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Yacht sailing holidays & skippered tours in Greece

Discover more than 52 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

52

experiences

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5.0

Sailing Yoga and SUP trip in the SARONIC ISLANDS Greece

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

Starting from

€990

Per person

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4.3

Gone with the Wind, Corfu and the Poseidon Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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2 travellers

€595

Per person

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4.9

Super!

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

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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102 travellers

Starting from

€530

Per person

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4.6

The Sporades of "Mamma Mia": holiday with skipper and hostess

Duration:

7 days - 7 nights

Greece:

Sporades

Give this experience a try!

€1,300

Per person

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5.0

Super!

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

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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107 travellers

Starting from

€530

Per person

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4.6

From the Gulf of Corinth to the Sporades on my catamaran

Duration:

7 days - 7 nights

Greece:

North Egean Islands

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4 travellers

€750

Per person

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4.3

Gone with the wind, discovering the Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€690

Per person

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5.0

Exclusive sailing week among the wonders of Ionian Greece

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

Starting from

€1,300

Per person

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3.3

Sailing to Corfu

Duration:

7 days - 7 nights

Greece:

Ionian Islands

Starting from

€732

Per person

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5.0

Super!

Sailing in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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242 travellers

Starting from

€1,080

Per person

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5.0

Sail the Greek Islands with Skipper & Hostess

Duration:

6 days - 6 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

Starting from

€1,265

Per person

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4.9

Super!

Sailing cruise in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€750

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 - Yacht sailing holidays & skippered tours in Greece

1740 reviews

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Sailing cruise in the Greek islands - The Saronic Islands

05/12/2025

Monika L.

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Germany

Skipper Bertrand machte einen super Job! Wir sind unerfahrene Segler und fühlten uns absolut sicher und sehr gut aufgehoben. Auf die mehrtägige Flaute (und seine sehr unterschiedlichen Gäste an Bord) hat Bertrand total flexibel und entspannt reagiert. Mach bitte weiter so! Auch die Orga mit sailsquare war perfekt- wir sind glücklich und sehr zufrieden von Bord gegangen und empfehlen Euch gern weiter!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

05/7/2025

Janette G.

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Australia

After sailing in the teeth of the Meltemi in the eastern Aegean 2 years ago Chris and I were happy to accept an invitation from friends to sail with Sail square in the gentle waters of the southern Corfu strait. Our hopes for a relaxing week on the water were fulfilled, largely due to the sailing skill and the care of Alessandro and his crew. We and our friends were comfortably accommodated in 2 cabins, each with a bathroom. All was clean and well-maintained. Our hostess, Marta, provided delicious Greek breakfasts and lunches. While sailing in the beautiful waters between Corfu, Paxos and Antipaxos, there were many opportunities for swimming at lovely beaches and walking in the islands. Alessandro and his crew, including the ship’s dogs, were exceptionally good hosts and we recommend this experience unreservedly. Lucy and Chris Costas May 2025
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Sailing cruise in the Greek islands - The Saronic Islands

05/4/2025

Riccardo P.

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Italy

La barca è curata ed in ottime condizioni. Bertrand è premuroso, affidabile e sempre disponibile. Le isole Saroniche sono state una bellissima scoperta e meritano sicuramente di essere visitate. Una settimana fantastica!
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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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