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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!

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Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

5 departures available

September - October

Starting from

€2,150

Per person

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

2 departures available

September - October

Starting from

€950

Per person

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4.7

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

Italy: Northern Sardinia

7 days - 7 nights

39 departures available

April - November

Starting from

€1,640

€1,558

Per person - min 2 pax

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5.0

Super!

Weekend catamaran in Portovenere and Cinque Terre

Italy: Liguria

3 days - 2 nights

One departure available

September

€212

Per person

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4.7

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Seychelles by Catamaran: Cabin Cruise with Full Board

Indian Ocean: Seychelles

7 days - 7 nights

37 departures available

January - December

Starting from

€1,760

Per person - min 2 pax

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4.8

Super!

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

Starting from

€900

Per person

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4.8

Super!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

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4.7

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

October - November

€1,000

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

2 departures available

September

€850

Per person

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4.5

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

64 departures available

January - December

Starting from

€1,290

€1,161

Per person - min 2 pax

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4.5

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GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

44 departures available

January - December

Starting from

€1,680

€1,344

Per person - min 2 pax

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4.5

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ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

26 departures available

May - October

Starting from

€1,305

€1,044

Per person - min 2 pax

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

1464 reviews

Sail to the Aeolian Islands with an experienced crew on a catamaran!

09/5/2026

serena s.

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IT

One of the most beautiful charter cruises ever done! Enchanting Aeolian Islands. Catamaran [hidden] very welcoming, fantastic skippers and great food on board. Nothing was missing. I would leave with them tomorrow ... Highly recommended
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

09/3/2026

Francesca L.

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IT

Overall, I liked the experience, but I would have preferred more attention and care in the organization of travel, group moments and, above all, moments dedicated to the sea. Unfortunately, due to some organizational shortcomings on the part of the Different Sailing staff, I feel that it was not possible to fully enjoy the experience. The boat was also delivered to us late and in less than optimal condition: it was not particularly clean and in the following days we had to take care of the cleaning ourselves. As for the holiday itself, however, it was a lot of fun, especially thanks to our crew, made up of wonderful people who helped make the experience much better. However, it should also be noted that, initially, a maximum of 10 people per boat was expected, while in the end we found ourselves in 13, without having been adequately informed of the change. In my opinion, 13 people were a bit too many for the available space and this inevitably affected the comfort on board. Ultimately, I can't say that the experience was totally negative, because the group and the people I met made the holiday enjoyable. However, considering the organizational aspects and the condition of the boat, we will probably choose another company rather than Different Sailing in the future.
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The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

09/1/2026

Valerio F.

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IT

It was my first sailing trip and it definitely won't be the last!
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Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/1/2026

sofia l.

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IT

We spent a very special week on the catamaran! Giorgio, our skipper, was simply fantastic: competent, professional and always ready to make us live every moment to the fullest. He was helpful and patient, attentive to our needs and able to convey security and tranquility throughout the week. Thanks to him we were able to fully enjoy the trip, letting ourselves be carried away by the wonders of the Aeolian Islands. Our cook was equally exceptional. Prepared, tidy and impeccable in cleanliness, always available to meet any of our needs. It has been able to satisfy everyone even in the presence of special dietary needs, preparing alternatives suitable for both a celiac and a lactose intolerant. He cooked with true passion, giving us delicious dishes and always different, well-finished and surprising recipes every day. Eating on board was truly one of the pleasures of the holiday! What made everything even more special was the group that was created on board: we were lucky enough to share this experience with wonderful travel companions, always ready for a pleasant chat, a SUP ride or to share a glass of wine at sunset. The Aeolian Islands are beautiful, but thanks to your attention, your availability and the atmosphere you have helped to create, they have become truly unforgettable for us. ❤️

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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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