Set sail on a private 8-hour cruise around Milos with Oscar Private Sailing. Swim in crystal waters, visit iconic beaches like Kleftiko, and savor fresh Mediterranean dishes on this unforgettable island adventure.
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Difficulty
easy
Duration
8 hours
Fitness Level
Suitable for most fitness levels; requires basic swimming ability and comfort in the water.
Wildlife
History
Milos’s unique volcanic geology has influenced its history, including ancient mining and shipwrecks along its rugged coast.
Conservation
Efforts focus on protecting marine habitats near Kleftiko and maintaining water quality to preserve Milos’s pristine ecosystems.
Oscar Private Sailing
Set sail on a private 8-hour cruise around Milos with Oscar Private Sailing. Swim in crystal waters, visit iconic beaches like Kleftiko, and savor fresh Mediterranean dishes on this unforgettable island adventure.
Oscar Private Sailing is a private sailing operator based in Adamantas, Milos, Greece, offering curated small-group and private yacht experiences around Milos, Kimolos, and Polyaigos. The company organizes a range of trips from single-day 8-hour cruises to multi-day voyages that include overnight stays aboard a sailing yacht.
Trips highlighted by Oscar Private Sailing include short highlights around Milos (including destinations such as Kleftiko and Sikia cave), an 8-hour Kimolos and round of Polyaigos cruise departing from Pollonia, a two-day option with an overnight stay, a three-day (56-hour) three-island itinerary, and a four-day tour that includes a day in Sifnos. Onboard offerings frequently feature homemade Mediterranean cuisine and opportunities to swim in clear waters; some trips provide an underwater GoPro for guest use during swimming stops.
Oscar Private Sailing operates from Adamantas and focuses on delivering personalized sailing itineraries that emphasize coastal exploration, secluded beaches, and relaxed multi-day experiences under the stars. The business is featured on The Adventure Collective, and listings emphasize private charters, local culinary touches, and access to uninhabited or less-visited islands. Communication, clear itineraries, and safety on board are described in trip summaries and booking information. Guests looking for private sailing departures from Adamantas and nearby Milos ports can select from defined 8-hour cruises up to multi-night voyages offered in the trip lineup.
Base Location
Adamantas, Greece
Sailing departures from Adamantas, Milos
Trip Durations
8–56 hours
Day cruises to multi-day voyages
Meals Onboard
Homemade Mediterranean
Fresh local cuisine prepared onboard
Tours Offered
5 distinct trips
Day, overnight, and multi-day options
Choose an 8-hour cruise, a two-day overnight sail, or a multi-day island voyage and secure dates for Oscar Private Sailing.
Book Early for Preferred Dates
Private charters have limited availability—reserve your spot well in advance to secure your preferred day.
Bring Reef-Safe Sunscreen
Protect yourself and the marine environment by using eco-friendly, reef-safe sunscreen when swimming or snorkeling.
Arrive Prepared for Swimming
Wear or bring quick-dry swimwear and water shoes for comfort when entering rocky coves or climbing aboard the dinghy.
Download Photos After Tour
Don’t forget to save the USB stick with underwater and sailing photos provided by the crew to remember your day.
Reef-safe sunscreen
Protects your skin and preserves the fragile marine ecosystem.
summer
Swimsuit and quick-dry towel
Necessary for swimming in crystal-clear Aegean waters and drying off quickly.
summer
Water shoes
Provides grip and protection on rocky shorelines and boat decks.
summer
Light jacket or windbreaker
Keeps you comfortable against sea breeze and shifting weather conditions.
spring|fall