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Yacht sailing holidays & skippered tours in Greece

Discover more than 25 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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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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4.4

Premium

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

Starting from

€845

€676

Per person - min 2 pax

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All inclusive catamaran cruise on a Bali 4.2 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€2,060

Per person

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4.7

Luxury catamaran cruises in the Greek islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

October - November

€1,000

Per person

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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€700

€665

Per person

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4.2

Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

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4.2

Where the blue feels like home: the Ionian islands - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

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4.2

Sailing the Aegean: a Greek Islands escape - hostess on board (half board)

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

Starting from

€929

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

4 departures available

October

Starting from

€1,200

€500

Per person

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4.7

Greek Islands Catamaran Cruise - Saronic

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

October

Starting from

€820

Per person

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All inclusive catamaran cruise on Excess 11 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,875

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

October

Starting from

€950

Per person

Why book a holiday with Sailsquare?

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Get onboard solo, with your family or your friends

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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 - Yacht sailing holidays & skippered tours in Greece

2122 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!
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Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

09/14/2026

Evi (Paraskevi) P.

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GR

[hidden] is a wonderful classy and spacious boat very well maintained so makes you feel safe and i couldn't get enough of the sunbathing on the lounge mattress on the bow of the boat. Captain Alessio is a down to earth,kind and calm person making this an Ideal combination for enjoying some relaxing holidays. Plus he has a lot's of knowledge around various subjects so it's really enjoyable talking to him. He made sure ,during our whole week in the Argosaronic gulf, to find for us the best anchorage with crystal clear waters. As i was the only person on board not speaking Italian captain Alessio and the rest of the crew never left me outside a conversation and always either translating or communicating in English.. Had a fantastic relaxing time, the chance to discover some sight seeing on the area make new friends and explore the local food culture. Thank You Captain.
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Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

09/14/2026

Lorenzo G.

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GB

A really enjoyable sailing holiday and a great way to discover the Saronic Islands. The trip offered a good mix of sailing, relaxing, and visiting interesting places, including destinations with plenty of cultural and historical interest. The boat was very well maintained and well equipped, so life on board was comfortable and easy. We had good food, good company and a very pleasant atmosphere throughout the trip. There were also plenty of opportunities to get involved in the sailing, which I particularly enjoyed. The skipper was friendly, easy-going, and always helpful, which made the whole experience very enjoyable. A very good holiday overall, and one I would happily recommend.

From Skiathos to Athens

09/14/2026

Elizabeth B.

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AR

Beautiful week of sailing. Fantastic places

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