Set sail through the Greek Cyclades on a three-day adventure with Oscar Private Sailing. Discover secluded beaches, pristine waters, and timeless island charm—perfect for a memorable maritime escape.
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Difficulty
easy
Duration
56 hours total
Fitness Level
Suitable for most fitness levels; no technical skills required
Wildlife
History
The Milos area has a long volcanic history, with the island of Milos hosting the famous statue of the Aphrodite of Milos (Venus de Milo).
Conservation
The sailing trips emphasize eco-friendly practices, including waste management and respecting marine habitats to preserve the area’s natural beauty.
Oscar Private Sailing
Set sail through the Greek Cyclades on a three-day adventure with Oscar Private Sailing. Discover secluded beaches, pristine waters, and timeless island charm—perfect for a memorable maritime escape.
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.
Plan for shaded and sunny spots
Bring sun protection and comfortable clothing for variable weather during sailing days.
Book early for peak season
Secure your spot in summer months early as this trip is highly popular.
Bring underwater gear
Snorkels and masks enhance your experience exploring marine life.
Stay flexible with the itinerary
Weather conditions might adjust the route for optimal safety and experience.
Swimwear
Light and quick-drying to enjoy swimming and water activities.
summer
Sun protection
Sunscreen, hats, and sunglasses to stay protected under the sun.
summer
Light layers
Layered clothing for comfort during variable weather.
spring; summer; fall
Waterproof camera
Capture underwater moments and scenic views.
summer