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Sailboat yacht sailing holidays & tours in Ionian Islands

Discover more than 10 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

4 departures available

October

€570

Per person

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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

September - October

Starting from

€570

Per person

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5.0

Super!

The enchantment of the sea: Lefkada, Ithaca, Kefalonia and the smaller islands

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€600

Per person

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New

Premium

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,645

Per person

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4.7

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

€600

€540

Per person

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4.4

Premium

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

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5.0

Discovering the Northern Ionian Islands

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

€1,000

Per person

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5.0

New

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

Greece: Ionian Islands

6 days - 6 nights

6 departures available

September - October

Starting from

€1,200

€500

Per person

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4.4

Gone with the Wind, Corfu and the Poseidon Islands

Greece: Ionian Islands

6 days - 7 nights

One departure available

September

€630

Per person

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5.0

Exclusive sailing week among the wonders of Ionian Greece

Greece: Ionian Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€1,200

Per person

Why book a holiday with Sailsquare?

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Reviews - Sailboat yacht sailing holidays & tours in Ionian Islands

971 reviews

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

09/15/2026

AnnMarie S.

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US

Amazing vacation! I would compare it to somewhere between camping and glamping, but on the sea! We saw the most beautiful beaches, sunsets, and sunrises. We sailed along side dolphins, explored caves, and even saw sea urchins and octopus when we were snorkeling. Caroline was our chef an overall caretaker. She catered to our every need and the best meals we had all week were the breakfasts and lunches that she cooked for us! The boat fits up to six guests. Two of the three rooms are extremely small so if you go with friends, you will be sleeping in the same bed since there is only one bed per room. There is also no indoor shower. You shower in your bathing suit out in the open on the back of the boat. I would highly recommend privatizing the boat if you go with a group of friends. We thought we had done so, but then we found out at the last minute that there was miscommunication and a man was joining us four girls. He was very nice, but we would’ve preferred to only have one girl per small room versus doubling up and having to share space/a bathroom with a man. Overall it was a fabulous experience and I would most definitely do it again!

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

09/14/2026

Elizabeth B.

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AR

Spectacular week, Alessandro super friendly, courteous, organized and fun. He took us to amazing places. Carlo: wonderful person, excellent cook and always available with his smile and unique warmth. The group climate on board was optimal. Unbeatable week!!!!

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

09/14/2026

Giuseppe L.

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IT

I had a fantastic and totally relaxing week on the boat with Andrea and Carol. Thanks to the skipper's experience and deep knowledge of the area, we discovered unique and wonderful beaches. Andrea never leaves anything to chance and knows how to make you feel at home at all times. Carol is an exquisite person, always kind, attentive to every little need and an excellent cook. A memorable experience that I recommend to everyone!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/13/2026

Carolina V.

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US

We had the most incredible experience with Sailing with Andrea. He made us feel safe from day one while still keeping things fun and full of energy. You could tell right away how professional and experienced he is on the water. He took us to the most beautiful spots around Paxos, Anti Paxos, and Corfu, places we never would have found on our own. While other tours crowd into the same touristy spots, Andrea took us to the most secluded, hidden gems along the coast! Caroline, our hostess, was just as wonderful. She was warm, attentive to every detail, and her cooking was fantastic, every meal felt like a treat. Between the two of them, we felt like we were staying at a 1000-star hotel! We had a hilarious volleyball match in the shallow water, our boat against another, one of the most fun moments of the whole trip! If you're looking for a trip that combines beautiful places and genuinely lovely people taking care of you, this is it. We can't wait to sail with them again!

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