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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!

149

experiences

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3.2

2 catamarans to discover the Central Cyclades and Micro Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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6 travellers

Starting from

€890

€1,113

Per person

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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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3.7

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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4 travellers

Starting from

€494

€549

Per person

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4.7

From Santorini to Rhodes: sailing through fairytale scenery

Duration:

6 days - 7 nights

Greece:

Dodecanese

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4 travellers

€648

€720

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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Alessandra M.

€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

Give this experience a try!

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

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

1734 reviews

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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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Sailing cruise in the Greek islands - The Saronic Islands

11/2/2024

Elie R.

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France

Super semaine ! Bertrand est expert de la région et nous a emmenés à des endroits magnifiques en s'adaptant aux conditions météo et aux capacités et envies de l'équipage. Le bateau est très confortable, il y a même l'eau chaude ! Merci captain Jack et à une prochaine on espère !

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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

Greece: departures by month

Other travel ideas

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