7500Nautical Miles
182Happy clients
405 Star reviews
Why choosing Oscar for your cruise ?
  1. Matilda, a 42 feet classic sailing boat

    Matilda, is the name of our 42ft (13m) Bavaria Cruiser. She was our dream and we have made her our summer home on the surface of the sea, a warm and welcoming place for our guests. Nikos is constantly taking care of her, renovating and refurbishing the inside and the outside to make it cosy and practical.

    The inside is composed of 4 double cabins: 3 double beds and a pair of bunk beds. We try as much as possible to keep the forth cabin as a storage room to make people more confortable, store the luggages and equipments when necessary.

    There are also two bathrooms and one outdoor shower for the most adventurous!

  2. Private groups only, kids friendly

    We offer private cruises only, for couples, families or friends. Our guests rent the whole boat and the trip in planed according to the group’s wishes.

    Choose Oscar for your honeymoon trip, wedding proposal, bachelor party or for the graduation celebration of your teens.

    The children are more than welcomed in the boat. The trip can be adjusted to the presence of young kids by sailing smaller distances in protected areas only. Kindly let us know if you are willing to join us with young children so that we can adapt the schedule accordingly.

  3. A tailor-made experience

    We are proud de be able to offer a tailor-made experience for people that want to rid themselves of the inherent stress of modern-day life.

    We like to customise for each cruise, the destination,  the menus, the schedule according to our guests, their habits and preferences. Make your own formula choosing your destination, the duration of the cruise and even the food.

    Regarding the food, our daily cruises include an all-inclusive formula, with food, drinks and snacks all day long. For several days on-board, it includes a half-board formula with breakfast, lunch and snacks during the day. Only dinners, usually taken ashore in any local taverna remain at client fees and are a nice opportunity to enjoy the Greek island’s life in summer.

  4. Experienced crew and local experts

    Nikos is the owner and skipper of Matilda, which he takes care of during the winter. He graduated and obtained his Yachtmaster offshore from the Royal Yachtmaster Academy as well as his cruising instructor certificate in 2022. Thanks to his offshore experiences on the high seas, he is experienced and makes a point of ensuring the safety of the crew. Local expert, he knows the Cycladic islands better than anyone and takes his crew to the most beautiful coves in the region.

    Mathilde will make you feel like home with her kindness and delicious cooking. From France and speaking 4 languages, she is warm and caregiver.

  5. Activities & watersports

    We provide snorkelling equipment for all our guests, a paddle-board, and a large dinghy boat with his out-board engine.

    During long trips, we pull the fishing rot, hoping to catch some fresh fish for lunch.

    For sports enthusiasts, some islands such as Sifnos, Polyaigos or Amorgos offer the possibility to have long walks thanks to their many and well-maintained paths. A morning run is always a good option to keep us in shape during holidays !

  6. Multi-languages cruises

    English, French, Greek and Spanish spoken.


Oscar the sharpei
Mascot and the company's name giver

Born in 2017, Oscar the sharpei is our playful mascot and knows how to melt you heart in half a minute. We decided to make him the founder of the society and he gave his face to our logo.

Hostess & back-office

Friendly, caring and dynamic, Mathilde will make sure everything is perfect on board. She takes care of the cooking, cleaning & helps setting the sails. The comfort of all the guests on-board is her priority.

Captain & Manager

Experienced & qualified sailor, Nikos is certified RYA YachtMaster Offshore and a RYA cruising instructor, owning his 42ft sailing boat since 2019. As a local expert, he knows the Cycladic islands like the back of his hand and sails his guests to the most beautiful areas.



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