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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!

Northern Sardinia and Corsica in a comfortable Catamaran

Italy: Northern Sardinia

7 days - 7 nights

One departure available

August

€1,850

Per person

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4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,000

Per person

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4.8

Super!

From Palermo to Marsala: magical week on a catamaran with hostess

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,450

Per person

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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

4 departures available

June - September

Starting from

€1,050

Per person

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4.4

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

21 departures available

January - December

Starting from

€1,250

€1,125

Per person - min 2 pax

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4.8

Super!

Holiday in the Aeolian Islands on a catamaran: sea, sun, relaxation

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€1,380

Per person

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4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

16 departures available

June - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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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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4.8

Super!

Catamaran experience in Montenegro

Montenegro: Montenegro

7 days - 7 nights

4 departures available

July - August

€1,700

Per person

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4.8

Super!

Greek Islands Catamaran Cruise - Saronic

Greece: Saronic Islands and Athens area

7 days - 7 nights

12 departures available

June - October

Starting from

€820

Per person

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4.8

Super!

Catamaran with Chef in the magical sea of the Ionian Islands - Holiday for SINGLES

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,450

Per person

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4.8

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

15 departures available

June - November

Starting from

€1,000

Per person

Why book a holiday with Sailsquare?

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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

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

1310 reviews

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Catamaran with chef in the magical sea of the Ionian Islands

06/21/2026

Lorenzo G.

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GB

We had an amazing catamaran holiday in Greece. The places we visited were absolutely stunning, with crystal-clear waters, beautiful beaches, and unforgettable scenery. The catamaran was fantastic, comfortable, well-maintained, and perfect for exploring the Greek islands. A special thank you to our skipper and hostess, who made the entire experience exceptional. Their professionalism, kindness, and attention to detail created a relaxed and enjoyable atmosphere throughout the trip. The food was delicious, and every meal was prepared with great care. Another highlight was sharing this adventure with such a wonderful international group of fellow travellers. It was a pleasure meeting people from different countries and creating great memories together. Thank you to our skipper and hostess for the excellent sailing, the wonderful cuisine, and for making this such a memorable holiday. We would highly recommend this experience and would gladly do it again.
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Northern Sardinia and Corsica in a large and comfortable Catamaran

06/19/2026

Lorenzo L.

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IT

Fantastic holiday from every point of view. The charter unfolds in one of the most evocative locations in the Mediterranean within marine and terrestrial parks. The Lagoon 50 offers comfort on board not comparable to any monohull and nothing is missing among the equipment: tender, SUP, sofas and sundecks, a crazy kitchen and really beautiful cabins.... + comfortable than at home. The transfers were both motor and sailing and in the latter case the experience is truly memorable, 10 knots of effortless speed. The logistics in the port, embarkation and disembarkation were impeccable. The week is perfectly balanced between moments at sea and visits and leisure on land. Maurizio - the skipper and owner - is a host who always makes you feel at ease, very helpful, nice and prepared; I have always had excellent communication. Charter highly recommended! LL
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Northern Sardinia and Corsica in a large and comfortable Catamaran

06/18/2026

Mauro L.

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IT

Probably one of the most beautiful holidays of my life, a wonderful boat in some of the most beautiful places in Italy (but perhaps also in the world ..) with fantastic people. Maurizio proved to be an excellent skipper always ready and prepared to do everything possible to make a normal holiday into an unforgettable holiday, Peace, relaxation, crystal clear waters, perfect weather... I couldn't have asked for more. experience to be replicated next year, thank you!!

Four days among the islands of the Gulf of Naples

06/8/2026

Eleonora S.

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IT

For our first catamaran experience we chose Angelo and his [hidden] and we couldn't have made a better choice! A helpful and experienced captain, who made us discover the most beautiful bays of Procida and Ischia. Together with him, the cook Diego who satisfied all our requests with incredible kindness! We are super satisfied and hope to leave soon with them! [hidden] is beautiful and very well-kept, convenient even for those who, like us, had no experience of boat holidays!

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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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