10 Milos Sailing Tours, Best Day First

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

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

Spend a full day circling Milos and visiting Polyaigos, with swim stops at remote bays, snorkeling at Kleftiko, and lunch served aboard. Guides such as Dora, Nikki, and Alexandra share island stories and keep the mood lively. Three boats carry up to 25 people each. The route can change with the weather.

“Nikki was an amazing tour guide! Mariana who worked onboard as well and helped with our food and drinks was also such a gem. We had a great time and saw the most amazing spots of Milos. Kleftiko was definitely the highlight of our day, it felt like a dream swimming in the most crystal clear waters of Milos. Highly recommend this if you are in Milos, the only way you can see all the beaches that are only accessible by boat.”

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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 aboard a spacious yacht with a small group of up to 26 people. Swim at Kalogries and Agios Dimitrios, explore Kleftiko by snorkel gear and RIB, and enjoy Greek food, drinks, and underwater photos from the crew. Guides speak English, Greek, and Italian.

“The crew were amazing! So positive and happy! The food was excellent! Swimming and snorkeling were so much fun. We had to take a different route due to weather so I was disappointed we did not get to see caves.”

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3.Milos Sailing Tour with snorkeling and lunch

★★★★★★★★★★5.0 · 270 reviews · 8 hours (approx.) · from $181Top rated

Spend about eight hours sailing around Milos from Pollonia or Adamas, with stops at Kleftiko, Sykia, Fyrligos, or Gerakas. You’ll swim, snorkel, explore caves by small boat, and eat a Greek lunch with drinks included. Crew members may include Juliano, Vitaly, RJ, Effi, Christo, or Vasili, depending on the departure.

“This was a really lovely way to spend the day. The tour provided round trip transportation from Pollonia, which was really nice. We were out on the water for about 9 hours and made 3 stops to swim and snorkel. There were about 20 people on our tour. The lunch was delicious and there were beers, soda, and waters available. The travel time felt a little long, but otherwise, the day was well paced with plenty of time for swimming and spending time on the water. There weren’t enough snorkels for everyone on board, which was unfortunate since this was marketed as a snorkel tour. The boat also felt pretty…”

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4.Round of Milos and Poliegos Sailing boat snorkelling cruise

★★★★★★★★★★5.0 · 262 reviews · 9 hours (approx.) · from $193

Spend about nine hours aboard a small sailing boat with a crew such as Andreas, Spyros, or Stavros. You’ll stop at Kleftiko, Kalogries, Gerakas, Poliegos, and other coastal sights for swimming and snorkeling. Lunch, drinks, gear, WiFi, and free GoPro photos are included, but bring a towel and expect a long day at sea.

“The crew were super welcoming, knowledgeable and fun, they made an effort to know everyone on the boat and ensure that we all had a great experience, I'd highly recommend. We went to some beautiful spots and ate delicious food as well as getting the chance to snorkel and I had a wee go on the paddle board”

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5.Adamantas: Milos Sightseeing Sailboat Cruise

★★★★★★★★★★4.9 · 257 reviews · 8 hours · from $223

Spend eight hours sailing west from Adamantas with a maximum of 10 passengers. You’ll visit Cape Vani, Kalogries, Sykia Cave, Kleftiko, and Saint Dimitrios, using a dinghy to reach caves and coves. Crew members such as George, Flora, Forrest, and Pasxalis are known for warm service, good food, and flexible handling of windy days.

“It was amazing! Forrest and Yanis were incredible guides, we truly had an amazing time with them. So much fun!!! Can't recommend this enough.”

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

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

Spend nine hours sailing from Adamantas around Milos, with stops at Kalogries, Kleftiko, Gerakas, Blue Bay, and Poliegos. You’ll swim, snorkel, eat breakfast and lunch, and enjoy beer, wine, soft drinks, and fruit. Captain George and crew members such as Minoas often lead the day, though routes and crew can change with weather.

“It was one of the best days of our trip! Minoas, George and Sam were fantastic!!! Highly recommend!”

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7.Sailing Boat Small Group Kleftiko and Sikia Cave West of Milos

★★★★★★★★★★5.0 · 200 reviews · 9 hours (approx.) · from $169

Set out from Adamas at 8:45 a.m. for a full day along west Milos. Your crew, which may include hosts such as Fay, Christos, Alex, or Tasos, serves breakfast, onboard lunch, drinks, fruit, and snorkeling gear. Expect striking coastal views, several swims, and a small group of up to 18 people, though sails may not be raised.

“My friends and I had such a great time on board the boat, couldn’t fault anything about the experience. The crew were great - super friendly and always there to help. It made our Milos trip amazing, really recommend!!!”

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8.Full-Day Kleftiko Poliegos Sailboat Tour with Lunch

★★★★★★★★★★4.8 · 111 reviews · 9 hours · from $159

Spend nine hours sailing from Adamas along Milos’s volcanic coast, with swim stops at Kleftiko, Gerakas, Agathia, and Poliegos. Christos, George, and the crew serve breakfast, Greek lunch, fruit, beer, wine, and soft drinks. The route changes with the wind, and Sykia Cave is viewed from the boat rather than entered.

“Kristos and George were great fun. Kristos cooked an amazing feed for all of us at lunch and drinks were served at great times never had to wait. Honestly the best day me and my wife could have asked for. Great cruise with 2 amazing hosts would do again if I’m ever in Milos 100%”

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9.Kleftiko Semi Private Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 21 reviews · 7 hours · from $141Best value

Spend seven hours sailing from Adamas along Milos’s colorful fishing villages and volcanic west coast. The route includes Kalogries, Kleftiko, Sykia cave, and Agios Dimitrios, with swimming, snorkeling, drinks, breakfast, a light meal, fruit, and sweets. Lena, Nicolas, Nikos, or Dimitri may be among the crew, depending on the sailing.

“A nice sail to the caves and back. The water was perfect for swimming. The food was decent, if not served a little awkwardly, with bowls placed in a central spot for people to serve themselves.”

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10.Adamantas: Kleftiko Sailing Cruise with Meal and Swim Stops

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

Spend seven hours aboard Oneiro with captain Ilias and a tiny group of up to four. From Adamantas, you pass Milos fishing villages, swim at Sykia, explore Kleftiko’s caves, and stop at Kalogries. Breakfast, lunch, fruit, Greek snacks, drinks, snorkeling gear, towels, and local stories are included.

“Absolutely amazing. I recommend to everyone. Food was delicious, Ilias our captain had so much information to share about his island and so much passion. Was the highlight of our entire Greece trip so far.”

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