Milos: Private Sailing to Kleftiko & Caves with Wine & Swim

Private yacht cruise along Milos south coast with cave swims

You’ll sail Milos’ south coast on a classic yacht with a small group, stopping for swims at wild beaches like Kleftiko and exploring sea caves by tender boat. Enjoy chilled local wine, fruit and cheese platters as you float past volcanic cliffs, plus plenty of time to relax or chat with your friendly crew. Expect sun-warmed decks, salty air, and moments that linger long after you’re back on shore.

Step-by-step itinerary

Stops and time spent at each

1. Firiplaka Beachpassing by
2. Kleftiko Beach1h 30m

Private sailing and swimming tour

• Board Veronica classic yacht
• Sail along south coast of Milos
• Stop at Gerakas for swim
• Pass by Tsigrado beach
• Pass by Firiplaka beach
• Pass by Gerontas beach
• Stop at Kleftiko for swim and cave exploration

The experience

I’ll never forget the first moment we left the little port in Milos: one minute it’s the clatter of ropes and sleepy dock sounds, then suddenly you’re out on this old-school yacht called Veronica, just gliding. I thought I’d be nervous (I’m not exactly a sailor), but the crew was so relaxed. The captain, Nikos, handed us cold white wine before we’d even passed Gerakas, where the rocks look like someone sculpted them just for fun. The air smelled salty and sharp, but there was something sweet too, maybe from that fruit platter they set out. I kept touching the rail just to feel how cool it was against my palm.

We stopped at Tsigrado first, or at least drifted close enough to see people scrambling down those wild cliffs with ropes. Our guide laughed and said he used to do it as a kid, “but now I have a boat,” he winked. We could’ve swum there or at Firiplaka (which honestly looked unreal with all those colored rocks), but everyone agreed we wanted more time at Kleftiko. I didn’t expect how quiet it would get when we finally anchored there. Just water slapping the hull and this echo from inside the caves. You can swim through these arches where pirates supposedly hid out. I tried diving under one but mostly just floated, staring up at volcanic shapes that don’t look real in photos.

The best part? We all piled into this little tender boat for cave exploring. It smelled faintly of engine oil and wet stone, which sounds weird but felt right somehow. At one point Nikos pointed out sea urchins clinging to the rocks, “Don’t touch!” he grinned, and then let us jump off for another swim before heading back for more breadsticks and fruit. There’s a shower on board (which is good because salt gets everywhere), plus music if you want it, though honestly most of us just listened to the wind on the way back.

I still think about that light bouncing off white cliffs at Kleftiko, and how time felt slower out there than anywhere else on Milos. If you’re after something private but not stiff or fancy (just real people, good snacks, swimming in places you can’t reach by land), this half-day sailing trip is probably what you want. I wish we’d stayed longer.

What’s included

• Your day includes pickup service in Milos before boarding Veronica classic yacht with your local crew.
• enjoy a cheese plateau with fresh fruits and breadsticks.
• unlimited bottled water.
• chilled white wine plus soft drinks.
• cave exploration using a small tender boat.
• onboard WC and shower facilities.
• high-quality sound system if you want music while cruising back along those volcanic cliffs toward port.

Before you book

Days and timesEvery dayDepartures at 08:30 and 14:00Last departure this season: 30 Nov

Book up to1h before

GroupPrivate

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated 12 days ago

Good to know

Moderate physical effortInfants must sit on laps

Operated by Milos VIP Services

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

How long is the private sailing trip to Kleftiko?

The tour is a half-day experience including several stops along Milos’ south coast.

Is lunch included on the Milos sailing tour?

A cheese platter with fruits and breadsticks is served onboard along with bottled wine and soft drinks.

Can we swim at different beaches during the trip?

Yes, you can stop for swims at places like Gerakas, Tsigrado or Firiplaka depending on your preference before reaching Kleftiko.

Are cave explorations part of this sailing tour?

Yes, cave exploration at Kleftiko is included using a smaller tender boat from your yacht.

Is pickup included for this Milos sailing experience?

The tour includes pickup service as part of your booking.

Is there a bathroom or shower onboard?

Yes, both WC and shower facilities are available on board Veronica yacht.

What drinks are provided during the cruise?

Bottled chilled white wine, Coca-Cola, Fanta, carbonated lemonade and unlimited bottled water are included.

Is this sailing trip suitable for families with infants?

Infants are welcome but must sit on an adult’s lap during the cruise.