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Yacht sailing holidays & skippered tours in the Ionian Islands

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.

  • Sailing Holidays
  • Greece
  • Ionian Islands

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 41 reviews
    confirmed

    Ready to set sail? Magical places await you! - HOSTESSES on board

    from 23 September - 7 nights
    Ionian Islands Greece
    4 people
    are onboard
    640€ Per person
  • 21 reviews

    Gone with the Wind: Corfu and the Ionian Islands

    from 30 September - 7 nights
    Ionian Islands Greece
    2 people interested
    in this holiday
    391€ Per person
  • 7 reviews
    confirmed

    Didactic week on a sailing boat - Ionian Greece

    from 2 October - 7 nights
    Ionian Islands Greece
    4 people
    are onboard
    847€ Per person
  • 18 reviews
    confirmed

    Hidden Ionian - 3 nights

    from 7 October - 3 nights
    Ionian Islands Greece
    3 people
    are onboard
    490€ Per person
  • 10 reviews
    3 discounted
    spots

    Sailboat cruise in the Ionian Islands

    from 7 October - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    583 561€ Per person
  • 21 reviews

    Gone with the Wind: Corfu and the Ionian Islands

    from 7 October - 7 nights
    Ionian Islands Greece
    3 people interested
    in this holiday
    391€ Per person
  • 7 reviews
    4 discounted
    spots

    Educational week on a sailing boat - Ionian Greece

    from 9 October - 7 nights
    Ionian Islands Greece
    2 people interested
    in this holiday
    901 848€ Per person
  • 21 reviews

    Gone with the Wind: Corfu and the Ionian Islands

    from 14 October - 7 nights
    Ionian Islands Greece
    3 people interested
    in this holiday
    391€ Per person
  • 7 reviews
    4 discounted
    spots

    Didactic week on a sailing boat - Ionian Greece

    from 16 October - 7 nights
    Ionian Islands Greece
    2 people interested
    in this holiday
    899 846€ Per person
  • 6 discounted
    spots

    Sailing fun and sports in Corfu and Paxos. Don't miss out!

    from 21 October - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    954 848€ Per person
  • 21 reviews

    Gone with the Wind: Corfu and the Ionian Islands

    from 21 October - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    391€ Per person
  • 7 reviews
    4 discounted
    spots

    Didactic week on a sailing boat - Ionian Greece

    from 23 October - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    898 845€ Per person
  • 1
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Reviews - Yacht sailing holidays & skippered tours in the Ionian Islands

777 reviews
20 / 10
Andrea C.

Andrea C.

review about We enjoy the beautiful islands and Mediterranean cuisine of Ionian Greece August 2023

10 / 10
Just landed and Antonio already misses us. We found not only a skipper but also a friend. A person endowed with extreme sensitivity with the savoir faire of a true gentleman. Great cook as well as wonderful diner, he pampered us with amazing dishes freshly prepared during our stops in the wonderful coves of the Ionian Islands. He also knew how to recommend the best typical trattorias in our stops, also keeping us company in our dinners on the ground. Excellent seafaring experience, prudent and always alert at all hours of the day and night. Extremely attentive in communication, he is the perfect person to go to sea with. The boat is a charming old lady of the 90s, the interiors are perfect, the cabins welcoming and functional. It was our first experience on a sailing boat and it will definitely not be the last, but always with Antonio.
Silvia S.

Silvia S.

review about Ionian Greece: fun in paradise August 2023

10 / 10
It was a wonderful trip with special people, which I will always carry in my heart! Thanks Francesco!
Mattia M.

Mattia M.

review about VELABLU flotilla to discover Ionian Greece on a sailing boat August 2023

10 / 10
A wonderful week: fun, relaxation and for those who wanted to learn.
Carlotta M.

