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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.

30

experiences

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4.8

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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64 travellers

Starting from

€650

€722

Per person

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5.0

Super!

Corfu and the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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2 travellers

€711

€790

Per person

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5.0

Sailing WellEssere in Ionian Greece

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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4 travellers

Starting from

€1,215

€1,350

Per person

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4.4

In the Sea of Ulysses among the most beautiful islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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4 travellers

Starting from

€675

€750

Per person

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4.9

Super!

Sailing Cruise in the Ionian Islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€665

€700

Per person

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3.7

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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4 travellers

Starting from

€522

€549

Per person

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4.9

Flotilla in Ionian Greece (sailboats with gennaker)

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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2 travellers

€1,150

Per person

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4.8

Magical Week of Wellness Yoga, Cooking, Health, and Relaxation

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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4 travellers

€1,200

Per person

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4.4

Weekend a Corfù

Duration:

3 days - 3 nights

Greece:

Ionian Islands

Give this experience a try!

€390

Per person

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4.9

Super!

Easter in Corfu

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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2 travellers

€590

Per person

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YogaSail, Yoga Retreat on board a sailboat in the Ionian Islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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9 travellers

€850

Per person

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4.9

One-way flotilla in Ionian Greece from Zakynthos to Lefkas

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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7 travellers

€1,050

Per person

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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.

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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

843 reviews

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Gone with the Wind: Corfu and the Ionian Islands

04/1/2025

jenna C.

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Canada

I was so excited to go sailing in Greece. This dream unfortunately took a quick turn into a nightmare. The captain didn’t take us to any of the sites listed on the itinerary. We stayed close to the original port the whole trip. We would ask him each day to go to one of the listed places and he would just ignore the suggestions. He would also blame it each day on the weather yet we had beautiful weather the whole trip, minus the first day. The boat itself was constantly breaking down. We had a broke toilet which was not a plus. But the worst part of the trip was when the captain used the outside shower in front of myself and a few of the other girls on the boat. He proceeded to take his swim shorts off deliberately flashing his private parts to us. All the lady’s became super uncomfortable on the boat afterwards. It was super inappropriate. Would highly recommended spending your money elsewhere. Was a horrific experience.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

03/23/2025

Matt V.

-

United States

Absolutely phenomenal sailing adventure with Alessandro and Andrea! From the moment we stepped aboard in Corfu with our three children (ages 7, 10 and 12), we knew we were in expert hands. They crafted the perfect itinerary, taking us to the stunning islands of Paxos and beyond, revealing the hidden gems of Greece. Our days were filled with unforgettable experiences: hiking to ancient temples, swimming and snorkeling in pristine bays, collecting sea shells, exploring historic castles, and wandering through charming seaside towns. The boat was incredibly comfortable, making our nights as enjoyable as our days. The meals onboard were all excellent as well and the accomodations were clean and cozy. Alessandro and Andrea's hospitality was truly exceptional. They are not only skilled sailors, but also passionate guides, sharing their love for Greece with us. They even played Uno with our kids every afternoon. Their knowledge and enthusiasm made this vacation one of the best we've ever had. Thank you, Alessandro and Andrea, for showing us the most beautiful side of Greece! You are simply the best! 5 stars without a doubt.
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The alternative to the catamaran in the Ionian Islands

10/15/2024

Belinda B.

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Australia

Best live aboard sailing trip I have done. The boat was exceptionally comfortable and everything clean and in ship shape ! The skipper was great at helping us learn the ropes to participate in the sailing if we wanted to. I loved having the SUP and snorkel sets on board to use when we moored in beautiful bays. It was terrific to catch fresh fish to eat along the way too. Thanks so much to Manuele for making my first trip to Greek Is such a wonderful experience.
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

10/7/2024

Lorenza G.

La barca è molto accogliente e ben tenuta. Lo skipper molto competente, disponibile e rassicurante. Abbiamo navigato a vela e fatto bellissimi bagni nonostante il meteo non sia stato dei migliori. Esperienza da consigliare.

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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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