Set sail from Pollonia into the hidden gems of the Cyclades with Oscar Private Sailing. Discover uninhabited islands, snorkel turquoise waters, and savor fresh Greek cuisine—all in one unforgettable day.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
8 hours
Fitness Level
Suitable for most fitness levels; moderate stamina recommended for swimming and extended boat time.
Wildlife
History
The Cyclades islands have been inhabited since antiquity, with ancient maritime routes shaping local culture.
Conservation
Efforts here focus on protecting marine biodiversity through sustainable tourism practices, including responsible anchoring and waste management.
Oscar Private Sailing
Set sail from Pollonia into the hidden gems of the Cyclades with Oscar Private Sailing. Discover uninhabited islands, snorkel turquoise waters, and savor fresh Greek cuisine—all in one unforgettable day.
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.
Bring waterproof gear
Use a GoPro or waterproof phone case to capture underwater moments without worry.
Pack a light change of clothes
Swimwear, towel, and a cover-up are handy for quick changes after swimming stops.
Apply reef-safe sunscreen
Protect marine life and your skin during prolonged sun exposure on the deck.
Bring your camera or smartphone
Capture photos of stunning coastlines, marine life, and memorable moments.
Swimwear
Comfortable swimwear for swimming and sunbathing.
summer
Sunscreen (reef-safe)
Protect your skin and marine ecosystems during sun exposure.
summer
Waterproof camera or GoPro
Capture underwater scenes and scenic views.
Hat and sunglasses
Shield your eyes from the strong Mediterranean sun.
summer