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Yacht sailing holidays & skippered tours in the Ionian Islands

The Ionian Islands lie in western Greece, and are composed of twelve small and large islands, including Zakynthos, Ithaca, Corfu, Kefalonia, Lefkada, and Paxi. Here, lush vegetation, striking landscapes, and the turquoise sea combine to create an ideal sailing destination.

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The world's largest marketplace for sailing holidays

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Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

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Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in the Ionian Islands

897 reviews

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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/8/2025

Domenico F.

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Italy

Andrea is a very prepared skipper, he showed us beautiful places despite the bad weather made us change the itinerary a bit, he recommended a lot of typical taverns with delicious food and was always available for any kind of need. Marta did not let us miss anything, excellent breakfasts and lunches, far too helpful. There was a bad storm in Corfu on the first day and they delayed the departure by a few hours so as not to make us miss the holiday. I would say everything perfect
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From Corfu sailing between turquoise sea and white beaches - hostess on board

09/8/2025

Ignacio G.

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Spain

We are a family of 4, two kids under 12, and our experience could not have been better. Omar and Enrica are a great team that take care of you sailing and in the boat. We enjoyed beautiful locations where they made their best to arrive at times where we could be (almost) alone. They also ensured we could do nice sailing and visit beautiful locations. Also their cooking on the boat was great! healthy and delicious! Last, but not least, boat is super nice and well taken care of. We will do our best to do some more sailing and, for sure, we will call them back!! Strongly recommended as friends and/or family. Definitively worthy.
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/1/2025

Cinzia S.

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Italy

I spent an unforgettable week sailing in the beautiful area of Lefkada. Breathtaking landscapes, bays with crystal clear water and sunsets that look like paintings: an experience that will remain forever in my memories. A special thanks goes to skipper Francesco, who with professionalism, passion and sympathy made the holiday even more unique. Always attentive to the needs of the whole crew, he guided us safely to discover hidden corners and made us feel at ease from the first to the last day. I recommend this experience to anyone who wants to experience the sea in freedom and relaxation, with the certainty of being in excellent hands. Thank you Captain
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

08/31/2025

Livio L.

I have had various sailing holidays: Francesco is certainly among the most experienced and prepared skippers I have met, we have done splendid sailings and he has taken us to beautiful places for swimming and relaxing roadsteads. Defects? Bring an alarm clock 😉 Thank you for everything and fair winds!

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  • A mild climate, with good sailing conditions from April through to November.
  • One of the most popular destinations in the Mediterannean for both skippered and flotilla sailing holidays.
  • Experience the culture and heritage of the Ionians with visits to the mediaeval castles, monasteries, and numerous museums.
  • The iconic rolling hills of olive and cypress trees present throughout the lush Ionians.
  • It’s jagged coastlines are truly unique. Once, the Ionians were in fact part of Central Greece, before seismic activity shifted the landscapes.
  • Taste the special local delicacies of the Ionians, such as Pastitsádais, a Greek traditional pasta dish that is prepared on the island of Corfu, or the Lefkadítiki ladópita (oil pie) that originates from Lefkada.
  • See the elusive monk seals and Loggerhead turtles native to the area.
  • Visit one of the European hubs for kitesurfers and windsurfers, with many areas and facilities for various watersports.

The best destinations to visit during your sailing holidays in the Ionians:

The beaches of Engremni, Porto Katsiki, Kathisma on Lefkada, and Shipwreck beach of Zante are spots in the Ionian that have garnered an international reputation. However, there are beaches such as Voutoumi and Vrika on the quieter islands of Paxi and Antipaxi that are beloved by sailors. Then there are the picturesque beaches such as Myrtos, on Kefalonia that is sheltered by a range of towering cliffs, and Corfu’s much-loved Paleokastritsa beach.

The world famous beaches of Engremni, Porto Katsiki, Kathisma on Lefkada

Kefalonia, home to the Assos and its Venetian castle, as well as the ancient towns of Argostoli and Lixouri is also blessed with the natural wonders of Drogarati, the 150 million year old cave system, and Melissani the underground lake. Zante, which was selected as Greece’s first marine park, is in fact the area the rare and endangered caretta caretta turtles come from the Libyan Sea to lay their eggs. Corfu is home to the popular islets of Vlaherna and Pontikonisi (Mouse Island), Sidari (and its Love Canal beach), Paleokastritsa, Kassiopi, Lefkimmi - and it’s capital, the beautiful Corfu town, which is steeped in much cultural history.

An array of natural beauty: Kefalonia, Zante, Corfu, and much more

The Maistro or Maestral is the prevailing northwest wind that flows through the Ionian is much calmer than the Meltemi in the Aegean. Weather conditions are well forecast, the climate is warm throughout much of the year, and the mountainous landscape offers a dramatically stunning backdrop for an ideal sailing experience. All of the above possible with convenient travel routes from major European cities.

The magical Ionian: its climate, landscapes, and locations crafted for sailing

The Maistro or Maestral is the prevailing northwest wind that flows through the Ionian is much calmer than the Meltemi in the Aegean. Weather conditions are well forecast, the climate is warm throughout much of the year, and the mountainous landscape offers a dramatically stunning backdrop for an ideal sailing experience. All of the above possible with convenient travel routes from major European cities.

Tips to help you to better plan for your next sailing holidays in the Ionian Islands:

All you need to know about your next cruise around the Ionians aboard a sailboat.

  • As the region boasts a warm climate for much of the year, sailing the Ionian is recommended between early April and late October.
  • From major European airports there is much availability to the airports in Corfu, Kefalonia and Zakynthos, and several ferry options from Venice, Ancona, Bari and Brindisi in Italy.
  • You can find experiences for a week in the Ionian Islands with a skipper from €450 per person. This figure excludes transport to and from the holiday. It is important to remember that depending on the month of travel and style of boat pricing is subject to change.

The best sailing itineraries for your next holiday with a skipper in the Ionian Islands:

    Corfu and Paxos

    Corfu and Paxos are not only some of the most beautiful areas for sailing in the Ionian, but in the whole of Greece. Many skipper suggest routes including these two areas along the western coast of Greece. With a 7 day trip, it is possible to hop from island to island between popular spots including: Othonoi, Corfu, Merlera, Paxos, and Antipaxos. However, with a longer, more comprehensive trip other areas, there will be more opportunity to explore Corfu, along with other charming areas such as the Syvota islets.

    A wide range of options

    The area offers a relaxing sailing environment, with nature-rich bays, and stunning turquoise waters. Some areas of beauty that local skippers like to include in sailing holidays in the Ionian include: Lakka, Gaios, Mongonisi, Emerald Bay, Two Rocks Bay, and Parga. The wide variety of options in the area, means that with skippers you may be able to heavily customise itineraries to construct a holiday that suits best your wishes.

    Sailing holidays in the Ionian Islands - why you should travel with a local skipper

    If you want to fully enjoy your sailing holiday in the Ionians with the best conditions, we recommend that you go choose a trip with a local skipper. Travelling with a skipper who has insider knowledge on the area, allows travellers to fully immerse in the pleasure and relaxation of the holiday. Where individuals on the trip wish to learn or practice their sailing skills, skippers will be there to integrate travellers into the responsibilities onboard.

Ionian Islands: the best travel ideas

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