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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

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

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

855 reviews

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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/30/2025

Gilberto B.

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Italy

Alessandro, Carlo, Andrea e Marta sono andati oltre ogni possibile aspettativa regalandoci una settimane di relax, incantevoli spot nello ionico, deliziosi pranzi a bordo e fuori. Abbiamo trovato disponibilità, sensibilità e accoglienza fuori dal comune. Barca pulita, ottima comunicazione e organizzazione. Nessun dettaglio lasciato al caso, una vacanza indimenticabile!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/29/2025

Chiara M.

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Italy

Esperienza assolutamente indimenticabile! Sia lo skipper Alessandro che lo steward Carlo sono persone fantastiche e si sono dimostrati sempre estremamente professionali e disponibili. Il viaggio era organizzato perfettamente, proponendo una varietà incredibile di spiagge e attività. I consigli sui locali migliori in cui cenare non sono mancati. Consiglierei a tutti di vivere questo viaggio perché è un mix perfetto di avventura, relax e divertimento con persone speciali. Grazie di tutto, alla prossima!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/29/2025

Julia E.

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Italy

Non potevo chiedere di meglio dalla mia prima esperienza in barca! Ho viaggiato con un altra coppia di amici e le altre persone le abbiamo conosciute arrivate a Corfù, ci siamo trovati subito bene sia tra noi che con Alessandro il nostro skipper e Carlo il nostro fantastico steward che ci ha viziati a dir poco! Ogni giorno un programma studiato e una nuova zona da esplorare, ma non sono mancati i momenti di relax e di meritato stacco! Mi sento davvero fortunata ad avere vissuto l’esperienza e che tutto sia andato così perfettamente, non ho sofferto nemmeno una volta il mal di mare (cosa di cui normalmente soffro) ! Se volete una vacanza in cui vedrete spiagge meravigliose, mangerete in ristoranti deliziosi, farete escursioni con vegetazione rigogliosa e vi divertirete con attività acquatiche di vario tipo, mentre vi state vivendo l’esperienza del soggiorno in barca questa fa per voi! Grazie ad Ale Carlo e tutta la ciurma ! Ci siamo trovati proprio benissimo ! Consigliatissimo !
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

06/26/2025

Debora Z.

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Italy

La mia prima esperienza in barca a vela é stata meravigliosa. Andrea è Marta sono molto professionali e seri sotto l'aspetto della navigazione e al contempo sanno intrattenerti con attività diverse ogni giorno, posti speciali, aneddoti e manicaretti buonissimi. Sanno creare gruppo tra le persone e sono sempre disponibili per aiutarti in eventuali esigenze. Non potevo chiedere di meglio: esperienza oltre le aspettative!

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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

Other travel ideas

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