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.

FLEXIBLE CANCELLATION.

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

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Two people with sailor hats

Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

A boat with a magnifier above it

Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

Two coins with a currency on top

Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

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

680 reviews
20 / 10
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!
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.
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.
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.
Caterina G.

Caterina G.

review about Sun & Fun Marmaglia Flotilla - 5 Boats in Ionian Greece August 2021

10 / 10
Raffa is the perfect skipper! Calm, never too intrusive or over the top, in short, in the meantime it transmits tranquility and confidence, which on the boat - especially for those who are at the first experience - is important. As soon as I saw it seemed to me the dj Luca Agnelli, oh well just a little lower ????. He is a sunny and sociable person, with whom you can talk about everything and it was nice to enter his world. He never shied away from partying with the crew at any time, with the excuse that he went out of his way to keep us entertained. Raffa, made us discover some wonderful coves. In short, I recommend him, for that calm madness of his.
Leo L.

Leo L.

review about In the sea of Ulysses with the sport you want! August 2021

10 / 10
Expert skipper, great historical, political and social culture of Greece. He knows all the excellences present in the territory, a great connoisseur of wines and typical foods. Great cook and organizer. He was a great colleague for organizing holidays out of standard.
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!
Antoine P.

Antoine P.

review about Surf live east! Galley included on board! August 2021

6 / 10
Renato is doing his best but at his age it's not that easy anymore (I sincerely think he's - a lot - over 62). The boat is comfortable but would need a facelift, like its captain! help with maneuvers is not easy if you do not understand Italian, because English is succinct. Otherwise nice navigation and meals, nice corners and favorite for Alakka.
Aleksandra K.

Aleksandra K.

review about By catamaran in the heart of the Ionian Islands July 2021

10 / 10
Our week on Vincent's catamaran was great! Vincent is really good captain, with a lot of experience, you can learn a lot if you want - do things on the boat - or not, depends from you. He will explain everything (he also has a groups for sail training). Apart from this, he is a really interesting person with many great stories from his life, really easy going and with good recommendation always. Normally at night you can have a dinner in a restaurant, on your own or go with the captain and the rest of the crew, we always chose the second option, as dinner with them was great and the selection of the place perfect! Melanie, his partner, was helpful, and funny! You just have great time with her! And a lot of ice-creams :) The boat is comfortable, and they do not take more than 4 people although there is one cabin unocupied so the group is more comfortable. The area of Ionian Islands was above our expectations. Wonderful views, really beautiful places with clear water. I recommend it!!!
Roberta C.

Roberta C.

review about Visit the islands of Greece with a beautiful boat and the experience of those who have lived there for years! July 2021

10 / 10
The most relaxing trip of my life. If you really need to unplug, without getting bored, a week on a sailboat is for you. Relaxation, rest, contact with nature, music, wind, water, silence, music, colors, adrenaline, good food, sharing, new experiences: find everything. Fabio is an experienced skipper, he knows the area well, he integrates into the group being a very easy-going and nice person; knows how to create beautiful atmospheres. I really think that next year another sailing tour will not hurt me :D
Claudio P.

Claudio P.

review about The Greece of the myth on a sailing boat. July 2021

10 / 10
For us it was the first sailing experience. We never expected to live such an intense and unforgettable adventure. In the amazing setting of Ionian Greece we spent an intense and at the same time relaxing holiday between dream beaches and unspoiled islands. Pino was absolutely fabulous, making the experience even more incredible with his sympathy and with his knowledge of the most evocative and fascinating places. He is a person who accompanies us on a journey to discover unknown and mysterious landscapes, flavors and smells.
Federica M.

Federica M.

review about The fantastic Ionian islands July 2020

10 / 10
More than a holiday, a real experience. Alessandro was a wonderful and helpful captain, decisive when needed, very competent and able to instill security in every situation, excellent chef, of great company but also very discreet. With the children he was kind and patient. For most of us it was the first boat experience and it was just as we expected: bays and coves to take your breath away, wind and silence when we went sailing, sunsets and aperitifs, dinners under the stars, baths at 7 am, incredible sunrises ... we experienced the sea without limits. The children (6 and 7 years old) were little sailors always safe and still carry this wonderful experience in their hearts. We close with a sentence that came out during the navigation: "The Perfect Holiday? The one on a Sailing Boat!". Thanks Alessandro and see you soon!
Federico G.

Federico G.

review about In the footsteps of Ulysses ... August 2020

10 / 10
Exceptional holiday! We visited everything you could see, the boat is very comfortable and has everything you need. Stéphane was very kind, very nice and with a great knowledge of the place. I particularly enjoyed the formula with breakfast and lunch included. The price was a bargain.
Claudia G.

Claudia G.

review about By boat between Kefalonia Ithaca and Zakynthos August 2020

10 / 10
What can I say? Gianfranco is an exceptional captain with great experience, a real sea wolf, an excellent skipper, a perfect chef and a good Romagna jovial and very hospitable person. His boat is absolutely comfortable, spacious and well maintained...... and then there is the crystal clear sea that is the master. Good wind!!!
Luca P.

Luca P.

review about Ulysses' course, August 2020

10 / 10
Skipper and catamaran Top, equipped with every good of god... Sup, canoe, diving equipment etc ... Fabio in addition to an excellent preparation is very good at teaching a little sailing to those interested, it seems strange, but in Charter it is a rare thing. Recommended for those who want to spend a week of relaxation in the name of sea sailing and lots of nature. Do not forget the cute Jack, the delicious sailor dog, always looking to be pampered by everyone, the mascot of the boat!
Trustpilot

Customer Support

Would you like some support using the platform? We've (almost) always got the answers!

Call us at +44 20351 44220 Check out our Help page

Can't find the perfect holiday for you?

Use our free holiday concierge tool - and let us find your dream sailing experience for you!

Let's find it together!

  • 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: best travel ideas

Other travel ideas