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Sailboat yacht sailing holidays & tours in Greece

Discover more than 130 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

130

experiences

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From Paros to Milos, the hidden gems of Cyclades

Duration:

5 days - 5 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€765

€900

Per person

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Paros-Naxos and Small Cyclades

Duration:

5 days - 5 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€765

€900

Per person

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4.9

Super!

From Santorini to Milos: the fantastic Cyclades of the South

Duration:

7 days - 7 nights

Greece:

Cyclades

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2 travellers

€810

€900

Per person

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4.8

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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64 travellers

Starting from

€650

€722

Per person

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4.7

From Sicily to Greece crossing the Strait of Messina

Duration:

6 days - 7 nights

Greece:

Peloponnese

Give this experience a try!

€621

€690

Per person

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4.7

Great sailing from Athens to Mykonos in the Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€621

€690

Per person

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5.0

Super!

Corfu and the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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2 travellers

€711

€790

Per person

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5.0

7 islands in VIP formula - only 4 guests on board

Duration:

9 days - 9 nights

Greece:

Dodecanese

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3 travellers

Starting from

€1,215

€1,350

Per person

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4.7

Athens and the jewel islands of its gulf: Aegina, Poros, Idhra

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

€621

€690

Per person

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4.9

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€711

€790

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

€396

€440

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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4 travellers

Starting from

€1,215

€1,350

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

1610 reviews

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Gone with the Wind: Corfu and the Ionian Islands

04/1/2025

jenna C.

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Canada

I was so excited to go sailing in Greece. This dream unfortunately took a quick turn into a nightmare. The captain didn’t take us to any of the sites listed on the itinerary. We stayed close to the original port the whole trip. We would ask him each day to go to one of the listed places and he would just ignore the suggestions. He would also blame it each day on the weather yet we had beautiful weather the whole trip, minus the first day. The boat itself was constantly breaking down. We had a broke toilet which was not a plus. But the worst part of the trip was when the captain used the outside shower in front of myself and a few of the other girls on the boat. He proceeded to take his swim shorts off deliberately flashing his private parts to us. All the lady’s became super uncomfortable on the boat afterwards. It was super inappropriate. Would highly recommended spending your money elsewhere. Was a horrific experience.
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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 in the Cyclades

11/3/2024

Aaron S.

Amazing skipper, all the stops were fun the food was great and the overall atmosphere on the boat for the week was fantastic.
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Sailing cruise in the Greek islands - The Saronic Islands

11/3/2024

Stefano B.

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Italy

Grazie a Bertrand per avermi fatto fare una settimana memorabile in barca a vela , posti stupendi clima perfetto Grazie

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