Carlotta M.

review about Sailing week exploring Ionian Greece August 2023

10 / 10
Mario, Sarah, Molletta & Nina are the true soul of their Mary. From all of them you can only learn, love sailing and feel their passion for the sea, nature and above all for what they do. The crew is a family: attentive, competent and dynamic. This is not just a holiday, but an experience of life, sharing and passion. Cruise studied and planned in detail to enjoy the wonder of the Ionian, to regenerate and to live slowly. Mario is patient and competent to always explain in detail and involve the crew. Great food and great places. Thank you for having us on board! We will be back soon ! Good wind ??
Alfredo B.

Alfredo B.

review about Corfu and Diapontie starting from Santa Maria di Leuca August 2023

10 / 10
Definitely positive experience, experienced skipper and very attentive to the safety of the crew. Boat equipped with good comfort - including air conditioning - not easy to find as equipment. Generally positive holiday
Jacques B.

Jacques B.

review about Relaxing week on a super comfort catamaran with a young oceanic skipper July 2023

10 / 10
Nicolo is a young skipper but with lot of experiences He is working hard to increase knowleges in Sailing to do Oceanic Sailing Not in the sailing performance but in cool way that was perfect for this Cruise You can ask what you want in term of places to go He catch Octopus and Oursins for the team.. Gracie Milles Nicolo
Arnaldo U.

Arnaldo U.

review about Kefalonia and Ithaca on luxury new fast catamaran, private bathroom - only 4 guests July 2023

8 / 10
High level boat kept impeccably by the owner (only note the water pump too noisy). We sailed to discover enchanting bays between Kefalonia and Ithaca. Compared to what was advertised I would delete the reference to air conditioning, never used even in extreme conditions; I would also recommend using the desalination plant fluently so that you can have a more frendly relationship with the water on board. Last note, given the gap between the two cabins, a price differentiation would perhaps be appropriate. SKIPPER ANSWER I am glad that Arnaldo also appreciated the high quality of our catamaran and the wonderful holiday spent in search of the most beautiful bays and coves, even if I find some comments not shareable. As for the desalinator (which most boats do not have, thus forcing deviations of the route to recharge the tanks in port once the reserve is over, or washing at sea instead of comfortable showers on the boat, as in our case), it has in fact been regularly used to recharge the tanks, thus ensuring at all times the availability of fresh, hot and cold water, without any solution of continuity, as well as without any effort or problems to procure it; However, as has also been mentioned on board, those who go by boat normally know that water on board remains a precious commodity, even when you are lucky, as in our case, to have a desalinator on the boat; In other words, water is a commodity to be used, but not to be wasted... Yes, yes, all the water you need to feel good (as it was in our case), but without the need to open the taps "throttle", as you can possibly do at home ... Also with regard to the use of air conditioning (also generally rare on other boats), as in all charter contracts, even in our contract (which Arnaldo also signed, I do not know why he did not take it into account in his comment) it is expected that the same can be used (and without limits) in the presence of an electrical connection in port, because otherwise the high power of the system would completely discharge the on-board batteries in a few hours. Since in the ports in Greece there is not always enough voltage to power an air conditioning system (it depends on the place where you are), the use of air conditioning does not depend on the Skipper, but on the characteristics of the port or marina available from time to time. All this was also explained on board, and Arnaldo seemed to have understood, without adding any comment or request at the time; I am therefore surprised by this posthumous observation, as well as being unfounded in its content. In any case, despite the climatic situation in mid-July was, as known, exceptionally hot throughout Europe, thanks to the excellent natural ventilation of the boat (the cabin used by Arnaldo has, for example, two large ceiling walkways, which is quite rare in the nautical panorama), and the excellent fans supplied, even when it was not possible to use the air conditioning for the reasons explained above, On board we slept well, however. Finally, as far as the cabins are concerned, they are both of a very high standard and very comfortable, all with private bathroom and shower. One of the two cabins is larger and with ensuite bathroom, although smaller, the other cabin has a larger bathroom, although not ensuite and a larger bed. Everything is also clearly shown in the video attached to our ads. Each cabin therefore has its strengths and guests in general appreciate both cabins indifferently, without distinction. Finally, I regret that, beyond these comments, which I find precisely not acceptable, Arnaldo has not instead reported, among the various things he has been able to experience on board, the courtesy and assistance constantly received to maximize his experience, including, as a mere example, the pharmacological assistance we provide spontaneously - without even receiving a request and thanks to the rich equipment that we keep on board for the safety and comfort of our guests - thanks to which Arnaldo has solved a specific health problem of his partner, thus avoiding having to walk remotely to a pharmacy and during the hottest hours of the day.
Catalina  S.

