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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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4.4

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

19 departures available

June - December

Starting from

€1,250

Per person - min 2 pax

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4.4

Catamaran cruise in the Saronics: between history and crystal clear sea

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

July - August

Starting from

€1,300

Per person

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4.4

Premium

BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

36 departures available

January - December

Starting from

€1,535

€1,382

Per person - min 2 pax

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5.0

Ibiza by catamaran with hostess

Spain: The Balearic Islands

7 days - 7 nights

One departure available

July

€1,870

Per person

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4.4

Premium

RAIATEA - TAHITI Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

15 departures available

January - December

Starting from

€2,330

Per person - min 2 pax

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4.4

Stellar Aegadian Islands aboard a catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,550

Per person

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4.6

Premium

Seychelles by Catamaran: Cabin Cruise with Full Board

Indian Ocean: Seychelles

7 days - 7 nights

21 departures available

June - November

Starting from

€1,675

Per person - min 2 pax

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4.4

Premium

BORA BORA PARADISE - Mini catamaran cruise with hostess and full board

Pacific Ocean: French Polynesia

4 days - 4 nights

One departure available

October

Starting from

€2,305

Per person - min 2 pax

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New

Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

8 departures available

July - October

Starting from

€238

Per person

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3.9

6 days in Costa Smeralda and Northern Sardinia

Italy: Northern Sardinia

5 days - 5 nights

5 departures available

June - August

Starting from

€1,100

€990

Per person

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Aeolian Islands by sailboat: 6 days between volcanoes and clear waters

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€6,950

Per person

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4.4

Classical Greece between Mythology and Nature by catamaran

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,350

Per person

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

1307 reviews

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!

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

06/8/2026

Daniel L.

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US

Everything was fabulous! Julien and Eric were exceptional! Food was fantastic. Boat rides were smooth and seemless. agenda was executed to perfection. loved it. we got lucky and were the only ones on the cruise. not so sure would have been as relaxing with 10 other people. But our experience was fantastic!
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June 2 long weekend on a catamaran in the Cinque Terre

06/7/2026

LUCA M.

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IT

what can I say ... formally it was only 96 hours along the Ligurian Levante ... but on the sea time passes along like the waves and on board Cassiopeia navigation envelops you as gently as the wind towards the coast ... But what turned a long weekend into a special experience was a set of ingredients... a nice crew with intelligent children attracted more by the sea than by a tablet ... A comfortable and spacious catamaran ... but above all Antonio, a captain who makes the difference by pampering the crew, preparing delicious food and always sailing in total safety: absolutely recommended!
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The magic of the Egadi Islands aboard a brand new catamaran

06/2/2026

Kris D.

-

BE

Amazing islands, flexible chartered, professional skipper.

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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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