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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!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

5 departures available

May - October

Starting from

€950

€855

Per person

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4.8

Super!

Catamaran with Chef in the magical sea of the Ionian Islands - Holiday for SINGLES

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,450

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€890

Per person

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5.0

Super!

From Santorini to Milos by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

July - August

€1,050

Per person

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Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

6 departures available

May - October

Starting from

€779

€701

Per person

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

Greece: Ionian Islands

7 days - 7 nights

6 departures available

July - October

Starting from

€779

€701

Per person

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4.6

From Athens to Evia and Skiathos,: the Sporades on a yacht with chef - One Way

Greece: Sporades

7 days - 7 nights

One departure available

May

€950

Per person

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4.4

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

17 departures available

May - October

Starting from

€1,525

€1,373

Per person - min 2 pax

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4.4

Premium

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

Greece: Ionian Islands

7 days - 7 nights

13 departures available

June - October

Starting from

€845

€761

Per person - min 2 pax

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5.0

Sailing BenEssere in Ionian Greece

Greece: Ionian Islands

7 days - 7 nights

3 departures available

June - August

€1,250

Per person

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4.6

Discover the most authentic Greece from Samos to Arki and Agathonisi, with skipper and chef

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€1,200

€1,080

Per person

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Aegean dreams: sailing around Rhodes - hostess on board (half board)

Greece: Dodecanese

7 days - 7 nights

10 departures available

July - October

Starting from

€829

€746

Per person

Why book a holiday with Sailsquare?

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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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

251 reviews

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

05/11/2026

Lucia K.

-

Switzerland

Our sailing holidays around Corfu were simply exceptional. The combination of crystal-clear waters, stunning islands, and peaceful hidden bays made every single day unforgettable. The crew Andrea, Marta & Mattias was incredibly friendly, professional, and always made us feel welcome and relaxed on board. The itinerary was perfectly balanced between discovering beautiful Greek islands, enjoying time at sea, and experiencing authentic local culture. The food was another highlight — fresh, delicious, and healthy, with plenty of local specialties prepared with care. It was truly a unique and unforgettable experience that we would highly recommend to anyone looking for the perfect mix of adventure, relaxation, and comfort.
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/22/2025

Douglas B.

-

United Kingdom

An extraordinary experience that exceeded all expectations

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

10/19/2025

Catherine S.

My first sailing experience was simply extraordinary! ⛵️ Unforgettable moments spent at sea, surrounded by incredible people. Anna Lisa and Emmanuel were amazing hosts! Thank you to everyone for your good humor, your kindness and this unique adventure. Can't wait to do it again! 🌊✨
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/19/2025

Olivier P.

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France

Some sailings leave a softer trace than that of the boat's wake. The sailing week was perfect: beautiful sailing, delicious food and a friendly atmosphere. Thank you to them for this wonderful interlude — I will leave without hesitation!

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