11 Private Sailing Charters in Milos Worth a Whole Day

1.Half-Day Private Romantic Sailing Getaway to Kleftiko

★★★★★★★★★★5.0 · 81 reviews · 5 hours (approx.) · from $784 per boatNumber one

Set out from Agia Kyriaki with a private crew, often including Dimitris, Jim, James, Nicko, or other Milos VIP Services captains. Cruise to Kleftiko, swim at quiet southern beaches, and use the small tender to pass through sea caves. Wine, fruit, cheese, water, music, a shower, and a WC are included.

“My group of 4 friends chose to do this private tour instead of one of the larger group tour options on the island and it was so worth it! We are not experienced enough to rent/drive a boat on our own, and so this was a perfect choice for us. The tour starts at Agia Kiriaki Beach, there is plenty of parking on site, and then you'll meet your tour guides in front of the tavern. Our captains were so friendly, helpful, and ensured we were comfortable the entire time. We loved the snacks and wine provided. They also took pictures of us! The tour itself is great, you get…”

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

★★★★★★★★★★5.0 · 33 reviews · 8 hours (approx.) · from $1,388 per boat

Spend about eight hours aboard a private crewed sailboat from Adamantas, visiting Sikia, Kleftiko, Klima, and landless Kalogries Beach. Captain Nikos, Evangelos, Stathis, and Joanna are among the crew named by guests. Lunch, snacks, drinks, snorkeling, and paddleboards are included.

“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

Set sail from Adamantas at 3:00 pm on a private catamaran for Kleftiko’s caves, swimming, snorkeling, and a fresh Greek meal prepared aboard. Continue to Kalogries Beach before returning around sunset. Crew members may include Captain George, Ilias, or Captain Polichronis, and the skipper can adjust the route for weather.

“We had the most accommodating Captain George and First Mate, Ilias from start to finish. They both took such great care to make sure our trip was everything we hoped it would be. Ilias prepared a delicious feast. Captain George personalized our trip, pointed out trip highlights of this beautiful area, and answered all our questions. This was the highlight of our time in Milos. It couldn’t have been more perfect!”

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4.Kleftiko Semi Private Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 21 reviews · 7 hours · from $141Cheapest deck

Set sail from Adamas with Lena, Nikolas, Dimitri, or Nikos, depending on the departure. You’ll pass colorful fishing villages, swim at Kalogries and Kleftiko, peer into Sykia cave, and enjoy lunch, drinks, fruit, and sweets aboard a semi-private cruise of about seven hours.

“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.) · from $1,141 per boat

Spend about nine hours on a private sailboat from Adamantas, visiting Kleftiko, Sykia Cave, Kalogries, Gerakas, and Poliegos’ Blue Lagoon. The crew, including guides such as Christos, George, Clara, or Nikos depending on the day, serves breakfast snacks and lunch, shares island history, and provides snorkeling gear and noodles.

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6.Private Yacht Tour—Kleftiko Sarakiniko Poliegos

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

Set out from Agia Kiriaki on a private yacht with an English-speaking crew. Visit Kleftiko, Sarakiniko, Poliegos, Gerakas, sea caves, Bear Rocks, and quiet coves. Expect swimming, snorkeling, paddleboarding, local food, wine, and a flexible route shaped by weather. Kosta and Maria have hosted private trips, with sea scooter use available on request.

“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 · from $1,636 per boat

Spend about nine hours sailing Milos with Niko and Marion aboard the 43-foot Oceanis yacht La Pomme Bleue. Swim at Agathia, Agios Ioannis, Kleftiko, and Agios Dimitrios, or enter Sykia cave when conditions allow. Your private group of up to eight gets breakfast, lunch, drinks, snorkeling gear, and a dinghy tour of Kleftiko.

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

★★★★★★★★★★5.0 · 9 reviews · 2 days (approx.) · from $2,937 per boat

Spend two days aboard a private sailboat from Milos with stops at Sarakiniko, Klima, Kimolos, Polyaigos, Gerakas, and Kleftiko. You’ll swim from quiet coves, explore a sea cave by dinghy or paddle board, enjoy breakfast and two lunches, and sleep overnight at Kimolos’ small port. Pickup is limited to two people.

“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.) · from $3,485 per boat

Set out from Adamas at 10 a.m. on a private catamaran for up to 15 people. Swim at Kalogries, explore Kleftiko’s white cliffs, and visit Polyaigos’ clear Galazia Nera Bay. Your crew serves lunch, snacks, beer, wine, soft drinks, and local specialties. Snorkeling gear, SUP boards, fishing gear, and WiFi are included.

“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

Leave Adamas at 09:30 for a full day around Milos and Polyaigos. With guide Leonidas and an experienced captain, you’ll swim at Gerakas, Kleftiko, and Galazia Nera, explore Sykia cave, see fishing villages and sulfur mines, and enjoy breakfast, a light meal, fruit, sweets, drinks, and snorkeling gear aboard.

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

★★★★★★★★★★5.0 · 4 reviews · 5 hours 30 minutes (approx.) · from $2,839 per boat

Sail from Adamantas to Kleftiko on a private catamaran for up to 15 people. Your crew serves coffee, local pies, unlimited soft drinks, beer, and white wine, then prepares a Mediterranean lunch onboard. Stop at Sykia Cave for photos, swim and snorkel at Kleftiko, or choose an afternoon departure for sunset views.

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