Milos oneiro-kleftiko sailing experience with local guide

Highlights

Inclusions

Itinerary

1. Departure area . We depart from Adamas with a warm welcome and a few words about the bay. The breakfast is served. We pass through the traditional fisherman villages of Skinopi, Klima, Areti and Fourkovouni which will amaze you with their colorful small fisherman houses called syrmata. The skipper offers a slow close-up approach and detailed presentation of their significance and their use.

   Passes by

2. Upon arrival to Kleftiko you are treated with a guided boat tour of the entire area accompanied with a fascinating narration of incredible pirate stories by the skipper. It is possible to swim in or around caves, to experience the adventure, to discover hidden places and to enjoy the nature of Kleftiko. During your stay there you are offered a scrumptious lunch with a view of the imposing white rocks and the crystal turquoise waters.

   2 h

3. After Kleftiko we reach Kalogries bay. On the route you get to see the beaches of West Milos up close : Agios Ioannis, Triades and Ammoudaraki. There we relax for an afternoon swimming in shallow warm water. On the boat is offered ouzo with grilled sun-dried octopus, traditional snacks of Milos accompanied by Greek music. On our way back, we sail off Vani again and with open sails we pass from Klima and arrive in the port.

   1 h

4. The first destination of the day is at Sykia area to admire the open-roof cave. An impressive sea bottom is revealed while swimming in the cave waters. Fresh fruit salad is served.

   45 min

Cancellation

Free cancellation up to 24 hours before the experience starts, for a full refund.

Reviews

Ratings come from 500 reviews collected by our booking partner. They are travellers' own words, in the order they were written — never reordered to flatter the experience.

Showing reviews written in English.

• 5Amazing day

  We loved our sailing day with Oneiro! Due to weather the plan had to be adjusted, but the crew was incredibly communicative, professional and planned an amazing day! They had jackets for everyone at the start when the wind was going, but the boat was still so smooth and our captain was so knowledgable about all the areas and history! We got to go in to a cave, swim around Kleftiko and had amazing food on board! Would 100% book again!

  Y2186SSkimberlysOctober 2026via Tripadvisor

• 5Highly Recommend!

  We had the most incredible boat trip. Because of the bad weather, the captain re-routed us to the south shore so that we could sail a safer route. And still the trip was smooth sailing and we always felt safe and had plenty of swimming opportunities. The team was able to accommodate to our allergies and were so hospitable, providing jackets and towels if we needed them. The food itself was very good, especially the lunch! Would highly recommend this experience, the stories they shared and knowledge of the area made everything so much better.

  meganmC7505UROctober 2026via Tripadvisor

• 5Four seasons in one sailing adventure.

  We had the most amazing day. The weather was not ideal so our trip was changed and we got to see and experience so much more. The crew were delightful, the captain, extremely knowledgeable and the food was delicious. We couldn’t recommend this tour more highly.

  A425SRsusannOctober 2026via Tripadvisor

• 5A masterpiece of Greek hospitality

  Captain Elias and his crew gave us an extraordinary day. We had three swimming stops—almost an hour each—among spectacular cliffs and caves, with no sense of being rushed. Between swims, food appeared with perfect timing: breakfast, an excellent fresh fruit salad, salad and seafood linguine, and finally octopus with ouzo. The homemade white wine was so popular that people kept asking for more. Elias has the gift of a great professor: he knows how to inform, entertain, organize and turn a boatful of strangers into a real company. For the final ouzo, he gathered everyone around an improvised table at the stern, poured the drinks and told stories. By then, we were no longer passengers—we were friends. Everything felt effortless, joyful and authentic: beautifully orchestrated, but never staged. Elias also judged the changing weather perfectly, bringing us back just ahead of the heavy rain. This was far more than a sailing tour. It was living theatre—and one of the finest experiences of our time on Milos.

  Alexander_DSeptember 2026via Viator

• 5This is a MUST do tour with this company.

  From start to finish you do not feel like a tourist- but like family. Between the warmth of the staff, the attentiveness of the captain, and seamless execution of this tour left us in awe. This is not like your normal boat tour, this is an experience you will not forget and surely the best way to experience Kleftiko.

  KristieNYSeptember 2026via Tripadvisor

• 5Spectacular scenery, excellent food & exceptional staff

  Our sailing trip in Milos with Captain Elias and his wonderful crew was the highlight of our trip to the Greek Islands. It was an action packed day, including fantastic food (breakfast, lunch & snacks) and homemade wine (and beer) and visits to the most spectacular caves, beaches and inlets. But the best part of the day was listening to Elias tell us about the island and its history and entertaining us with his great story telling about pirates, mythology and the people who live there. He is a true local who is passionate about the island and the community which was evident from the engaging conversations he had with other local fisherman and residents we encountered on our trip. We cannot recommend this trip highly enough!

  catrionah445September 2026via Tripadvisor

Know before you go

How it compares in Milos

• Its from-price is 33% below the median of the 61 day trips we list in Milos.
• Its length is typical for the group.
• By number of reviews it ranks 3 of 61.
• The operator lists free cancellation on it.

About Milos

Milos is a volcanic Cycladic island of white cliffs, sea caves and fishing hamlets, where the Venus de Milo was found in 1820.

Milos was shaped by volcanoes, and its coast is a patchwork of white, yellow and rust-coloured rock. Plaka, the hilltop capital, is a whitewashed village of winding lanes below a medieval kastro, and Adamas is the main port. A farmer found the Venus de Milo in 1820, and the statue now stands in the Louvre. Obsidian from the island was traded around the Aegean in prehistory.

Top-ranked sights in Milos: Kleftiko Beach, Sarakiniko Beach, Firopotamos Beach.

See all 154 experiences in Milos