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Skippered Sailing Holidays in Greece isn’t just about the destination, it’s about the journey across endless horizons.

Come and sail with us for an unforgettable time.

Skippered Sailing Holidays in Greece

At Sail & Discover, we create private sailing holidays in Greece designed around people, not packages. Since 2011, we’ve been sharing our passion for sailing and the sea through authentic, small-scale sailing experiences in the Ionian Islands. Whether you’re looking for active sailing holidays in Greece or prefer the comfort of private Greek yacht holidays, our skippered sailing experiences are tailored entirely to you.

We believe sailing should feel personal, safe, and inspiring. With a professional skipper, a comfortable yacht, and flexible itineraries, you can enjoy Greece from the water while focusing on what matters most — freedom, connection, and unforgettable moments at sea.

Why choose us for your Greek sailing holidays

  • Private skippered sailing holidays in Greece
  • Active sailing or relaxed yacht cruising — you choose
  • Personalised itineraries in the Ionian Islands
  • Ideal for couples, families, and friends
  • Real sailing experience since 2011
  • One yacht, one crew, one personalised journey
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Stephan & Yuliia so happy to have embraced their livestyle. Come and join us for an unforgettable sailing holidays - Skippered Sailing Holidays in Greece

From quiet anchorages and turquoise bays to charming island villages, each sailing holiday is shaped by your preferences. With Sail & Discover, you don’t join a crowd — you step aboard a yacht where time slows down and every day brings a new horizon.

Explore the Ionian Islands by private yacht

  • The entire yacht just for you.
  • You are setting the course and the pace.
  • Three double cabins are available for a group of up to 6 persons.
  • Ideal for families, family reunions or group of friends.
  • You can be as free as possible.
  • A relaxed sailing vacation — no need to worry about groceries or meals! 
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Sailing into a perfect sunset with Chronos I Skippered sailing holidays in Greece

Personalized sailing itineraries

  • Flexible departure and return points from Preveza, Corfu or Kefalonia
  • Return itineraries
  • One way itineraries
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Itineraries Ionian Islands I Sail and Discover

Read our Greek sailing holiday reviews

Mireille C.

A wonderful cruise in Corsica, a round trip from Ajaccio to Bonifacio. Magnificent scenery and sunsets.. A very warm welcome and helpful staff, and delicious meals! Thank you, Yuliia! An incredible family adventure!! An introduction to sailing, discovering Corsica… and plenty of swimming. Our three teenagers came back with their heads full of memories! Thanks
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Family sailing holidays

Marie de R.

Had an absolutely unforgettable week with Sail & Discover and the ever-amazing Skipper Stephan! From our starting point in Preveza, we charted a course around the picturesque Ionian Islands that seemed straight out of a dream. Night skies lit with shooting stars, playful dolphins racing alongside our boat, and the serene sight of sea turtles
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Family sailing holidays

Vicky Victoria P.

It was such an unforgettable experience for us! We spent our honeymoon on the boat and Stephan has been an amazing skipper..well experienced and took us to nice places for swimming ..Paxos,Meganisi,Parga and Preveza! All the conditions were met to spend a dream vacation. It is possible both to learn how to sail or sunbathing
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Single couple sailing holidays reviews

Al P.

An unforgettable experience. Everything was perfect for a dream vacation. There were six of us on the boat, which was ideal. It was possible to both learn to sail and simply relax on deck. Thank you to Stephan for his idyllic itineraries and his magnificent sailboat. Al

Group of Friends sailing holidays

Florence P.

We’ll cherish the wonderful memories of this cruise to Corfu! We had complete confidence in Stephan, who was discreet, always available, and incredibly calm! We almost forgot we didn’t know him before boarding the boat… Promise, Stephan, you’ll have milk with your cereal next time, and with a bit of luck, you might even get
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Single couple sailing holidays reviews

Constance L.

Fantastic sailing experience! Stephan is an excellent skipper, friendly and professional. We simply followed his advice regarding the itinerary (departing from Preveza, then Lefkada, Kastos, Meganisi…). It was amazing: anchoring in magnificent coves, swimming in tranquil bays, lunches at sea in a breathtaking setting… The atmosphere on board was fantastic! Constance (Translated from french)

Group of Friends sailing holidays

Patrice C.

A very successful week exploring the islands around Corfu. Excellent sailing and lively evenings in the harbors. A great opportunity to learn or improve your sailing skills. The skipper and assistant were very attentive, ensuring everyone had a wonderful time. Patrice (Translated from french)

Family sailing holidays

Jean-yves D.

A dream cruise in the Aeolian Islands with Stephan, an exceptional skipper who introduced us to sailing and the beauty of the islands while remaining attentive to our wishes. A huge thank you. Jean-yves (Translated from french)

Family sailing holidays