Milos: Small Group Sailing to Kleftiko & Sikia Cave Lunch

Summary

Sail Milos’ wild coast swim Kleftiko caves eat onboard lunch hear pirate tales

You’ll sail along Milos’ rugged coast with a small group, stopping to swim in clear coves and explore Kleftiko’s pirate caves with your local guide sharing stories. Lunch is cooked fresh onboard at anchor—expect grilled fish and plenty of wine—plus use of snorkeling gear and time to relax on deck as you drift between beaches.

What’s the experience like?

I’ll admit, I was a little nervous when the boat first pulled away from Milos — not because of the sea (it was calm, just a salty breeze), but because I’d never done a small group sailing trip before. There were only about ten of us, plus our captain, Yannis, who had this sun-bleached hair and the kind of smile that makes you trust him instantly. The engine hummed low as we passed Firopotamos Beach — those fishermen’s houses with bright doors right on the water. Someone pointed out how each one’s painted different so the owners could spot them from the sea. It made me think about how practical beauty can be.

The first swim stop was at this quiet cove where the water was so clear you could see every pebble on the bottom. I hesitated before jumping in — it wasn’t exactly warm — but then Yannis handed me a mask and said, “You’ll regret it if you don’t.” He was right. There’s something about floating there, hearing nothing but your own splash and a bit of laughter from the others. We drifted past Cape Vani’s wild cliffs, all rust-red and streaked with yellow and green. The guide started telling us about pirates — apparently Fourkovouni Hill got its name because they used to hang pirates there. That stuck with me for some reason.

Kleftiko itself really does look like somewhere pirates would hide out. White rock arches, caves you can swim through if you’re brave enough (I tried one — scraped my knee, worth it). The crew grilled lunch right on board while we dried off in the sun; fresh fish, tomato salad, bread that tasted like it came straight from someone’s kitchen. There was cold beer too, which hit different after swimming all morning. At one point I tried to say thank you in Greek and pretty much butchered it — Yannis just laughed and poured me more wine.

We stopped at Agios Dimitrios Beach last. Someone swam out to ring the chapel bell (I watched from the deck — next time maybe). On the way back I lay on my towel listening to the boat creak and feeling that salt-sticky skin you get after a day at sea. Even now when I close my eyes I still see those colors under the water at Kleftiko. If you’re looking for a day trip from Milos that feels both easygoing and kind of epic… well, this is it.

Step-by-step itinerary

Day 1 — Explore Milos coastal landmarks and beaches

• Pass by Firopotamos fishing village
• See colorful fishermen houses at Milos Bay
• Visit Fourkovouni hill and hear pirate stories
• View multicolored rocks at Cape Vani
• Relax and swim at remote beach
• Enjoy scenic viewpoint
• Explore Kleftiko pirate shelter
• Swim at Agios Dimitrios Beach and ring chapel bell

Top questions

How long is the sailing tour from Milos to Kleftiko?

The tour covers several stops along Milos’ west coast over a full day trip.

Is lunch included during the sailing trip?

Yes, lunch is cooked onboard at Kleftiko Spot and includes fresh local dishes.

Are drinks provided on this tour?

Beer, wine, bottled water, Coca-Cola, and soda-water are included throughout the day.

Can I snorkel during this day trip?

Yes, use of snorkeling equipment is included so you can swim at multiple stops.

What are some highlights of this sailing tour?

You’ll visit Kleftiko Beach caves, Firopotamos Beach fishing village, Cape Vani cliffs, and Agios Dimitrios Beach chapel.

Is pickup included for this Milos sailing tour?

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

Is this tour suitable for all fitness levels?

Yes, it’s suitable for all physical fitness levels according to the organizers.

What’s included

Your day includes sailing along Milos’ coast with stops for swimming and snorkeling at beaches like Firopotamos and Kleftiko; beer, wine, bottled water plus soft drinks; an afternoon snack of seasonal fruit; lunch cooked fresh onboard while anchored near Kleftiko; local snacks after your first swim; use of snorkeling gear; time to relax on deck before returning in the evening.