header cover
logo

Log in

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.

cover image
avatar image

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

cover image
avatar image

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

cover image
avatar image

4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

€600

€540

Per person

cover image
avatar image

4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

cover image
avatar image

4.8

Super!

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

3 departures available

August - October

Starting from

€900

Per person

cover image
avatar image

5.0

Super!

Catamaran week among the islands of Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

One departure available

September

€1,125

Per person

cover image
avatar image

4.8

Super!

Following the North Star: From Kefalonia to Corfu

Greece: Ionian Islands

6 days - 7 nights

One departure available

August - September

€650

€585

Per person

cover image
avatar image

4.5

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

cover image
avatar image
Ionian Escape – Sailing Week from Corfu – Paxos & Antipaxos

Greece: Ionian Islands

7 days - 7 nights

One departure available

August - September

€800

Per person

cover image
avatar image

New

Corfu: sailing, dream bays and walks in the villages - hostess on board

Greece: Ionian Islands

6 days - 6 nights

9 departures available

August - October

Starting from

€1,200

€500

Per person

cover image
avatar image

New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€1,645

Per person

cover image
avatar image

New

Premium

All inclusive catamaran cruise on a Bali 4.2 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

3 departures available

August - October

Starting from

€2,060

Per person

Why book a holiday with Sailsquare?

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

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

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

1021 reviews

avatar image

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

08/27/2026

Sandra M.

-

IT

The holiday with Andrea was perfect! Andrea is a very good skipper, who makes guests feel at ease with simplicity, always kind and helpful, generous in making the most beautiful bays and beaches known by tender, where we have experienced unforgettable baths and moments. Very clean boat thanks to Carol, the hostess, who in addition to taking care of the spaces, prepares really good breakfasts and lunches, with the added value of having tasted typical Greek dishes. The travel program was nice, I enjoyed dining on land and visiting the delightful villages along the itinerary, it made the holiday even more varied and complete. After many years of sailing holiday, this experience has stood out for its organization, care and quality of service. Thanks to Andrea, Mattias (the loving poodle who conquers everyone) and Carol for the beautiful week. Super-recommended!
avatar image

Different flotilla in Ionian Greece: nature, new friends and fun

08/27/2026

Jacopo A.

-

IT

Fantastic experience. Our skippers and co-skippers Vincenzo and Nina were great, helpful, fun and very professional. Beautiful places and lots of fun.
avatar image

Come and try sailing in Ionian Greece

08/27/2026

Barbara R.

I had the privilege of being on the boat with Angelo. Evenings spent on board with a glass of beer in hand, the sound of the guitar in the background and his life stories capable of enchanting. Angelo is an acute observer, endowed with an overwhelming irony. Beneath the surface of the always ready joke, one senses a deep sensitivity. On the one hand, the boundless passion for the sea and sailing, lived with energy and freedom, on the other, the intimate story of a man who learns to know himself step by step together with the sea. Highly recommended for those who love the sea, music and true stories told in the roadstead. Barbara

Different flotilla in Ionian Greece: nature, new friends and fun

08/27/2026

Giusy M.

-

IT

A beautiful sailing experience, made special by the sea, by the days spent together and above all by the people we met on board. A fun and intense holiday, which allowed you to really disconnect from the routine and spend days in a different and authentic way. A special thanks to skipper Roberto Trinari, who with his experience has been able to convey to all of us the passion for sailing, teaching us many useful things and making us experience the sea in an even more authentic way. His availability and enthusiasm helped make this experience even more beautiful. A special thanks also to co-skipper Antonio Testa who, despite being at his first experience in this role, has always been available and attentive, contributing enthusiastically to the success of the holiday. A holiday that I will remember with pleasure and that I recommend to those who want the sea, sailing, fun and good company. ⛵️❤️

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

  • 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

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964