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Private yacht sailing holidays with skipper in the Ionian Islands

Who has never dreamed of hiring a sailboat and following Ulysses' routes? In the Ionian Islands you can choose between a sailboat, a catamaran or a gulet and sail to Zante, Ithaca, Corfu, Lefkada, Kastos.

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - October

Starting from

€550

Per person

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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

3 departures available

August - October

Starting from

€550

Per person

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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

One departure available

September

€900

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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5.0

Super!

Lose yourself in the magic of the Southern Ionian Islands

Greece: Ionian Islands

7 days - 6 nights

One departure available

August

€1,000

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

3 departures available

August - September

Starting from

€600

€540

Per person

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4.8

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€1,150

Per person

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4.8

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,200

Per person

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4.1

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Greece: Ionian Islands

6 days - 6 nights

One departure available

August

€549

Per person

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5.0

Classical Greece by sailing catamaran

Greece: Ionian Islands

7 days - 7 nights

One departure available

August - September

€1,300

Per person

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4.3

Gone with the Wind, Corfu and the Poseidon Islands

Greece: Ionian Islands

6 days - 7 nights

One departure available

September

€595

Per person

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Ulysses' routes

Greece: Ionian Islands

7 days - 7 nights

One departure available

August - September

€1,200

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 - Private yacht sailing holidays with skipper in the Ionian Islands

114 reviews

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

08/20/2025

Gaia C.

-

Italy

First experience on a sailing boat for us and we are very happy to have had it with Alessandro and Carlo. Alessandro is prepared, helpful and an extremely kind person. The places chosen for the tour and the organization in general made us feel always in excellent hands. Carlo's presence is a plus for sympathy and professionalism!
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Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

08/20/2025

Yamin Y.

-

Italy

We had an unforgettable week sailing with Arthur, an adventure we’ll always remember. We shared moments of life, duties on board, and learned a lot about sailing. Arthur is a very knowledgeable skipper and guided us skillfully, adapting each day to the winds and leading us to hidden coves and peaceful spots far from the crowds. Arthur is friendly, easygoing and willing to share his knowledge. Dice games and interesting chats at night are a nice plus. The boat has a lot of character: you can feel it has a history and a life of its own, which makes the journey authentic and special. The common spaces are not very large, but cozy and livable, perfect if you’re looking for a true sailing adventure and it was exactly what made the week so unique and real. This was not just a holiday, it was a journey of freedom, learning, connection, and discovery. We couldn’t have asked for a better skipper or a better adventure. Highly recommended!
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Catamaran ride in the sea of Ulysses

08/18/2025

Javier Y.

-

Spain

Leo great captain and person
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Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

08/17/2025

Vincenzo P.

-

Italy

Arthur Excellent Skipper, always ready to solve unforeseen events that are never lacking on the boat, connoisseur of all the most beautiful coves and places on land to visit. During the days there are several stops in various places making every day never boring. PLUS evening group games on the boat.

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