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Sailboat yacht sailing holidays & tours in Ionian Islands

Discover more than 20 opportunities to get on board a Sailboat adventure in Ionian Islands. A unique experience with a local skipper, starting at €350 a week.

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€550

Per person

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4.9

Super!

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

Greece: Ionian Islands

7 days - 7 nights

10 departures available

July - October

Starting from

€550

Per person

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5.0

Super!

Corfu and the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

July

€790

Per person

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4.8

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

Greece: Ionian Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€600

€540

Per person

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3.7

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Greece: Ionian Islands

6 days - 6 nights

10 departures available

July - September

Starting from

€500

Per person

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5.0

Super!

Seven days in the blue on the trail of Ulysses

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,000

Per person

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4.9

Super!

Corfu - Lefkada ONE WAY: an exclusive adventure with hostess on board

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€464

Per person

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4.9

One-way flotilla in the Ionian Sea from Lefkas to Zakynthos

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€1,150

€950

Per person

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4.3

Premium

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

Greece: Ionian Islands

7 days - 7 nights

12 departures available

July - October

Starting from

€835

€752

Per person - min 2 pax

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A week from Kefalonia to Zakynthos, Ithaca and neighboring islands.

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€700

Per person

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5.0

Seven days in the blue on the trail of Ulysses

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,000

Per person

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4.3

In the Sea of Ulysses among the most beautiful islands

Greece: Ionian Islands

6 days - 7 nights

6 departures available

July - August

Starting from

€860

€774

Per person

Why book a holiday with Sailsquare?

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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 - Sailboat yacht sailing holidays & tours in Ionian Islands

797 reviews

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

07/7/2025

Diana U.

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Italy

Amazing experience! It was my first time on a sailing boat, and it was incredible. We visited beautiful places and beaches. Ale and Carlo are the perfect duo to sail with! Ale is professional, knows everything about sailing and the best beaches, and was always available and super friendly. Carlo was also very kind and helpful. I'm a vegetarian, and he always made something special just for me. Thank you for an unforgettable week! Hope to come back soon! :)
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/7/2025

Virginia B.

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Italy

Beautiful holiday, Andrea precise and very nice skipper made us discover wonderful places and entertained us. Another honorable mention to Marta who fed and pampered us. Mattias a real sea dog! You are missing already!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

Dario B.

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Italy

A great experience! It was not my first sailing cruise but certainly the most beautiful. Alessandro is young but competent, he knows the area and the seabed very well and, not least, he is kind and very helpful with everyone. Carlo is formidable, helpful, super sporty and cooks great! Together with his brother we created a small flotilla of two boats, and also a nice group. With them we saw the most beautiful places in the area. I was a bit skeptical about Corfu before leaving, but I had to change my mind, and from the boat it is a completely different perspective. 5 stars on everything, super deserved.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

francesco f.

What can I say.. First boat trip absolutely unforgettable. Thanks to Ale, the skipper, always attentive and available to our every need or request. Thanks to Carlo, an essential steward always with a smile on his face, as well as an excellent cook and great "suppista". And thank you both for the pleasant chats while browsing. An experience that we will certainly repeat with the same crew. Not if, but when... A greeting also to Eros, a short but intense company. See you soon!.

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