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Catamaran yacht sailing holidays & tours in Greece

The Greek isles and their vast amount of coastline - of more than 16,000km is home to some of the world’s most beautiful islands and beaches. Embark on a beautiful sailing adventure aboard a spacious, comfortable catamaran.

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 - Catamaran yacht sailing holidays & tours in Greece

114 reviews

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From Kos to Rhodes on my catamaran

09/13/2025

Danielle O.

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Germany

Our first tour. We therefore have no comparison options yet and give a benevolent 4 stars. I would have liked better communication, more involvement and more sailing.
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2 Catamarans in Greece: discover the Sporades Islands with us

09/1/2025

Elisabetta A.

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Italy

Wonderful experience and above expectations! The skipper Fabrizio, in addition to being very experienced, perfectly interpreted the group's wishes by taking us every day to coves with spectacular water and different but intact and wild locations (including a natural park where everyone left their hearts), and alternating in a balanced way the much-loved roadsteads with stops in the ports, in which there was no lack of chore characteristics. We ate very well because in the lucky group there were very good chefs who prepared pasta, flatbread, fish and other delicacies every day! The boat was comfortable and organized! An experience for which I would leave today and that I recommend to all lovers of the sea experienced on a boat!
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2 Catamarans in Greece: discover the Sporades Islands with us

09/1/2025

Gabriella L.

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Italy

Beautiful holiday! Beautiful bays, wonderful colors, nice and close-knit travel companions, new and precious friendships, excellent skipper.. Gabriella.
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ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

08/31/2025

Marianna C.

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Italy

The islands are not great, Hydra and Spetzes are the only nice ones. The skipper was definitely unpleasant, he always took us to the ports immediately after lunch and the moorings in the bays were always almost offshore. Fortunately I had my sup to get closer but other older passengers found themselves in difficulty. He was also always nervous and responded very rudely. I was asked for a supplement for gluten and lactose free food of € 240 and for the first two days I was not given any substitute food, things were simply removed. Only after reporting the matter to sailsquare and the hostess did she organize herself a little better. I don't think I will repeat the experience with this group unfortunately.

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6 reasons to explore Greece on a catamaran for your next sailing holiday:

  • Discover some of the world’s most beautiful coves and lagoons in the comfort of a catamaran.
  • Explore the thousands of Greek islands aboard a catamaran with a weak draft, allowing them to venture into shallower waters than a monohull - meaning you can travel with an unrivalled level of freedom!
  • Board a spacious catamaran, that allows a most comfortable sailing experience possible - especially when travelling as a family or a larger group!
  • As a catamaran has less movement at sea than a monohull sailboat, it is perfect for first time sailors, reducing any concerns about sea sickness.
  • Experience all of the treasures of Greece - including the famous isles of Santorini, Mykonos, and Ios as well as the native sirtaki dance of the street festivals.
  • Immerse yourself into the beautiful atmosphere and charming architecture of Greece’s coastal regions aboard a catamaran.

The best destinations to visit on your holiday to Greece aboard a catamaran:

Famous sailing areas include the Cyclades, the Saronic islands, Ionian islands, Dodecanese, Sporades, and Crete - however, there are an estimated 5,000-6,000 islands in Greece. Corfu, Mykonos, and Santorini are some specific destinations that are particularly magical to explore by a sailing holiday.

Travelling the Greek isles by sailboat allows for full exploration of the areas treasures, that would otherwise be inaccessible. This is even more so the case when travelling by catamaran, due to the weak draft of the boat, meaning shallow waters inaccessible to many monohull boats can be explored! Whether you are planning to travel solo, as a couple, with friends or family, and whether you are looking for a sailboat or catamaran experience, there are numerous areas of Greece that make for perfect holidaying destinations. Learn more about sailing in Greece.

Tips to help you to better plan for your next sailing holidays in Greece aboard a catamaran:

When to visit Greece & transport options

Temperatures and the climate in Greece are pleasant and generally good for sailing from April through to November. Due to the fact that July and August are more popular for holidaying, if possible, it is worth considering travelling during May, June, September, or October if you would prefer a quieter, slightly more tranquil holiday.

Greece is home to a number of international airports such as Athens, Corfu, Kos, and Kefalonia. Greece has a well developed system of ferries that transport travellers from island to island. The organising skipper of any given trip will be able to give you the most relevant information about transport routes to and from your points of embarkment and disembarkment.

Sailing with a family aboard a catamaran with a local skipper

There are some sailing regions that are better suited and equipped for family sailing trips, and Greece is one of these regions. There is a good mix of modern marinas and harbouring options as well as more secluded bays and coves for you to enjoy with your family. All forms of sailing holiday with family holidays included, benefit greatly from having an experience local skipper leading the trip. Travelling with a skipper with such insider knowledge allows you to fully immerse yourself in the enjoyment, relaxation, and adventure of the sailing holiday in the Greek isles.

Greece: the best travel ideas

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