2-Day Private Sailing Tour: Milos, Kimolos & Kleftiko Beach

Sleep on a sailboat anchored off Milos, then wake to Kleftiko's sea caves and Polyaigos's uninhabited bays.

A 2-day private sailing tour around Milos, Kimolos and Polyaigos on a 13-meter boat with one night aboard. You swim at Kleftiko Beach, Sarakiniko and Firopotamos, explore sea caves by dinghy, and sleep either at the port of Psathi or at anchor in a bay. Breakfast, lunch and drinks are included each day. The itinerary adjusts for weather and wind direction.

Step-by-step itinerary

Day 1: Sailing Milos and Kimolos islands

• Sail to Klima village
• Swim at Firopotamos Beach
• Visit Sarakiniko Beach and cliff-jump
• Lunch at Goupa beach in Kimolos
• Arrive at Psathi port for overnight
• Walk to Kimolos village
• Enjoy cocktail and seafood dinner

Day 2: Explore Polyaigos and Milos bays

• Swim and sunbathe at Myrsini bay
• Relax at Firopotamos Beach
• Explore Kleftiko bay and caves
• Have lunch onboard sailboat

The experience

The boat leaves from Adamas and sails first to Klima, a picturesque fishing village, then to Firopotamos Beach on Milos's north shore: a sandy bay with typical Cycladic houses where the water is clear enough for a midday swim. From there you reach Sarakiniko, the "moon landscape beach" with white cliffs that rise straight from the water. Cliff-jumping is possible from the boat. Lunch happens at Goupa Beach in Kimolos, also called "the elephant beach" for its shape, where you swim before and after eating fresh Mediterranean food. The first day ends at the port of Psathi in Kimolos, where you sleep aboard the boat or at free anchor in a nearby bay. The village itself sits 15 minutes' walk uphill and is a genuine Cycladic settlement with restaurants and patisseries along the waterfront.

Day two takes you to Polyaigos, an uninhabited island, starting with a swimming stop at Myrsini Bay. You return to Firopotamos for another swim, then sail to Kleftiko: the most famous bay in the area, named for its history as a pirate hideout. The captain takes you into the sea caves by dinghy or paddle board, and lunch is served aboard. The boat operates with a live guide who speaks English, French or Greek, and the crew adjusts swimming stops and the exact route depending on wind and weather each day.

All boat expenses, fuel, taxes and berth fees are covered in the price. You bring your own snorkel gear if you have it, though the stops are mainly for swimming and exploring rather than reef diving. The overnight stay means you pack light and leave luggage at your hotel in Adamas. The boat has basic sleeping quarters and you wake to the sound of water.

What’s included

• All boat expenses, fuel, taxes and berth fees.
• breakfast and lunch both days.
• drinks throughout.
• one night aboard the sailing boat at Psathi port or at anchor.
• a live guide speaking English, French or Greek.
• pickup from your hotel or Adamas.

Before you book

Days and timesNext departure: 27 May 2027

Book up to12h before

GroupPrivate

Live guideEnglish, French and Greek

Meeting point and pickupHotel pickup is optional; you can also go straight to the meeting point. Ends back at the starting point.You can choose from 4 pickup points.

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?The guide speaks English, French or Greek, so book this tour if you're comfortable following commentary in one of those languages. The 2-day format means you sleep aboard and have a full second day exploring Polyaigos and Kleftiko, unlike the 1-day sailing trips that leave and return the same day.

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Top questions

What languages is the tour guided in?

Live guide in English, French and Greek.

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 can you really explore the caves?

Kleftiko is a bay ringed by tall white cliffs on Milos's west coast, famous as a former pirate hideout. The captain takes you into the sea caves by dinghy or paddle board so you can paddle inside and see the rock formations up close. You don't need diving certification or special gear.

Where do you sleep on the boat, and is it comfortable for two nights?

You sleep aboard the 13-meter sailing boat either moored at the port of Psathi in Kimolos or at free anchor in a bay nearby. The boat has basic sleeping quarters. It's a working vessel, not a hotel, so comfort is simple but functional for one night (the tour is 2 days, with the second day ending back in Adamas or at your next port).

What happens if the weather is bad or the wind is too strong?

The operator reserves the right to modify the itinerary and move swimming stops depending on weather and wind direction each day. The route is flexible so that you still visit the main sites (Kleftiko, Sarakiniko, Polyaigos), but the exact sequence and timing may shift to keep the boat safe and comfortable.

Is lunch really included, or do you have to pay extra?

Breakfast and lunch are included both days, along with drinks. Dinner on the first night is not included, so you can eat at one of the restaurants in Psathi village or aboard if the boat offers it. Gratuities for the crew are separate.

Do you need sailing experience or special fitness to join?

No sailing experience is needed. You're a passenger on a private boat with a professional crew. The tour suits all physical fitness levels. Infants must sit on an adult's lap, and service animals are allowed.

How do you get to the boat, and what time does it leave?

Pickup is included in the tour price. The boat departs from Adamas, the main port of Milos. Your guide will confirm the exact meeting time and location when you book.