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

★★★★★★★★★★ 4.93 (83 reviews) 96% rated it 5 stars

Free cancellationTravelers' pickLikely to sell out

1/26

Duration5h

GroupPrivate

LanguagesEN

Mobile ticketAccepted

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

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.

Good to know

Moderate physical levelInfants must sit on laps

Operated by Milos VIP Services