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Sailboat yacht sailing holidays & tours in Greece

Discover more than 112 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

112

experiences

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5.0

Super!

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

Duration:

7 days - 6 nights

Greece:

Dodecanese

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6 travellers

€950

Per person

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5.0

Super!

Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

Duration:

7 days - 6 nights

Greece:

Cyclades

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4 travellers

€740

Per person

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SAILING & IDLENESS Argo-Saronic Gulf

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

€1,960

Per person

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5.0

Super!

The enchantment of the sea: the Dodecanese islands

Duration:

7 days - 7 nights

Greece:

Dodecanese

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45 travellers

€650

Per person

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5.0

Super!

From the Dodecanese to the Cyclades: sailing off the beaten track!

Duration:

10 days - 10 nights

Greece:

Dodecanese

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7 travellers

€800

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Duration:

6 days - 7 nights

Greece:

Cyclades

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6 travellers

€835

Per person

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4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

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23 travellers

€800

Per person

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4.7

Premium

One way Aegina - Naxos sailing adventure on a big 50ft boat

Duration:

6 days - 7 nights

Greece:

Cyclades

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4 travellers

€1,100

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Santorini to Kos

Duration:

7 days - 6 nights

Greece:

Cyclades

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11 travellers

€1,050

Per person

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4.9

A week in the flotilla in the Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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14 travellers

€1,050

Per person

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4.9

From Paros to Athens, sailing between the Cyclades and the Saronic Gulf

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€750

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

€1,300

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 - Sailboat yacht sailing holidays & tours in Greece

1615 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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