Our Private Cruises
Based in Milos, a wonderful island located in the South-West of the Cyclades archipelago, OscarPrivateSailing offers its clients a wide choice of cruises. Whether for a daily cruise or more, we make it a point of honour to personalise each cruise according to the desires of our guests in order to make it an unforgettable experience. Contact us to organise your next trip !
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Our Shared Cruises
Departing daily from Kimolos, our shared sailing cruise takes you to the stunning Blue Lagoon of Polyaigos and other beautiful secret swimming spots in the Aegean. With two departures every day, a maximum of 12 guests onboard, and a selection of traditional Greek meze served during the cruise, it offers a relaxed and friendly sailing experience. Join us to discover crystal-clear waters, breathtaking scenery, and the authentic hospitality of the Cyclades.
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Ryan W
November 2, 2022.
Excellent experience
Extremely beautiful cruise with knowledgeable crew! It was windy on the south side of the island so the crew suggested that we depart from the other end of Milos. Great suggestion as we sailed smoothly to 3 other beaches and had an incredible time soaking up the sun and eating delicious food (risotto was amazing)!
JAMSnono105
September 27, 2022.
Dreamy private sailing cruise
We had an incredible, dreamy, peaceful few days (3 days, 2 nights) sailing around Milos and Kimolos with Nikos and Mathilde for the start of our honeymoon. We enjoyed our time aboard the Matilda so very much, from our tranquil naps in the sun to the delicious pasta lunches cooked by Mathilde to our swims around gorgeous island coves and beaches. One night we free anchored off the coast of Milos, and the second night we docked in the Kimolos marina - both were fabulous. Nikos pointed us towards the best restaurants and walking areas so we could experience the islands, but then we got to get back on the boat for the most magical sleeps in our cabin. Nikos and Mathilde took excellent care of us, making us feel at home and relaxed. We will recommend this experience to everyone we know! It was truly a dream.
Anastasios P
September 6, 2022.
Perfect Private Sailing Cruise
My wife and I went chose Oscar Private Daily Sailing Cruise for our honeymoon. We visited Kimolos and Polyaigos. Mathilde and Nikolaos were excellent hosts and we had some great conversations while also allowing us to have some private moments on our own. They took us to some beautiful beaches with very clear water. We were lucky to see an octopus, a turtle, and goats in Polyaigos. They gave us a GoPro camera and shared the photos that we took via usb after the trip. A standup paddle board and snorkeling equipment was also provided. The food that they offered on the boat was delicious and homemade.Amazing experience overall!
Mzambas
September 5, 2022.
AMAZING!
Most amazing experience my husband and I have ever done. One we will always remember and we will be booking this again next trip to Milos. Nikos and Matilda were so kind and so easy to speak to. They made our cruise to kleftiko so romantic and personal and was one of our favorite parts of our honeymoon.
Jeremy D
September 2, 2022.
Brilliant
Fabulous two day trip round the islands with great hosts. Beaches, food, boat and accommodation all good
Robert A
August 30, 2022.
A trully excellent experience highly recommended.
This summer we have spent four wonderful days on board of the Matilda with Nikos and Mathilde. The boat has been very comfortable for the five of us: 2 adults + 3 teenagers. Upon arrival it was impeccable and it remained that way every day on board.Mathilde is charming and a very good cook. She's been always attentive to our needs with a smile. Nikos is a trustworthy captain. He knows the sea, the islands and the wind. He knows where to go and where to avoid tempting fate. Even in some moments when we were able to enjoy real sailing, he always gave us a lot of security even with the wind tilting the boat.Thanks to Nikos and Mathilde we discovered Milos, Polyegos and Kimolos. We would love to board the Matilda again one day to see more wonderful places.
helene h
August 29, 2022.
Magnifique croisière
Superbe journée en compagnie de Mathilde et Nikos, une magnifique croisière.Tous les ingrédients étaient là pour que nous passions des moments merveilleux: découverte de plages, paddle, repas préparé par mathilde....
seanbari
August 18, 2022.
5 STARS
Top notch experience, a must do for anyone visiting the island. Mathilde and Nikos were amazing hosts, made the experience feel like we were family rather than another number in line going on a tour. Don't look anywhere else!
SimoneB12
August 16, 2022.
Amazing Day
We had an amazing day, discovering Kimolos and Poliegos. The wether was amazing and we really enjoyed the cruise. Mathilde and Nikos were really nice, making sure that everything goes perfectly, and it definitely was ! Thank you for the experience
Phil F
August 9, 2022.
Five stars for Oscar Private Sailing
Incredible experience on the sea with Nick and Mathilde, our guides. They showed us the most beautiful beaches in Milos And cooked a fabulous lunch. They were beyond friendly and put our happiness and safety first. Would absolutely come back to visit them and sail on the Matilda next time we come to Milos. It was our favorite part of a long three week vacation in Greece! See you again soon we hope. Thank you!!