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Crewed yacht sailing holidays & tours in Greece

Get on board on a crewed sailing holiday in Greece for the most relaxed time ever.

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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

3 departures available

September - October

Starting from

€550

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

€790

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.7

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

6 departures available

September - October

Starting from

€1,100

€1,045

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

2 departures available

September - October

Starting from

€550

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

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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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€1,260

Per person - min 2 pax

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4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€2,100

€1,995

Per person

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4.6

The Cyclades with Serifos and Mykonos on a dream boat with chef

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,400

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

One departure available

September

€1,150

€950

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 - Crewed yacht sailing holidays & tours in Greece

228 reviews

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ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

08/31/2025

Marianna C.

-

Italy

The islands are not great, Hydra and Spetzes are the only nice ones. The skipper was definitely unpleasant, he always took us to the ports immediately after lunch and the moorings in the bays were always almost offshore. Fortunately I had my sup to get closer but other older passengers found themselves in difficulty. He was also always nervous and responded very rudely. I was asked for a supplement for gluten and lactose free food of € 240 and for the first two days I was not given any substitute food, things were simply removed. Only after reporting the matter to sailsquare and the hostess did she organize herself a little better. I don't think I will repeat the experience with this group unfortunately.
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/31/2025

Michele L.

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Portugal

Amazing adventure. Aga, Aja and Greg are supportive and dedicated. Notwithstanding the weather conditions have been challenging for sailing beginners they managed to make our trip amazing. Aga and Aja’s breakfasts and lunchs are healthy, tasty and creative!
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Fast cruising Cicladi Occidentali

08/26/2025

Sergio B.

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Italy

Annalisa and Lorenzo are first and foremost two wonderful people. Then they are two very experienced sailors: they have sailed around the world; they know the waters of the Aegean by heart. Finally, they are also great as cooks: where do you find the barbecue on the boat and the freshly hand-pulled egg pasta below deck? Only from them! The bays where they took us were breathtaking.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

08/25/2025

Laura C.

-

Italy

Beautiful week

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