Private Sailing Charters in Milos: Our Top 11

1.Half-Day Private Romantic Sailing Getaway to Kleftiko

★★★★★★★★★★5.0 · 81 reviews · 5 hours (approx.) Our pick

Review of Milos’ private sailing trip to Kleftiko, with cave access, swimming stops, wine, snacks, pricing, tips, and practical advice.

“Great experience. Both crew members were super nice and knowledgable about what we were seeing across the south coast of Milos. You stop at Kleftiko and go around the caves on the sailship's dingy boat. Then you take some time to swim (they have snorkel goggles) and eat some snacks. After that you go back and stop again on another beach. All the time white wine is available and you can either out your own music. Perfect tour, super recommended.”

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2.Private Daily Sailing Cruise to Discover the Highlights of Milos

★★★★★★★★★★5.0 · 33 reviews · 8 hours (approx.)

Review of Milos private sailing cruise to Sikia, Kleftiko, Klima, and Kalogries, with lunch, drinks, snorkeling, and practical booking tips.

“Excellent experience, highly recommend. The captain was an exceptional person very friendly and helpful.”

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3.Private Catamaran Half Day Afternoon Cruise with Sunset: Kleftiko

★★★★★★★★★★5.0 · 28 reviews · 5 hours 30 minutes (approx.) · from $1,555

Review of Milos’ private Kleftiko sunset catamaran cruise, with sea caves, swimming, Greek food, pricing, timing, and booking advice.

“The tour was absolutely amazing! Captain Polichronis is very humor, making this sailing so much fun. We had unlimited drinks onboard and also very traditional Greek food which were prepared onboard. Luxurious boat and moved steady! Beautiful and clear blue water make you wonder life is beautiful!”

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4.Kleftiko Semi Private Sailing Cruise with Lunch

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

Sail from Adamas to Kleftiko, Sykia, and Kalogries on a seven-hour Milos cruise with swimming, snorkeling, lunch, and drinks.

“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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5.Full Day Sailboat Private Kleftiko & Blue Lagoon with Lunch

★★★★★★★★★★5.0 · 18 reviews · 9 hours (approx.)

Review of Milos private sailing tour to Kleftiko, Blue Lagoon, Sykia, and secluded swim stops, with lunch, snorkeling, and practical tips.

“We had a private tour of the beautiful hidden wonders of Milos. Our captains and guides, Kristos and George were amazing. They made the trip very fun, they were extremely informative and accommodating, they showed us so many places we would not have otherwise k own about and the food was amazing. We highly recommend this to anyone. We didn’t want it to end.”

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6.Private Yacht Tour—Kleftiko Sarakiniko Poliegos

★★★★★★★★★★5.0 · 15 reviews · 5 to 8 hours (approx.) · from $1,021

Review of Milos private yacht tour to Kleftiko, Sarakiniko, Poliegos, and Gerakas, with food, water sports, costs, and booking advice.

“Our private boat tour of Milos was absolutely stunning! We went around the entire island on a half-day tour, and the views were simply breathtaking. The weather couldn’t have been more perfect—sunny skies and no wind made the experience even more magical. A fantastic way to see Milos from the water and an unforgettable highlight of our trip. Highly recommended!”

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7.Full day private sailing cruise around Milos island

★★★★★★★★★★5.0 · 9 reviews

Review of Milos private sailing cruise aboard La Pomme Bleue, with Kleftiko, Sykia cave, local meals, swimming stops, and practical tips.

“Thanks son much Nico and Marion we had the best experience with you both”

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8.2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos

★★★★★★★★★★5.0 · 9 reviews · 2 days (approx.)

Review of a private two-day sailing trip from Milos to Kimolos and Polyaigos, with swimming, Kleftiko caves, meals, and practical tips.

“This was our favorite part of visiting Greece. Sailing is a great way to see the islands. Loved the crew and the destinations”

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9.Milos Private Full Day Catamaran Cruise with Lunch and Drinks

★★★★★★★★★★5.0 · 7 reviews · 9 hours (approx.)

Review of Milos’ private 9-hour catamaran cruise, with Kleftiko, Polyaigos, lunch, drinks, water sports, pricing, and practical tips.

“The crew were so friendly!! We got to enjoy many areas using water sports such as paddle boards, floats, snorkeling gear, noodles. All crew were very accommodating. The main meal was prepared and cooked for us! Light snacks were delicious too. Keep in mind wind may cause rough water. End point location of trip can change, however, a shuttle was provide for us to return on land back to start point.”

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10.Round of Milos & Polyaigos Semi Private Sailing Tour

★★★★★★★★★★4.6 · 4 reviews · 9.5 hours · from $153

Sail around Milos and Polyaigos for 9.5 hours, with swims at Kleftiko, Gerakas, Sarakiniko, lunch, snorkeling, and turquoise bays.

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11.Milos Private Half-Day Catamaran Cruise to Kleftiko with Lunch

★★★★★★★★★★5.0 · 4 reviews · 5 hours 30 minutes (approx.)

Review of Milos’ private catamaran cruise to Kleftiko, with swimming, snorkeling, SUP boards, seafood lunch, drinks, and sunset options.

“Fantastic way to experience the best views of the island. The crew go out their way to make the day special. The food and drinks were all perfect. Highly recommended”

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