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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

96

experiences

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Antiparos Discovery Schooner Tour - Despotiko - Blue Lagoon

Duration:

1 day - 0 nights

Greece:

Cyclades

Give this experience a try!

€130

Per person

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7 Day Greek Sailing Adventure - Dodecanese Islands

Duration:

7 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€1,653

Per person

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The sailing adventure of your summer - Steward on board

Duration:

7 days - 6 nights

Greece:

Dodecanese

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+2 travellers

have booked

€1,450

Per person

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4.6

Cruise to the Ionian Islands, Ithaca and Zakynthos on a luxury boat with chef

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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+24 travellers

have booked

€1,200

Per person

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4.6

A complete cruise, real sailing, quiet bays and relaxation

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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+2 travellers

have booked

€750

Per person

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4.9

Cyclades and Microcyclades with a magnificent 15-meter boat

Duration:

7 days - 7 nights

Greece:

Cyclades

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+24 travellers

have booked

Starting from

€750

Per person

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5.0

The enchantment of the sea: the Dodecanese islands

Duration:

7 days - 7 nights

Greece:

Dodecanese

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+10 travellers

have booked

Starting from

€650

Per person

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5.0

Ionian Islands by sailboat

Duration:

7 days - 6 nights

Greece:

Ionian Islands

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+3 travellers

have booked

Starting from

€900

Per person

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4.8

In the sea of Ulysses among the most beautiful islands - two boats together

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+8 travellers

have booked

Starting from

€570

Per person

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4.8

Gone with the Wind, in the sea of Ulysses among the most beautiful islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+25 travellers

have booked

Starting from

€570

Per person

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5.0

Corfu, Albania and Diapontie Islands

Duration:

6 days - 5 nights

Greece:

Ionian Islands

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+2 travellers

have booked

Starting from

€850

Per person

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5.0

Sailing Cruise in the Greek Islands - The Ionian Islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

Starting from

€800

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 - Yacht sailing holidays & skippered tours in Greece

1549 reviews

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Da Zante a Milos attorno al Peloponneso, un itinerario incontaminato

06/12/2024

Flavia I.

-

Spain

It was a great experience sailing with Andreas. A life memory. I travelled with a friend and a five years old kid, he was very careful about my daughter, made her feel secure and confident too. The boat is great for a big group, with enough space for everyone and also for some privacy. Peloponeso is a destination for those looking for quiet landscapes, natural and cultural history, little tourism and plenty of sailing, from 4 to 9 hours the longest trail. You dive deeply and softly into Greece. I would much recommend it, we will for sure. Hugs Andreas, your are the best Capitano!
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The fantastic Saronic Islands and the surroundings of Athens

06/5/2024

Anja W.

-

Mexico

I recently returned from a one-week sailing trip to the Saronic Islands it was an absolutely fantastic experience. This was my first time on a sailing boat and I couldn't be happier with how everything turned out. Alessandro, our very knowledgeable and experienced skipper, was the best I could have wished for. He made me feel very safe throughout the journey and ensured the entire experience was super relaxed. We visited many stunning islands, each with its own charm. Allessandro took us to beautiful, quiet bays for swims, away from the crowds, making each stop feel like a private paradise. He also knew all the best restaurants, where we enjoyed delicious local cuisine. The boat itself was beautiful and very comfortable, providing the perfect home away from home. This trip was everything I hoped for and more. I highly recommend this sailing adventure and can't wait for my next trip!
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Da Zante a Milos attorno al Peloponneso, un itinerario incontaminato

06/2/2024

Fernando S.

-

Paraguay

Agradecimiento eterno al Capitán Andrea y a su Velero Neverlan. Las locaciones, los momentos y los aprendizajes fueron Inmensos como el Peloponeso! Esta experiencia, llena, cura, divierte, sorprende y engorda al Alma! Gracias por tanto querido Capitán!
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The fantastic Saronic Islands and the surroundings of Athens

05/21/2024

Steve T.

-

Canada

My family and I spent a week onboard with Alessandro exploring the Saronic Islands. We were taken to some amazing places that I will remember forever. Some were busy with people and tourists and some were completely ours - just the bay and our boat. This was a trip of a lifetime with a great skipper!

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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

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