Private Sailing Cruise Milos: Kleftiko Beach & Hidden Caves

Sail to four boat-only beaches and swim in caves the road cannot reach

A private eight-hour sailing cruise around Milos takes you to Kleftiko Beach, Sikia's volcanic bay, the village of Klima and Kalogries beach: four stops mostly reachable only by water. The 13-meter sailing boat carries your group with shaded areas on deck. Lunch, snacks, drinks and paddleboards are included. A live guide speaks English or French. Strong north winds may require a change of route to protect access to Sikia.

Step-by-step itinerary

Sailing cruise exploring Milos highlights

• Sail to Sikia beach
• Swim and paddle at Sikia
• Sail to Kleftiko pirate's bay
• Snorkel and paddle-board at Kleftiko
• Have lunch and drinks at Kleftiko
• Sail to Klima village
• Sail to Kalogries beach
• Swim and snorkel at Kalogries

The experience

The boat leaves in the morning and sails first to Sikia beach, where a volcanic bay and sea cave open up to swimmers and paddleboarders. You get appetizers and drinks here, plus time in the water before the crew moves on. Kleftiko comes next: the pirate's bay, ringed with caves you can snorkel around and explore by paddleboard. Lunch and more drinks happen here, so you eat on the water with the cliffs around you.

The afternoon takes you to Klima, a fishing village built into the rock with boat garages carved into the waterfront, then to Kalogries beach, which has no road access at all. Swimming, snorkeling and paddling are the point here. The crew handles the sailing while you decide how long to stay in the water at each stop. Shade on the 13-meter boat means you're not cooking between swims.

The eight-hour day includes all food and drink, so you bring nothing but a towel and sunscreen. If north winds make Sikia unreachable, the crew picks another area instead: the route adapts to conditions, not the other way around.

What’s included

• Lunch and snacks.
• bottled water and alcoholic beverages.
• paddleboards for use at each stop.
• shaded seating on the boat.
• fuel surcharge and parking fees.
• a live guide in English or French.

Before you book

Days and timesNext departure: 27 May 2027

Book up to12h before

GroupPrivate

Live guideEnglish and French

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 yesterday

Good to know

Low physical effortPets welcomePublic transport nearbyInfants must sit on laps

Operated by Oscar Private Sailing

Is this one for you?This is a private boat, so your group sails alone with the crew and has the flexibility to spend more time at whichever stop appeals most. Choose it if you want the boat-only beaches without sharing the space or the schedule with other travelers, or if your group has children and wants to move at their own pace between swims.

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Top questions

What languages is the tour guided in?

Live guide in English and French.

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.

What is Kleftiko Beach like, and what can you do there?

Kleftiko is a bay surrounded by sea caves and accessible only by boat. You can snorkel around the rocks, explore the caves by water, use a paddleboard to paddle deeper into the bay, and swim in the open water. Lunch is served here.

Is the boat shaded, and what happens if the weather turns rough?

The 13-meter sailing boat has shadow areas on deck where you can get out of the sun between stops. If strong north winds arrive, the crew cannot safely reach Sikia beach and will sail to another area instead, keeping the day safe and still full of swimming and snorkeling.

What food and drinks are on the boat?

Lunch, snacks and drinks are included throughout the day. You also get appetizers at Sikia and drinks at Kleftiko. Alcoholic beverages and bottled water are both available.

How many hours is the cruise, and when does it start?

The cruise runs eight hours. The exact start time is confirmed when you book. The crew will tell you the departure point and pickup details at that time.

Can you bring children or infants on this boat?

Yes. Infants must sit on an adult's lap during the cruise. The boat is suitable for all fitness levels, and service animals are allowed on board.