirate stories from skipper
• Swim in caves and explore
• Have lunch with sea view
• Sail to Kalogries bay
• See West Milos beaches closely
• Swim in shallow warm water
• Enjoy ouzo and grilled octopus
• Sail past Vani and Klima
• Return to port

Top questions

How long does the Milos sailing tour take?

The total duration includes travel time; expect a full day trip along Milos’ west coast.

Is lunch included on the Kleftiko sailing trip?

Yes, a fresh Greek lunch is served on board during your stop at Kleftiko Beach.

Are swimming stops part of this day trip?

Yes, you’ll have several chances to swim at Kleftiko caves, Sykia area, and Kalogries Bay.

Does this tour include breakfast or snacks?

Breakfast is served after departure from Adamas; snacks like fruit salad are also included during the day.

Is transportation provided to the boat departure point?

No hotel pickup is mentioned; public transportation options are available nearby Adamas port.

What makes this sailing trip different from others?

This semi-private tour features a local skipper sharing pirate stories and close-up views of Milos’ west coast villages and beaches.

Is this sailing tour suitable for everyone?

The tour suits most fitness levels but isn’t recommended for travelers with poor cardiovascular health.

What’s included

Your day includes breakfast after boarding in Adamas port, guided narration by a local skipper as you pass traditional fishing villages along Milos’ west coast, swimming stops at Kleftiko Beach caves and Kalogries Bay, fresh Greek lunch with ouzo on board plus snacks like fruit salad — all shared with a small group before returning by boat in the afternoon.