Catalina S.

review about Lefkas, Kefalonia and Ithaca on a 17m boat - Chef on board July 2023

10 / 10
Renato is a great skipper, competent, thorough, willing to teach and transmit his love for the sea. Lulù is your perfect complement and an excellent cook!
Petra T.

Petra T.

review about Discovering the Ionian islands in Catamaran with Hostess July 2023

10 / 10
I had an amazing week with Michela & Luca sailing Ionian islands. They are lovely people, wonderful personality, fun, easy going and caring. We mostly anchored in beautiful bays immersed in nature and were under the sails several times on the trip which was very cool. Michela cooked delicious and fresh meals (she brought some very special and quality ingredients from Sicily with her) and took a great care of all the guests! Can't wait for next trip with this great couple! Crazie mille Michela & Luca!
Sonia F.

Sonia F.

review about Athens Kefalonia via the Corinth Canal: exceptional! May 2023

10 / 10
The boat is challenging, but everything is done in absolute safety. Thanks again to Antoine and Fides for the miles spent together to enjoy wind, sea, sun, teachings and good company
Barbara P.

Barbara P.

review about Sailboat cruise in the Ionian Islands April 2023

10 / 10
The three of us had a wonderful trip to delightful little Greek harbour villages. Bertrand was always concerned about our safety. We felt absolutely 'in good hands'! Paxos, Gaios, Syvota, etc. , excursion with rental car to Parga, absolutely worth seeing. Despite the pre-season, Betrand always knew which taverns would prepare good food for us. We had very nice weather, always blue skies with stormy winds from time to time, sailing weather. However, bathing was still very fresh, wetsuit / bathing shoes at this time of year is recommended. Bertrand is a very competent skipper. This trip is highly recommended! Greetings Barbara
Daniel P.

Daniel P.

review about Corfu - Paxos - Anti Paxos - Parga September 2022

10 / 10
We had an amazing experience traveling with Giovanni and his wife, Stefania. They were such a charming couple, funny and lovely. We had the greatest experience of our greek holidays. They know the best places to eat, to swim, to relax… highly recomended!! We already miss them!
David F.

David F.

review about Ionian Greece: on a sailing boat for 10 days with skipper, staff and galley service August 2022

10 / 10
Superb experience! Well organized, good equipment, very good selection of itinerary, great staff, fantastic crew. Can definitely be highly recommended and will repeat in the future.
Stefania A.

Stefania A.

review about Sailing cruise to the Ionian Islands August 2022

10 / 10
Andrea and Kikka made our cruise unforgettable! Andrea is a great commander and with his thirty years of experience he entertained us with the stories of his many crossings and gave us a navigation with many sailings always in maximum safety making our experience exciting. Kikka pampered us with the onboard kitchen. Thanks to his expertise he taught us the rudiments of sailing and gently complied with our every need. I will definitely do other cruises with them.
Germano A.

Germano A.

review about Ionian Greece sailing in absolute relaxation with all comforts July 2022

8 / 10
I would say it was a beautiful holiday, all expectations were met. Maurizio is definitely a great example of Skipper!
Isabel B.

