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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.

73

experiences

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Discovering the Aeolian Islands by catamaran with hostess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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34 travellers

Starting from

€1,250

Per person

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4.8

Super!

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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24 travellers

Starting from

€1,150

Per person

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4.8

Super!

Dream sailing on a fully-equipped catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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5 travellers

Starting from

€940

Per person

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4.6

From the Gulf of Corinth to the Sporades on my catamaran

Duration:

7 days - 7 nights

Greece:

North Egean Islands

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2 travellers

€750

Per person

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5.0

Kornati Islands: a week on a catamaran among the pearls of Croatia

Duration:

7 days - 7 nights

Croatia:

Kornati Islands

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20 travellers

Starting from

€1,400

Per person

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4.8

Super!

Dream sailing on a fully-equipped catamaran

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

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3 travellers

Starting from

€850

Per person

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5.0

Capri and the Amalfi Coast by catamaran with skipper and hostess

Duration:

7 days - 7 nights

Italy:

Naples & Amalfi Coast

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6 travellers

€1,000

Per person

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4.8

Super!

From Elba to the Maddalena Archipelago and Olbia

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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3 travellers

€790

Per person

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4.8

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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49 travellers

Starting from

€950

Per person

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3.2

11 days to discover the Aeolian Islands in company

Duration:

11 days - 11 nights

Italy:

Aeolian Islands

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5 travellers

Starting from

€1,802

Per person

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4.3

Catamaran ride in the sea of Ulysses

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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31 travellers

Starting from

€1,125

Per person

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4.6

From Thrace to Limnos by catamaran

Duration:

7 days - 7 nights

Greece:

North Egean Islands

Give this experience a try!

€870

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

1018 reviews

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Weekend catamaran in Portovenere and Cinque Terre

05/12/2025

Davide S.

-

Italy

Antonio ed il suo catamarano "Cassiopea" sono il perfetto mix tra compentenza, professionalità, freschezza, passione e disponibilità nel far sentire gli ospiti a loro agio durante tutta la permanenza in barca. Semplicemente quello che serve per staccare la spina dalla frenesia quotidiana e trascorrere dei bei momenti in mare in ottima compagnia. Super consigliato.
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PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

05/9/2025

Sara Angela R.

Ho partecipato a una crociera in catamarano con skipper e cuoco, ma purtroppo l’esperienza non è stata all’altezza delle aspettative. La destinazione e l’itinerario proposto sono davvero splendidi, così come la cucina a bordo, che è stata un punto di forza. Anche il modello dell’imbarcazione è di grande fascino, ma la barca non era in condizioni ottimali: l’aria condizionata funzionava a intermittenza, c’erano infiltrazioni d’acqua in cabina, e nel complesso non offriva il livello di comfort e lusso promesso. L’equipaggio, in particolare lo skipper, si è mostrato freddo e poco comunicativo, al punto che spiegare le tappe o semplicemente rivolgergli una domanda sembrava quasi un disturbo. Questo ha reso l’esperienza a bordo piuttosto piatta e poco coinvolgente. In sintesi, nonostante la bellezza dei luoghi visitati e la buona cucina, il servizio e le condizioni della barca non giustificano il prezzo pagato. Rapporto qualità/prezzo deludente.
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Seychelles paradise by Catamaran

05/6/2025

Fabrizio P.

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Italy

una settimana in catamarano alle Seychelles con equipaggio italiano è pura magia. Ciccio il capitano Peppe vicecapitano e Claudia la cuoca. Accoglienza impeccabile, mare turchese e spiaggie da cartolina. Ospiti Toooooopppppp.
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ELBA ISLAND - Weekend in Catamaran Lagoon 42 - Departure from Piombino

05/6/2025

Debora C.

-

Italy

Bellissimo catamarano molto confortevole

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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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