11 Milos Sailing Trips Worth Booking

1.Milos & Polyaigos Full-Day Sailboat Tour with Lunch

★★★★★★★★★★4.9 · 1,646 reviews · 10 hours · from $147Our pick

Spend 10 hours with Sailing Milos circling the island and visiting Polyaigos, Gerakas, and Kleftiko. Guides such as Dora, Niki, and Alexandra share local stories while the crew serves snacks, tuna pasta, salad, drinks, and wine. Expect three swim stops, caves, and a motor-powered boat rather than a quiet sailing trip.

“We can’t say enough wonderful things about Katherine and the rest of the crew. Everything was super well organized and the we learned so much about the history and geography of the island. They kept us well fed and the swimming stops were gorgeous. It is a long day though so just keep that in mind if you plan on bringing any kids/older guests as it is a full 10 hour sailing trip.”

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2.Kleftiko Sailing Day Trip with Snorkeling and Lunch

★★★★★★★★★★4.8 · 713 reviews · 8 hours · from $170

Spend eight hours sailing west from Adamas with an experienced crew, stopping at Kalogries, Kleftiko, and Agios Dimitrios. You will snorkel through sea caves, ride a small RIB into narrow rock passages, enjoy Greek food and drinks, and hear island stories from guides such as Giannis, Christos, and Dionysis.

“We took a yacht and sailed to multiple beaches areas around Milos that are only accessible by boat. We snorkeled and swam. Breakfast, lunch, and beverages were provided. Captain Giannis was so amazing. He was so passionate about sailing and sharing the beauty and soul of Greece through his stories and music. Christos and Dionysus were also so kind and shared their knowledge of sailing. An unforgettable, life changing way to experience Milos.”

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3.Best of Milos and Poliegos Catamaran snorkelling Cruise with BBQ

★★★★★★★★★★5.0 · 460 reviews · 9 hours (approx.) · from $241Top rated

Spend about nine hours aboard Polco Sailing’s Lagoon 440, cruising from Adamantas to Poliegos, Kleftiko, Gerakas, and other boat-access-only spots. Expect snorkelling gear, paddleboards, Greek meals, an open bar, Wi-Fi, and photos from the crew. Captains and crew may include Yannis, Dina, Flo, and Andreas.

“Tour was on Sept. 9, 2024. What an amazing tour! The staff members were fantastic, very friendly and chatty. The food was delicious and exceeded expectations. It really was freshly prepared on the catamaran. One of the best things was that this wasn't a "drink your face off" party boat. There was music playing but it wasn't loud at all. It really was a relaxed and enjoyable experience. Highly recommend.”

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4.Half-Day Morning Catamaran Cruise to Kleftiko

★★★★★★★★★★4.8 · 362 reviews · 6 hours · from $182

Join Milos Adventures for a six-hour catamaran cruise from Adamas to Kalogries and Kleftiko. You’ll pass colorful sirmata villages, swim in clear water, explore sea caves, and eat a fresh Greek lunch prepared onboard. Captain George and other rotating crew members keep the day relaxed and well organized.

“We had a lovely and relaxing day on the catamaran and swimming in amazing spots around Milos. The lunch was delicious and crew members very friendly and hospitable! A great way to see Milos”

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5.Catamaran Full-Day of Milos and Poliegos With Lunch & BBQ

★★★★★★★★★★5.0 · 262 reviews · 10 hours (approx.) · from $217

Spend about 10 hours sailing from Adamas around Milos and Poliegos, with swim stops at Kalogries, Kleftiko, Gerakas, and Galazia Nera. Breakfast, fresh BBQ lunch, drinks, snorkeling gear, towels, and an action camera are included. Crew members such as Clara, Elena, Christos, Anastasia, and Despina are praised for warm service.

“It was an unforgettable experience! Clara, Elena and Christos were so wonderful to have on board! The scenic views and swimming spots were amazing”

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6.CATAMARAN Kleftiko Poliegos & Round of Milos Lunch with Openbar

★★★★★★★★★★5.0 · 242 reviews · 9 hours (approx.) · from $289

Spend about nine hours aboard an Odysseus catamaran from Adamantas, circling Milos and Poliegos with swim stops at Kleftiko, Gerakas, Kalogries, and possibly Sarakiniko. The crew prepares breakfast, lunch, snacks, and drinks onboard, while guides such as Silvan, JP, Fay, Christos, and Facundo share stories along the way.