Isabel B.

review about Sailing course and discovery of Ulysses' Greece - Ionian Islands July 2022

10 / 10
Great and skilled skipper who is focussed on teaching sailing, building group confidence and communication and experiencing nature. A great alternative to party tourism and luxury cruises - we stayed in wild bays for 6 nights which was extremely relaxing! I started from a level of no experience whatsoever and learned a lot while enjoying the stunning landscape of the Ionian Islands. Emmanuelle was very attentive and flexible to our needs and ideas for the route and also a great company for the trip! It was also particularly amazing as a non-male person to travel with a female skipper of whom there are too few! Highly recommended, already looking forward to our next trip.
Pierre S.

Pierre S.

review about Sail with us under the Greek sun in its paradise islands July 2022

10 / 10
Excellent stay with Sabine and Patrick around the Ionian Islands. They are very accommodating and will do their best to make you have the best possible stay according to your desires. Go there with your eyes closed!
Stefano S.

Stefano S.

review about Set off to discover the Ionian islands with the gastronomy of Davide, your skipper cook! June 2022

8 / 10
ON HOLIDAY WITH A SPECIAL PERSON My holiday with Davide was a nice holiday. The boat is wide and comfortable. The skipper a special person, sailor, chef, man of the world, a friend... The cruise was pleasant even if there was little wind in the area so mainly motorized. The places, especially PAXOS and ANTIPAXOS very nice. We traveled in a group of three boats for which the company was not lacking. Every day for lunch a Greek or Neapolitan dish cooked with skill. What can I say? I recommend it.
Silvia V.

Silvia V.

review about All Inclusive cruise to the Ionian Islands with hostess. Relax, we'll take care of the rest! June 2022

10 / 10
There would be so much to say but I will be short and engraved: the captain the skipper indeed both multipurpose 2Shores careful you have needs and the protection of the crew. 2 excellent cooks other than to be 2 cultured and very pleasant people . Thanks hard not to get attached . Silvia
Eeva V.

Eeva V.

review about May Bank Holiday from Corfu to Sicily, sea, sun and wind all for you! April 2022

10 / 10
We had a fantastic sailing week exploring the Northern Sicily and Eolian Islands Lipari and Volcano. Mark is a competent and professional skipper. The ambience in the shipshape boat is forthcoming and relaxed. We enjoyed good food, music and sailing. Happily recommended!
Norbert M.

Norbert M.

review about Are you a lover of nature and crystalline seas? This is the perfect relaxing holiday April 2022

10 / 10
Hello We had the pleasure of sailing with Alessandro. He is a very friendly boy who was very caring for us. Always wondering if everything was okay and if we needed anything. He knows the island of Corfu and its history very well. The meals prepared by himself, of local types were delicious. In addition we had the chance to be accompanied by his brother Andrea who usually pilots another boat and who is older and just as pleasant as his brother. We spent a very nice week in their company and are thinking of renewing the experience at a more summer time to enjoy swimming. I highly recommend this mini cruise especially with these two young people in love with nature, the sea and their job as sailors because we feel that it is really a passion for them.
Silvia A.

Silvia A.

review about Sailing in the footsteps of Ulysses! 7 days to discover the Ionian islands with hostess on board September 2021

8 / 10
Great nice holiday! Splendid itinerary with stops in quiet coves and crystal clear sea. Relaxing holiday on a large and very comfortable boat!
Cristina F.

Cristina F.

review about Kefalonia, Itaka and Zante at full speed !! August 2021

10 / 10
Claudio is a very prepared skipper, always attentive to safety and everyone's needs. He allowed us to visit magnificent coves where only we were. It was an incredible week and as a first sailing experience I couldn't have asked for better. Thanks Claudio!
Sveva C.

Sveva C.

review about On the route of Ulysses sailing! Ithaca, Zakynthos, Kefalonia in a splendid Oceanis 46.1 of 2020 !! August 2021

10 / 10
Mattia is the best skipper with whom I have ever sailed: always very attentive and scrupulous with a great sense of responsibility and passion for sailing, despite there have been moments of sea and strong wind I have always felt calm. He is always in a good mood (amazing) and working to plan the perfect day for everyone

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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.

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