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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

4 departures available

October

Starting from

€2,250

Per person

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4.7

Premium

Seychelles by Catamaran: Cabin Cruise with Full Board

Indian Ocean: Seychelles

7 days - 7 nights

33 departures available

January - December

Starting from

€1,760

Per person - min 2 pax

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4.9

Super!

Caribbean Escape – Sailing the Grenadines

Caribbean: Grenadines & Martinique

10 days - 10 nights

2 departures available

January - February

€2,100

Per person

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4.4

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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

€1,440

€1,152

Per person - min 2 pax

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4.4

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

Caribbean: Grenadines & Martinique

9 days - 10 nights

43 departures available

January - December

Starting from

€1,840

€1,472

Per person - min 2 pax

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4.4

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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

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4.4

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ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

20 departures available

January - December

Starting from

€1,520

€1,292

Per person - min 2 pax

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4.4

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CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

26 departures available

May - October

Starting from

€1,320

€1,056

Per person - min 2 pax

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5.0

New

Discover the wonderful coasts and villages of the Balearic Islands by trimaran

Spain: The Balearic Islands

7 days - 7 nights

2 departures available

October

€850

Per person

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4.4

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CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

One departure available

October

Starting from

€1,485

Per person - min 2 pax

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4.4

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GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

53 departures available

January - December

Starting from

€1,400

€1,120

Per person - min 2 pax

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4.4

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BAHAMAS EXUMA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

6 days - 7 nights

50 departures available

January - December

Starting from

€1,940

€1,552

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

1521 reviews

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Luxury catamaran cruise in the Cyclades

09/30/2026

Sofi B.

-

GB

10/10 holiday, this is the best way to travel
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Weekend catamaran in Portovenere and Cinque Terre

09/29/2026

Coretta P.

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IT

Antonio proved to be a very knowledgeable, organized, helpful and patient owner/skipper. The catamaran was found to be particularly comfortable and well maintained. Splendid itinerary and the weather also favored us. In short, a beautiful weekend!

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

09/29/2026

Sergio V.

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IT

Alessandro is first of all a great person, then as far as the week is concerned he proved to be available and attentive to the requests and desires of the crew, precious for suggestions and advice on what to do. He always accompanied us even on the ground. Helena, passionate about her work, has always prepared different dishes that are satisfying for the taste and for the eyes. It couldn't have been better than this!

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/29/2026

Gloris M.

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IT

We had a wonderful week. The skipper Fabrizio, always very kind, made us feel safe with great professionalism and tried to satisfy all our requests compatibly with the weather. The hostess Monica, always discreet and patient, knew how to take care of the guests without being intrusive. He prepared tasty dishes that helped make the holiday even more enjoyable. If we could we would leave immediately for another holiday with this crew!

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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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