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Catamaran yacht sailing holidays & skippered tours

Discover the magic of skippered catamaran holidays, an original holiday idea to share a comfortable adventure with family or friends in a little bit of luxury. Catamaran holidays in the Caribbean including the Grenadines, Seychelles, Martinique, Antigua and Barbuda, and Cuba - as well as in the Mediterranean including Greece, Croatia, Corsica, and Sardinia. The world’s best travel destinations await you.

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4.8

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - October

Starting from

€950

Per person

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5.0

Super!

Week on the Costa Smeralda on a full optional catamaran!

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

July - August

Starting from

€1,150

Per person

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4.7

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

8 departures available

August - November

Starting from

€1,455

€1,382

Per person

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4.5

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

6 departures available

July - September

Starting from

€1,040

€936

Per person

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5.0

Super!

Kornati Islands: a week on a catamaran among the pearls of Croatia

Croatia: Kornati Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€1,400

Per person

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4.8

Super!

Egadi Islands by catamaran with stewardess and cook on board

Italy: Aegadian islands

7 days - 7 nights

2 departures available

July

Starting from

€1,200

€1,080

Per person

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5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

4 departures available

July - August

Starting from

€1,100

€935

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Greece: Cyclades

6 days - 7 nights

One departure available

August

€2,947

€2,800

Per person

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4.9

Unforgettable Catamaran Cruise in Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

2 departures available

August

Starting from

€1,243

Per person

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4.9

Super!

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€870

Per person

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4.8

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

7 days - 7 nights

One departure available

August - September

€1,300

Per person

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4.9

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Italy: Aeolian Islands

7 days - 7 nights

One departure available

July - August

€2,625

€1,940

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 - Catamaran yacht sailing holidays & skippered tours

1036 reviews

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

07/5/2025

Gill B.

-

United Kingdom

One of our best holidays ever! Beautifully kept boat, beautiful food, beautiful people to be with for a week… would definitely book again !
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North Sardinia and South Corsica by catamaran with flybridge

07/1/2025

Mark S.

-

Germany

Incredible vacation!
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Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

06/30/2025

Beatrice S.

-

Spain

No se podía esperar más de un viaje. El catamarán grande y nuevo. A/C siempre que hacía falta y agua en abundancia. El Capitán Lutius no podía ser más profesional y simpático. Nos hizo sentir a todos cómodos y siempre proponiendo hacer diferentes actividades en un ambiente divertido y desenfadado. Karin, la chef igualmente agradable y divertida. Muy profesional y atenta a nuestras necesidades. Los lugares que visitamos de ensueño y a pesar de algunas lluvias en línea general ha merecido la pena navegar fuera de temporada al estar prácticamente solos en los sitios más alucinantes. Siempre hemos tenido suerte con el resto de los clientes y en este caso no ha sido diferente y a pesar de ser mayoritariamente de habla francesa nos hemos comunicado muy bien en inglés.
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Elba and the Tuscan archipelago on board a catamaran

06/30/2025

Stefania B.

-

Italy

Come prima esperienza di vacanza in barca da sola posso dire che è andata alla grande. Grazie a un tempo favorevole abbiamo raggiunto la Corsica (fantastica) e vissuto tutta la settimana in barca, senza mettere mai piede a terra: quello che volevo. Barca comodissima con spazio per tutti ! Pranzi e cene stellati (in tutti i sensi). Il capitano [hidden] esperto e disponibile, ha condiviso ogni decisione con il gruppo . Cris, suo fidato braccio destro, sempre operativo e paziente a tutte le varie nostre richieste. Esperienza che consiglio vivamente. TORNERÒ SICURAMENTE

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7 reasons to go on a sailing holiday on a catamaran with a skipper

  • A catamaran is described by many as a floating house: comfortable, spacious, bright, and very well equipped.
  • Ideal for families with children, with room and the environment that is more secure than a monohull sailboat.
  • A new way of travelling that allows you to discover islands and paradisiacal beaches that are only accessible by boat - the catamaran has a weak draft, allowing it to go where other boats cannot.
  • The opportunity to get stuck into a book, nap on the deck with a warm sea breeze, or trampoline on the netting that sits at the front of the boat.
  • A catamaran is more stable than a sailboat, therefore they are a great way for first time sailors to discover the magic of sailing holidays, without the fear of seasickness!
  • A catamaran usually has 4 large cabins, which will allow you to cast off with your family or your best friends, with plenty of space for all.
  • The best way to discover the exotic islands of the Caribbean, including the Grenadines, Martinique, Guadeloupe, Cuba, and the British Virgin Islands.

