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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.

46

experiences

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5.0

Super!

Corfu and the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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3 travellers

Starting from

€711

€790

Per person

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5.0

Sailing WellEssere in Ionian Greece

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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6 travellers

Starting from

€1,215

€1,350

Per person

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4.7

Premium

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

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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45 travellers

Starting from

€1,995

€2,100

Per person

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4.7

Premium

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

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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135 travellers

Starting from

€998

€1,050

Per person

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4.6

Sailing in the most beautiful Saronic with chefs: Hydra and Spetses

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

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2 travellers

Starting from

€1,235

€1,300

Per person

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4.7

Premium

Sporades one way on a big and comfortable 60ft catamaran with chef

Duration:

5 days - 6 nights

Greece:

Sporades

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2 travellers

€1,898

€1,998

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Duration:

6 days - 7 nights

Greece:

Cyclades

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47 travellers

Starting from

€2,185

€2,300

Per person

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4.9

Super!

Corfu to Athens via the exciting Corinth Canal

Duration:

8 days - 8 nights

Greece:

Saronic Islands and Athens area

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4 travellers

€418

€440

Per person

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4.9

Super!

Cyclades on a sailing boat: adventure with comfort!

Duration:

7 days - 7 nights

Greece:

Cyclades

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6 travellers

€665

€700

Per person

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4.6

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

Duration:

7 days - 7 nights

Greece:

Sporades

Give this experience a try!

€1,150

Per person

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4.4

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

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8 travellers

Starting from

€1,260

Per person - min 2 pax

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4.9

Super!

Sailing and Relaxation Educational Course

Duration:

11 days - 11 nights

Greece:

Peloponnese

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5 travellers

€1,000

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 - Crewed yacht sailing holidays & tours in Greece

178 reviews

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

10/30/2024

Santiago D.

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Colombia

A unique and spectacular experience! I sailed for a week and I loved it! Highlights: we sailed every day, the breakfast and lunches were incredible (we all asked for the recipes) and at night we went out to eat at typical restaurants on the Greek islands. I hope to return soon!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/20/2024

Hollie D.

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Australia

Alessandro made us feel seen and safe. He is quiet knowledgeable and did his best to try ensure we were all happy. Recommend

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