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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.

23

experiences

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5.0

Sailing WellEssere in Ionian Greece

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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7 travellers

Starting from

€1,215

€1,350

Per person

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4.3

In the Sea of Ulysses among the most beautiful islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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11 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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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

€285

€300

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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5.0

Corfù Paxos Antipaxos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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12 travellers

Starting from

€900

Per person

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4.3

By Catamaran between the islands of Poseidon and Corfu

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

Starting from

€750

Per person

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5.0

Corfu to Kefalonia

Duration:

7 days - 6 nights

Greece:

Ionian Islands

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4 travellers

€1,000

Per person

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Classical Greece by sailing catamaran

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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2 travellers

Starting from

€1,300

Per person

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5.0

Corfu, Albania and Diapontie Islands

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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12 travellers

€900

Per person

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4.8

Super!

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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72 travellers

Starting from

€722

Per person

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4.8

Wandering among the Ionian islands from Nydri to Preveza

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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2 travellers

€950

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

74 reviews

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

05/7/2025

Janette G.

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Australia

After sailing in the teeth of the Meltemi in the eastern Aegean 2 years ago Chris and I were happy to accept an invitation from friends to sail with Sail square in the gentle waters of the southern Corfu strait. Our hopes for a relaxing week on the water were fulfilled, largely due to the sailing skill and the care of Alessandro and his crew. We and our friends were comfortably accommodated in 2 cabins, each with a bathroom. All was clean and well-maintained. Our hostess, Marta, provided delicious Greek breakfasts and lunches. While sailing in the beautiful waters between Corfu, Paxos and Antipaxos, there were many opportunities for swimming at lovely beaches and walking in the islands. Alessandro and his crew, including the ship’s dogs, were exceptionally good hosts and we recommend this experience unreservedly. Lucy and Chris Costas May 2025
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

04/21/2025

Luna G.

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Belgium

We just had an amazing holiday! Alessandro and his brother Andrea made sure everything was perfect and truly unforgettable. Everything was well-organized and taken care of down to the smallest detail. They constantly checked if we needed anything and made us feel completely at ease. The food on board was absolutely delicious every single time. Thanks to them, it really felt like a dream vacation. Highly recommended!
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Gone with the Wind: Corfu and the Ionian Islands

04/1/2025

jenna C.

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Canada

I was so excited to go sailing in Greece. This dream unfortunately took a quick turn into a nightmare. The captain didn’t take us to any of the sites listed on the itinerary. We stayed close to the original port the whole trip. We would ask him each day to go to one of the listed places and he would just ignore the suggestions. He would also blame it each day on the weather yet we had beautiful weather the whole trip, minus the first day. The boat itself was constantly breaking down. We had a broke toilet which was not a plus. But the worst part of the trip was when the captain used the outside shower in front of myself and a few of the other girls on the boat. He proceeded to take his swim shorts off deliberately flashing his private parts to us. All the lady’s became super uncomfortable on the boat afterwards. It was super inappropriate. Would highly recommended spending your money elsewhere. Was a horrific experience.
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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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