Everything you need to know to organise your next catamaran sailing holiday

The advantages of a catamaran sailing holiday with Skipper

If you have an existing group of travellers (of family or friends), we highly recommend reserving an entire catamaran with skipper. In such cases, it is often possible to receive a discount on you booking (from 10% of the total booking cost upwards), this is more likely to be the case if you are booking in advance or in less busy periods of the year. In addition to saving money, reserving a skippered catamaran allows you maximum flexibility in itineraries, with skippers often willing to be very accommodating to your wishes. Reserving a whole catamaran also allows maximum privacy, if you are looking to share some quality time with your family or friends.

If you are travelling as a couple or solo, bare in mind that you can book either a single berth or an entire cabin. A cabin allows for much more privacy and more personal space. Either way, you have the ability to share your sailing experience with other like-minded travellers - an excellent opportunity to meet new people and make new friends!

Catamarans: the comfort of a house, on the water!

Many describe catamarans as floating houses, for the extensive space and facilities they have onboard. After a long day of adventure, you can rest in large, well-equipped cabins, that are complete with a full size double bed. There are usually 2 cabins each for the 2 floats, or sides of the boat. These are then separated by a bathroom, complete with a shower and toilet. The common area of the catamaran including the lounge and kitchen are then located in the middle-upper part of the boat, in between each float.

Catamarans are generally very spacious and bright, with large windows that overlook the sea, a perfect view when cooking or relaxing! They are very social and friendly due to how the design of the boat. Finally, it is true that the bridge offers lots of charm to the catamaran, this area of the boat is the main area for relaxing and enjoying time on the deck!

What are the differences between a sailboat or catamaran?

A sailboat may be better for people looking to learn the practice of sailing, or to sharpen their skills, where as the catamaran is the most comfortable and luxurious way to enjoy a holiday at sea. Here are a few advantages and disadvantages of each:

Sailboat: ideal for sailing, less emphasis on comfort, cheaper, less spacious, more user-friendly

Catamaran: less motion impact on the stability of the boat, more comfortable, more expensive, more spacious

The 8 best destinations for a catamaran sailing holiday

The Mediterranean, Caribbean, Indian oceans - some destinations are ideal for a skippered catamaran sailing holiday. For those who dream of a trip in the Caribbean, it is full of ideal different destinations for a catamaran trip. We mainly recommend the Grenadines (which normally set sail from the port of Marin in Martinique), Guadeloupe, and Cuba.

The Mediterranean Sea is another paradise for catamaran trips. We recommend a week between Corsica and Sardinia to explore the famous Lavezzi Islands and the Maddalena Archipelago, but there is also the wonderful Greek archipelago of the Cyclades or the Ionian Islands. Last but not least, who does not dream of discovering the paradisiacal landscapes of Seychelles aboard the catamaran with a local skipper? An adventure to treasure for your entire life.

All you need to know for your next skippered catamaran cruise

The demand for skippered catamaran holidays can be very high compared to the number of offers. We recommend booking several months in advance - January or February for summer trips in the Mediterranean and September or October for winter trips in the Caribbean.The best time for a catamaran holiday in the Mediterranean is from May to October. For a Caribbean holiday, between November and April.

The price of a catamaran sailing holiday can be much higher than a sailing holiday on a monohull because of the extra comfort and the limited availability. You can find experiences between €600 and €1,200 per week depending on the destination and the period of the year.

The best destinations for catamaran holidays are: Antilles (Grenadines, Guadeloupe, Cuba, British Virgin Islands), Seychelles and the Mediterranean (Greece, Corsica, Sardinia, Croatia). Booking an entire catamaran with a skipper is a brilliant option for holidays with family or friends.

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