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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.

27

experiences

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3.7

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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4 travellers

Starting from

€494

€549

Per person

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4.8

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

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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64 travellers

Starting from

€650

€722

Per person

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5.0

Super!

Corfu and the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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Alessandra M.

€711

€790

Per person

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5.0

Sailing WellEssere in Ionian Greece

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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6 travellers

€1,125

€1,250

Per person

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4.4

In the Sea of Ulysses among the most beautiful islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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4 travellers

Starting from

€675

€750

Per person

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4.9

Super!

Sailing Cruise in the Ionian Islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€665

€700

Per person

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4.8

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

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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4 travellers

€1,200

Per person

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4.4

Weekend a Corfù

Duration:

3 days - 3 nights

Greece:

Ionian Islands

Give this experience a try!

€390

Per person

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4.9

Super!

Easter in Corfu

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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2 travellers

€590

Per person

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YogaSail, Yoga Retreat on board a sailboat in the Ionian Islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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9 travellers

€850

Per person

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5.0

Corfù Paxos Antipaxos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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10 travellers

Starting from

€900

Per person

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4.8

Catamaran with Chef in the magical sea of the Ionian Islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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43 travellers

Starting from

€1,150

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

71 reviews

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

03/23/2025

Matt V.

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United States

Absolutely phenomenal sailing adventure with Alessandro and Andrea! From the moment we stepped aboard in Corfu with our three children (ages 7, 10 and 12), we knew we were in expert hands. They crafted the perfect itinerary, taking us to the stunning islands of Paxos and beyond, revealing the hidden gems of Greece. Our days were filled with unforgettable experiences: hiking to ancient temples, swimming and snorkeling in pristine bays, collecting sea shells, exploring historic castles, and wandering through charming seaside towns. The boat was incredibly comfortable, making our nights as enjoyable as our days. The meals onboard were all excellent as well and the accomodations were clean and cozy. Alessandro and Andrea's hospitality was truly exceptional. They are not only skilled sailors, but also passionate guides, sharing their love for Greece with us. They even played Uno with our kids every afternoon. Their knowledge and enthusiasm made this vacation one of the best we've ever had. Thank you, Alessandro and Andrea, for showing us the most beautiful side of Greece! You are simply the best! 5 stars without a doubt.
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The alternative to the catamaran in the Ionian Islands

10/15/2024

Belinda B.

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Australia

Best live aboard sailing trip I have done. The boat was exceptionally comfortable and everything clean and in ship shape ! The skipper was great at helping us learn the ropes to participate in the sailing if we wanted to. I loved having the SUP and snorkel sets on board to use when we moored in beautiful bays. It was terrific to catch fresh fish to eat along the way too. Thanks so much to Manuele for making my first trip to Greek Is such a wonderful experience.
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

10/7/2024

Lorenza G.

La barca è molto accogliente e ben tenuta. Lo skipper molto competente, disponibile e rassicurante. Abbiamo navigato a vela e fatto bellissimi bagni nonostante il meteo non sia stato dei migliori. Esperienza da consigliare.
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

10/4/2024

Francesca S.

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Italy

Ottima esperienza, belle isole ed un capitano davvero molto bravo, sempre disponibile, attento e molto competente, anche a schivare i nuvoloni che in quel periodo agitavano cielo e mare. Bella barca e comoda.

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