Tour with a sailing boat like a semi private trip with a small group of people. Our local skipper offers a slow close-up approach of the west coast of Milos and gives you a detailed presentation of what you see. He shares with you the historical and geological significance of the island.
Prices change with the date; the lowest is shown.
In demand: 6 of the next 14 departures are already sold out.
From the operator’s live schedule on Viator, checked Oct 6.
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.
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.
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.
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.
Reviews collected by Viator and Tripadvisor
Excurgo comparison of 171 Viator tours, recalculated daily.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Milos oneiro-kleftiko sailing experience with local guide lasts about 7 hours. The itinerary has 4 stops.
Prices start at $159 per person for this Milos experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
According to the operator’s current schedule, it runs every day, starting at 8:40 AM.
It can: 6 of the next 14 departures are already sold out, so booking ahead is a good idea.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
The meeting point is At the port , 50 meters of bus station, next to the moto parking area. Hotel pickup is not part of this experience.
The experience is available in EN.
It is a small-group experience with a maximum of 16 participants.
Yes, bookings are confirmed instantly.
Travellers rate it 5.0 out of 5 across 498 reviews on Viator and Tripadvisor; it is run by Milos Oneiro.
Reviews collected by Viator and Tripadvisor
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.
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.
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.
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!
Just book this one. I think every boat that saw us was jealous because of the amazing meals and experience we were having.
This trip exceeded all of our expectations! The scenery and swimming were beautiful, the captain and crew were friendly, the food and drinks were very good, and the information shared about the history of Milos was really interesting. Thanks for a wonderful day!
Cannot rate this experience high enough! It was truly amazing! Captain Elias showed us amazing spots, had great stories about Greek history and Greek life! The meals and drinks were also fantastic! The personal touch they put into the day shows the entire time you are on the boat!
Prior to the tour we received a notice that the location of the meeting point was changed, but they did provide transportation to and from. Total of 16 ppl on the shop. Met the captain, Elias, along with 2 crew members. Within 15 mins or so, we were given fruit bowls. Then some appetizers of sandwiches and breakfast snacks. Plenty of juices, waters and coffee as well. We toured the south side of the island, stopped at a few spots to snorkel and visit beaches. Stopped for an amazing lunch. Greek salad, pasta with seafood. Plenty of wine and beer were offered to us. Later we had fresh grilled octopus and ouzo. Elias told us of the history of Santorini and the volcano along with detailed explanations about all of our stops. Loved that it was a small crowd of only 16 ppl, which allowed great interactions. The crew definitely was attentive and helpful for the entire cruise. Loved the whole experience.
We had a great day with Captain Elias and his crew and would thoroughly recommend this trip to anyone wanting a sailing trip excursion from a cruise ship because the whole experience was fabulous and the timings worked perfectly. Gusty winds meant that we were not able to join the yacht itself in Port Adamas, but we still met there ( 2-3 mins walk from where the cruise ship tenders landed) and then were driven to our starting point on the south of Milos where we joined about a dozen other passengers. We had a great time, listening to Greek music, sailing, swimming, enjoying the breathtaking scenery and tasting home grown produce, fresh octopus and Elias' brother's wine! We were driven back to Adamas, in plenty of time to get the tender back to our ship. All in all a prefect day! Thank you.
This cruise was one of the highlights of our time in Greece! The knowledgeable captain provided history of the island while we cruised, and we were provided with homemade wine, local beer, fresh grilled octopus and plenty of other food throughout the day. The beaches, views, and snorkeling were great! We really like that it was a smaller group compared to other tours, made it more intimate. The crew were super attentive and this definitely made the experience. Would do it again for sure!
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Milos oneiro-kleftiko sailing experience with local guide | 7 hours | 5.0 (498) | $159 | |
 Sailing Boat Kleftiko and Sikia Cave West of Milos | 9 hours | 4.9 (246) | $138 | View |
 Kleftiko Full Day Sailing Cruise with Snorkeling & Lunch | 9–10 hours | 4.8 (166) | $160 | View |
 Half-Day Private Romantic Sailing Getaway to Kleftiko | 5 hours | 4.9 (85) | $686 | View |
 Milos Kleftiko Sailing Cruise with Lunch, Drinks & Snorkeling | 7 hours | 4.7 (18) | $126 | View |
 CATAMARAN Kleftiko Poliegos & Round of Milos Lunch with Openbar | 9 hours | 5.0 (460) | $216 | View |
 Sailingboat: Kleftiko & Poliegos Full Day with Lunch & Open bar | 10 hours | 4.8 (357) | $155 | View |