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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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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

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

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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

1483 reviews

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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

09/9/2026

Giovanna G.

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IT

I must say that everything went very well! First experience in the flotilla and it was super! I recommend to all those who want to have a fun-filled holiday!

Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/9/2026

Vincenzo F.

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IT

Fantastic week. Perfect organization, hospitality and kindness are guaranteed. Giorgio and Diego excellent "hosts".
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Aeolian Islands on a catamaran, professional skipper/hostess, what else?

09/8/2026

Stefania P.

A week on a catamaran in the Aeolian Islands that I will hardly forget! ⛵️🌊 Andrea, our skipper, and Arianna, our hostess, were just amazing. Andrea is a real guarantee: competent, quiet and solid, he knows the Aeolian Islands and their sea like the back of his hand. He took us to discover wonderful places making us feel always in excellent hands. Arianna was very attentive to everything and everyone, always present and available. It was enough for someone to pronounce the word "beer?" and Arianna had already uncorked and made cheese, olives and taralli appear. They definitely spoiled us even at the table: delicious fish, pasta, vegetables, salads, wine... We really didn't miss anything. We discovered the Aeolian Islands from a wonderful perspective: during the day from the sea, between bays, dives and incredible views, and in the evening going ashore for a walk, a granita or an aperitif. One of the moments that I will definitely take with me is Stromboli: the sea crossing at sunset and the spectacle of the Sciara del Fuoco seen from the catamaran were exciting and evocative, difficult to describe in words. To make this holiday even more special was also the group I was lucky enough to find. People who a week earlier were strangers and with whom, between laughter, life on a boat, aperitifs and shared moments, a beautiful understanding was created. I left for a week in the Aeolian Islands and came back with many more memories than I thought I would pack. ❤️ Thank you Andrea, Arianna and the whole group for making this experience so special. I would do it again tomorrow! Greetings from Paris 😉
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Capri, Ischia and Amalfi Coast by catamaran with hostess and cook

09/8/2026

Valentina A.

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IT

We really enjoyed our time. The boat was brand new and super spacious, with very large rooms. Air conditioning, especially during such a hot summer, was really essential. The skipper Alessio was always very kind and willing to meet our needs, as well as the two girls of the crew, who took care of the cleaning, the kitchen and also the maneuvers. The food was also great and having someone take care of the galley, cooking and cleaning is a luxury that really makes a difference on a boat. We liked the Amalfi Coast, even if honestly it did not particularly excite us. In our opinion, this type of holiday could be enhanced even more by itineraries such as Sardinia or Greece, which we also know from experience. The only advice I would give to Alessio is to provide a briefing with the basic information before departure, especially to help those who have never taken a boat holiday. For the rest, really positive experience!

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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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