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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.

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4.6

From Kos to Rhodes on my catamaran

Greece: Dodecanese

7 days - 7 nights

One departure available

August - September

€980

Per person

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4.8

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€1,150

€950

Per person

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€1,260

Per person - min 2 pax

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4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€2,100

€1,995

Per person

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4.8

Magical Week of Wellness Yoga, Cooking, Health, and Relaxation

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,200

Per person

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5.0

Classical Greece by sailing catamaran

Greece: Ionian Islands

7 days - 7 nights

One departure available

August - September

€1,300

Per person

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Discovering the real Greece by catamaran - Southern Ionian and the calm of September

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,250

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

5 days - 6 nights

One departure available

September

€1,995

Per person

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4.6

From Sifnos to Corinth, from the Cyclades to Saronic

Greece: Cyclades

6 days - 7 nights

One departure available

September - October

€750

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 - Catamaran yacht sailing holidays & tours in Greece

108 reviews

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Catamaran ride in the sea of Ulysses

08/18/2025

Javier Y.

-

Spain

Leo great captain and person
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/18/2025

Francesco P.

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Italy

Amazing adventure holidaying across the most beautiful seas Aga & Greg loving and caring hosts Incredible local vegetarian and healthy food experience on board And tavern selection for the nights on the ground A must try experience!
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/17/2025

Maxime M.

-

Italy

What a wonderful week with Aga, Greg and the other travellers. Magnificent landscapes of course but also and above all a great crew who made us discover the less touristy places, delighted us with an exceptional cuisine and the boat is beautiful and very comfortable. Only positive. We will be back for sure!
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/8/2025

Vivian M.

-

United States

The boat and the scenery are great, and Aga’s food is simply the most amazing fresh food I’ve ever eaten in my whole life. I’m not giving five stars for two reasons: first, the advertisement mentioned air conditioning, but most nights I felt really hot, as the AC was only turned on for one hour on one night during my trip. Second, at times it felt a bit like a military camp, with the captain being quite impolite with no excuse.

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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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