“Amazing way to see Milos! We only had 3 days in Milos and this was an incredible way to see the Island, especially parts of Milos we could only see via boat. The crew (especially Faye) were super friendly and made it so much more fun. The food was delicious, drinks were cold and plentiful, and the views were unreal. Highly recommend!!”

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7.Full-Day Sailboat Cruise with Food and Open Bar

★★★★★★★★★★4.8 · 233 reviews · 9 hours · from $212

Join Captain George, Minoas, and crew from Adamantas for a nine-hour sail around Milos. Swim at Kleftiko, Gerakas, and Blue Bay, see Klima and Skinopi from the water, and enjoy breakfast, lunch, fruit, beer, wine, and snorkel gear. The route changes with wind and sea conditions.

“We had an amazing boat day yesterday! The whole team was truly special, especially Sam from Australia, who made the experience even more fun. The food was excellent, and we always felt safe and well taken care of. The boat took us straight to the best spots around the island, and seeing them directly from the water was unforgettable. I can only recommend this trip – I would choose this boat again any time!”

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8.Kleftiko Sunset Catamaran Cruise with Meal & Drinks

★★★★★★★★★★4.9 · 121 reviews · 5.5 - 7 hours · from $182

Sail from Adamantas on a modern catamaran to Klima, Cape Vani, Sykia Cave, and Kleftiko. You get swimming, snorkeling, SUP, Mediterranean food, an open bar, shaded lounges, and a sunset return. The group is capped at 20, with optional pickup and private bookings available.

“This was a fun afternoon however the sea did not completely play ball with strong winds and a good wind chop. Kleftiko bay was beautiful and we enjoyed a swim here followed by a fabulous dinner. A very enjoyable trip and would highly recommend.”

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9.Full-Day Catamaran Cruise with Food and Open Bar

★★★★★★★★★★4.8 · 102 reviews · 10 hours · from $281

Spend 10 hours aboard the catamaran Together with Odysseus A. Cruises, sailing from Adamantas around Milos and Poliegos. Swim at Kleftiko, Gerakas, Kalogries, and the Blue Lagoon, with fresh meals, an open bar, snorkeling gear, and commentary from the crew.

“The weather was perfect The food was amazing It was worth the extra money for the top of the range experience Our gorgeous three crew members were dedicated to their jobs and good boaties Would definitely recommend to anyone 😀”

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10.Full Day Luxury Catamaran with Full Meal & Open Bar

★★★★★★★★★★5.0 · 91 reviews · 9 - 10.5 hours · from $253

Sail from Adamantas aboard a spacious catamaran for 9 to 10.5 hours. You’ll visit Kleftiko, Polyegos, Triades Beach, Sykia Cave, and Klima, with Greek meals, drinks, SUPs, snorkeling gear, and attentive English-speaking crew. Some departures feature Zacharias and Jozef.

“It was a perfect and truly satisfying experience! Thanks to all the spots and preparations chosen by our guide, I was able to create so many wonderful memories. Highly recommended! The guide and captain were incredibly kind, and most of the guests were from America and Canada. I was able to build such meaningful connections with everyone. It honestly felt like a dream come true. Thank you so much!”

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11.Kleftiko Sailing Cruise with Meal and Swim Stops

★★★★★★★★★★5.0 · 11 reviews · 7 hours · from $212

Join skipper Ilias and the Oneiro crew for a seven-hour sail from Adamantas along Milos’s west coast. You’ll see colorful syrmata houses, swim at Sykia, Kleftiko, and Kalogries, and enjoy Greek food, homemade wine, ouzo, octopus, fruit, and folklore music.

“They were very informative about Milos. They made us feel like we were family. We went on another boat tour two days before this one. All tho it was almost the same tour and we loved that one as well. Adamantas was made it even more special. We plan to come back to Milo’s in a year or two and will be booking with them again.”

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